73 results on '"Humayun Pervez"'
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2. Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones
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Muhammad Yaqub, Mohammad Saeed Iqbal, Humayun Pervez, Naveeda Saira, and Khalid Mohammed Khan
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isatin ,5-trifluoromethoxyisatin ,thiosemicarbazones ,5-trifluoromethoxyisatin-3-thiosemicarbazones ,toxicity ,Organic chemistry ,QD241-441 - Abstract
A series of twenty one N4-aryl substituted 5-trifluoromethoxyisatin-3-thiosemicarbazones 3a-3u was synthesized by the reaction of trifluoromethoxyisatin 1 with different arylthiosemicarbazides 2 in aqueous ethanol (50%), containing a few drops of acetic acid. Their structures were established on the basis of analytical (CHN) and spectral (IR, 1H-NMR, EIMS) data. All the synthesized compounds were evaluated for their toxicity potential by a brine shrimp lethality bioassay. Ten compounds i.e., 3a, 3e, 3i-3l and 3n-3q proved to be active in this assay, displaying promising toxicity (LD50 = 1.11 × 10−5 M − 1.80 × 10−4 M). Amongst these, 3k, 3n and 3o were found to be the most active ones (LD50 = 1.11 × 10−5 M − 1.43 × 10−5 M). Compound 3k showed the highest activity with a LD50 value of 1.11 × 10−5 M and can, therefore, be used as a lead for further studies. Structure-activity relationship (SAR) studies revealed that the presence of strong inductively electron-attracting trifluoromethoxy substituent at position-5 of the isatin moiety played an important role in inducing or enhancing toxic potentiality of some of the synthesized compounds.
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- 2011
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3. (2Z)-N-(2-Chlorobenzyl)-2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)hydrazinecarbothioamide
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Humayun Pervez, Nazia Khan, Mohammad S. Iqbal, Muhammad Yaqub, and M. Nawaz Tahir
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Crystallography ,QD901-999 - Abstract
In the title compound, C16H13ClN4OS, the isatin ring system is oriented at dihedral angles of 10.60 (7) and 72.60 (3)° with respect to the thiosemicarbazide and 2-chlorobenzyl groups, respectively. The near planarity of the isatin and thiosemicarbazide groups [r.m.s. deviations of 0.0420 and 0.0163 Å, respectively] is reinforced by intramolecular N—H...O and N—H...N hydrogen bonds, which generate S(6) and S(5) rings, respectively. In the crystal, inversion dimers linked by pairs of N—H...O hydrogen bonds generate R22(8) loops. Aromatic π–π stacking interactions between the centroids of heterocyclic five-membered and benzene rings [distance = 3.6866 (11) Å] are also observed.
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- 2012
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4. (Z)-4-(3-Fluorophenyl)-1-(5-nitro-2-oxoindolin-3-ylidene)thiosemicarbazide
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Muhammad Yaqub, Nazia Manzoor, Humayun Pervez, and M. Nawaz Tahir
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Crystallography ,QD901-999 - Abstract
In the title compound, C15H10FN5O3S, an intramolecular N—H...N hydrogen bond generates an S(5) ring, whereas N—H...O and C—H...S interactions complete S(6) ring motifs. The dihedral angle between the isatin ring system and the fluorobenzene ring is 5.96 (6)° and the complete molecule is close to planar (r.m.s. deviation for all the non-H atoms = 0.112 Å). In the crystal, molecules are linked by N—H...O hydrogen bonds to form C(8) chains along the [100] direction and C—H...O interactions are also observed.
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- 2012
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5. 4-(3-Fluorophenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide
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Muhammad Yaqub, M. Nawaz Tahir, Humayun Pervez, and Muhammad Ramzan
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Crystallography ,QD901-999 - Abstract
In the title compound, C15H11FN4OS, there are three independent molecules, each with a disordered 3-fluorophenyl group [occupancy ratios = 0.547 (17):0.453 (17), 0.645 (5):0.355 (5) and 0.626 (15):0.374 (15)] and displaying dihedral angles of 4.2 (3), 25.2 (6) and 32.4 (5)° between the 2-oxoindoline and fluoro-substituted phenyl rings. Strong intramolecular N—H...N and N—H...O and weak intramolecular C—H...S hydrogen bonds complete S(5) and S(6) ring motifs, while strong intermolecular N—H...O hydrogen bonds interconnect the three independent molecules through R33(12) ring motifs. The three-molecule units are in turn linked into polymeric sheets via C—H...F and C—H...S hydrogen bonds and π–π interactions [centroid–centroid distances in the range 3.520 (2)–3.820 (9) Å].
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- 2010
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6. 1-(2-Oxoindolin-3-ylidene)-4-[2-(trifluoromethoxy)phenyl]thiosemicarbazide
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Muhammad Ramzan, Humayun Pervez, M. Nawaz Tahir, Muhammad Yaqub, and Mohammad S. Iqbal
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Crystallography ,QD901-999 - Abstract
The crystal structure of the title compound, C16H11F3N4O2S, is stabilized in the form of polymeric chains by N—H...O interactions. In the molecular structure, two S(5) ring motifs are formed by intramolecular N—H...N and N—H...O hydrogen bonding and two S(6) rings are present due to N—H...O and C—H...S interactions. π–π interactions are present with distances of 3.2735 (17), 3.563 (2) and 3.664 (4)/3.688 (3) Å between the centroids of the heterocyclic rings, between the centroids of the heterocyclic ring and trifluoromethoxy-substituted phenyl ring, and between the centroids of the trifluoromethoxy-substituted phenyl rings, respectively. The trifluoromethoxyphenyl group is disordered over two sites with an occupancy ratio of 0.642 (10):0.358 (10).
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- 2010
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7. 4-(3-Iodophenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide
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Humayun Pervez, Muhammad Yaqub, Muhammad Ramzan, and M. Nawaz Tahir
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Crystallography ,QD901-999 - Abstract
In the title compound, C15H11IN4OS, intramolecular N—H...N, N—H...O and C—H...S interactions generate one S(5) and two S(6) ring motifs. In the crystal, molecules form centrosymmetric dimers via pairs of N—H...O interactions, generating R22(8) ring motifs. In addition a short intermolecular I...S contact of 3.352 (3) Å is observed.
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- 2010
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8. 4-(2-Ethylphenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide
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Humayun Pervez, Muhammad Yaqub, Muhammad Ramzan, M. Nawaz Tahir, and Mohammad S. Iqbal
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Crystallography ,QD901-999 - Abstract
The title compound, C17H16N4OS, is stabilized in the form of a two-dimensional polymeric network due to intermolecular N—H...S and N—H...O hydrogen bonds. An intramolecular N—H...N hydrogen bond forms an S(5) ring, whereas interactions of the N—H...O and C—H...S types complete S(6) ring motifs. π–π interactions with a centroid–centroid distance of 3.6514 (10) Å are found between the ethyl-substituted benzene ring and the heterocyclic ring of the isatin derivative.
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- 2010
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9. 1-[2-Oxo-5-(trifluoromethoxy)indolin-3-ylidene]-4-[4-(trifluoromethyl)phenyl]thiosemicarbazide
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Humayun Pervez, Mohammad S. Iqbal, Naveeda Saira, Muhammad Yaqub, and M. Nawaz Tahir
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Crystallography ,QD901-999 - Abstract
In the title compound, C17H10F6N4O2S, an intramolecular N—H...N hydrogen bonds forms an S(5) ring whereas N—H...O and C—H...S interactions complete S(6) ring motifs. The dihedral angle between the fused ring system and the phenyl ring is 6.68 (8)°. In the crystal, the molecules are dimerized due to N—H...O interactions. π–π interactions are present between the benzene rings [centroid–centroid distance = 3.6913 (15) Å] and between the five membered ring and the trifluoromethyl)phenyl ring [centroids–centroid distance = 3.7827 (16) Å]. One of the trifluoromethoxy F atoms is disordered over two sites with occupancy ratio of 0.76 (3):0.24 (3). The F atoms of the p-trifluoromethyl substituent are disordered over three sets of sites with an occupancy ratio of 0.70 (2):0.152 (11):0.147 (13).
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- 2010
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10. N-{2-[N-(4-Methylphenyl)oxamoyl]phenyl}propanamide
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Humayun Pervez, Maqbool Ahmad, Muhammad Yaqub, M. Nawaz Tahir, and Naveeda Saira
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Crystallography ,QD901-999 - Abstract
The title compound, C18H18N2O3, is the product of the heterocyclic ring cleavage at position 2 of 1-propionylisatin. Two centrosymmetric cyclic motifs, viz. R22(14) and R22(18), are formed by N—H...O hydrogen bonds with the propanamide and aminophenyl units, respectively, as the N—H donors. These motifs combine into two C22(8) chain motifs parallel to the b axis. The chain structure is stabilized by C—H...π interactions between the benzene rings, where C—H is from the phenyl ring of the cleaved part of 1-propionylisatin.
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- 2010
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11. 1-Acetyl-3-[2-(2,3,5,6-tetrafluorophenyl)hydrazin-1-ylidene]indolin-2-one
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Humayun Pervez, Muhammad Yaqub, Maqbool Ahmad, M. Nawaz Tahir, and Robina Akhtar
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Crystallography ,QD901-999 - Abstract
In the title compound, C16H9F4N3O2, the dihedral angle between the aromatic ring systems is 4.10 (14)° and a bifurcated intramolecular N—H...(O,F) hydrogen bond generates an S(6) ring for the O-atom acceptor and an S(5) ring for the F-atom acceptor. A short C—H...O conact also occurs. In the crystal, molecules are linked by C—H...O interactions.
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- 2010
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12. 1-[1-(4-Bromophenyl)ethylidene]-4-(2,4-dimethoxyphenyl)thiosemicarbazide
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Muhammad Yaqub, Humayun Pervez, Nadia Arif, M. Nawaz Tahir, and Mazhar Hussain
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Crystallography ,QD901-999 - Abstract
In the title compound, C17H18BrN3O2S, the dihedral angle between the aromatic rings is 9.15 (17)°. A bifurcated intramolecular N—H...(N,O) hydrogen bond generates two S(5) rings and a weak intramolecular C—H...S interaction completes an S(6) ring motif. In the crystal, inversion dimers linked by pairs of N—H...S hydrogen bonds generate R22(8) loops and weak C—H...S and C—H...π interactions are also present.
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- 2010
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13. 4-(3-Nitrophenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide
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Humayun Pervez, Mohammad S. Iqbal, Naveeda Saira, Muhammad Yaqub, and M. Nawaz Tahir
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Crystallography ,QD901-999 - Abstract
In the title compound, C15H11N5O3S, intramolecular N—H...N hydrogen bonding forms an S(5) ring motif, whereas N—H...O and C—H...S interactions type complete S(6) ring motifs. The 2-oxoindoline and 3-methoxyphenyl rings are almost planar, with r.m.s. deviations of 0.0178 and 0.0149 Å, respectively, and form a dihedral angle of 33.59 (3)°. In the crystal, molecules are interlinked through the nitro groups in an end-to-end fashion via N—H...O and C—H...O interactions.
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- 2010
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14. 4-(3-Methoxyphenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide
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Humayun Pervez, Mohammad S. Iqbal, Naveeda Saira, Muhammad Yaqub, and M. Nawaz Tahir
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Crystallography ,QD901-999 - Abstract
In the title compound, C16H14N4O2S, intramolecular N—H...N hydrogen bonding forms an S(5) ring, whereas N—H...O and C—H...S interactions complete S(6) ring motifs. In the crystal, molecules form inversion dimers due to N—H...O interactions. The dimers are interlinked through N—H...S hydrogen bonds and π–π interactions occur with a centroid–centroid distance of 3.8422 (11) Å between the methoxy-containing benzene ring and the five-membered heterocyclic ring.
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- 2010
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15. 4-(2-Fluorophenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide
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Humayun Pervez, Muhammad Yaqub, Muhammad Ramzan, Mohammad S. Iqbal, and M. Nawaz Tahir
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Crystallography ,QD901-999 - Abstract
The title compound, C15H11FN4OS, is almost planar, the dihedral angle between the aromatic ring systems being 5.00 (13)°. The conformation is stabilized by intramolecular N—H...N and N—H...O hydrogen bonds, which generate S(5) and S(6) rings, respectively. N—H...F and C—H...S interactions also occur. In the crystal, inversion dimers linked by pairs of N—H...O hydrogen bonds occur, generating R22(8) loops.
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- 2010
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16. 4-(5-Chloro-2-methylphenyl)-1-[2-oxo-5-(trifluoromethoxy)indolin-3-ylidene]thiosemicarbazide
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Humayun Pervez, Mohammad S. Iqbal, Naveeda Saira, Muhammad Yaqub, and M. Nawaz Tahir
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Crystallography ,QD901-999 - Abstract
The asymmetric unit of the title compound, C17H12ClF3N4O2S, contains two molecules, which differ in their planarity and hydrogen bonding. In one molecule, the 2-oxoindolin (C8/N/O A), thiosemicarbazide (N3/C/S B) and 5-chloro-2-methylphenyl (C7/Cl C) units are planar with r.m.s. deviations of 0.0110, 0.0173 and 0.0259 Å, respectively. The dihedral angles A/B, B/C and A/C are 1.74 (15), 40.70 (13) and 41.00 (11)°, respectively. In the other molecule the deviations are 0.0455, 0.0007 and 0.0143 Å, respectively, and the dihedral angles are 5.01 (14), 4.53 (16) and 3.38 (13)°, respectively. In both molecules, intramolecular N—H...N and N—H...O hydrogen bonds form S(5) and S(6) ring motifs, respectively and C—H...S interactions occur. In one of the molecules, an intramolecular C—H...F interaction is also present. In the crystal, the molecules are linked by N—H...O, C—H...F, C—H...O and N—H...S hydrogen bonding, forming a polymeric network.
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- 2010
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17. 1-(5-Nitro-2-oxoindolin-3-ylidene)-4-o-tolylthiosemicarbazide methanol monosolvate
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Humayun Pervez, Muhammad Yaqub, Nazia Manzoor, M. Nawaz Tahir, and M. Saeed Iqbal
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Crystallography ,QD901-999 - Abstract
In the title compound, C16H13N5O3S·CH4O, the dihedral angle between the isatin unit and the 2-methylphenyl group is 41.81 (2)° and intramolecular N—H...O and N—H...N hydrogen bonds occur, generating S(6) and S(5) rings, respectively. In the crystal, polymeric chains arise as a result of N—H...O, O—H...S and C—H...O interactions.
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- 2009
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18. (Z)-4-Hexyl-1-(5-nitro-2-oxo-2,3-dihydro-1H-indol-3-ylidene)thiosemicarbazide
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Humayun Pervez, Muhammad Yaqub, Nazia Manzoor, M. Nawaz Tahir, and M. Saeed Iqbal
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Crystallography ,QD901-999 - Abstract
In the title compound, C15H19N5O3S, intramolecular N—H...O, N—H...N and C—H...S interactions occur and the three terminal C atoms of the hexyl group are disordered over two sites with an occupancy ratio of 0.664 (12):0.336 (12). In the crystal, inversion dimers linked by pairs of N—H...O hydrogen bonds occur and C—H...O bonds link the dimers into chains. A short C=O...π contact is also present.
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- 2009
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19. Synthesis, crystal structure, molecular docking studies and bio-evaluation of some N 4-benzyl-substituted isatin- 3-thiosemicarbazones as urease and glycation inhibitors
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Nazia Khan, Muhammad Yaqub, Sumera Zaib, Muhammad Tahir, Muhammad Moazzam Naseer, Humayun Pervez, and Jamshed Iqbal
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Urease ,biology ,010405 organic chemistry ,Chemistry ,Isatin ,Organic Chemistry ,Crystal structure ,01 natural sciences ,Combinatorial chemistry ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,Glycation ,biology.protein - Abstract
Fifteen N 4-benzyl-substituted isatin-3-thiosemicarbazones 5a–o were synthesized and evaluated for their urease and glycation inhibitory potential. Lemna aequinocitalis growth and Artemia salina assays were also done to determine their phytotoxic and toxic effects. All compounds are potent inhibitors of the urease enzyme, displaying inhibition [half maximal inhibitory concentration (IC50)=1.08±0.12–11.23±0.19 μm] superior to that of the reference inhibitor thiourea (IC50=22.3±1.12 μm). Compounds 5c, 5d, 5h, 5j,k are potent antiglycating agents, showing glycation inhibitory activity better than that of the reference inhibitor rutin (IC50 values 209.87±0.37–231.70±6.71 vs. 294.5±1.5 μm). In the phytotoxicity assay, 11 thiosemicarbazones 5a–d, 5g, 5h, 5j–l, 5n,o are active, demonstrating 5–100% growth inhibition of L. aequinocitalis at the highest tested concentrations (1000 or 500 μg/mL). In the brine shrimp (A. salina) lethality bioassay, three derivatives 5b, 5j and 5o are active with median lethal dose (LD50) values of 3.63×10−5, 2.90×10−5 and 2.31×10−4 m, respectively.
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- 2018
20. Synthesis, X-ray molecular structure, biological evaluation and molecular docking studies of some N 4 -benzyl substituted 5-nitroisatin-3-thiosemicarbazones
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Muhammad Tahir, Muhammad Moazzam Naseer, Sumera Zaib, Humayun Pervez, Nazia Khan, Muhammad Yaqub, and Jamshed Iqbal
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Urease ,Stereochemistry ,Clinical Biochemistry ,Pharmaceutical Science ,Brine shrimp ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Drug Discovery ,Bioassay ,Molecular Biology ,chemistry.chemical_classification ,biology ,010405 organic chemistry ,Organic Chemistry ,Active site ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Enzyme ,Thiourea ,chemistry ,biology.protein ,Molecular Medicine ,Growth inhibition ,Artemia salina - Abstract
A series of fifteen N4-benzyl substituted 5-nitroisatin-3-thiosemicarbazones 5a–o was synthesized and evaluated for urease inhibitory, phytotoxic and cytotoxic influences. All the compounds proved to be highly potent inhibitors of the enzyme, showing inhibitory activity (IC50 = 0.87 ± 0.25–8.09 ± 0.23 μM) much better than the reference inhibitor, thiourea (IC50 = 22.3 ± 1.12 μM) and may thus act as persuasive leads for further studies. In phytotoxicity assay, twelve out of fifteen thiosemicarbazones tested i.e. 5a–e, 5g, 5i and 5k–o appeared to be active, exhibiting weak or non-significant (5–35%) growth inhibition at the highest tested concentrations (1000 or 500 μg/mL). In contrast, only one compound i.e. 5i was active in the brine shrimp (Artemia salina) lethality bioassay, demonstrating cytotoxic activity with LD50 value 2.55 × 10−5 M. Molecular docking studies of compounds 5a–o were also performed to identify their probable binding modes in the active site of the enzyme.
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- 2017
21. Synthesis, biological evaluation and docking studies of some novel isatin-3-hydrazonothiazolines
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Muhammad Yaqub, Sumera Zaib, Jamshed Iqbal, Maqbool Ahmad, Muhammad Moazzam Naseer, Humayun Pervez, and Shafiullah Khan
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chemistry.chemical_classification ,biology ,010405 organic chemistry ,Stereochemistry ,General Chemical Engineering ,Isatin ,General Chemistry ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,Enzyme ,chemistry ,Thiourea ,Docking (molecular) ,Bioassay ,Phytotoxicity ,Artemia salina ,IC50 - Abstract
A new series of thirty nine 5-trifluoromethoxy/fluoro/chloro-isatin 3-hydrazonothiazolines 5a–n, 6a–o and 7a–j were synthesized by cyclization of the corresponding intermediate N4-aryl-substituted isatin-3-thiosemicarbazones 3 (prepared by condensation of appropriate isatin 1 with appropriate N4-aryl-substituted 3-thiosemicarbazides 2) with 4-chlorophenacyl bromide 4 in absolute ethanol or ethanol–benzene mixture and screened for their cytotoxicity, phytotoxicity, antifungal and urease inhibitory potential. All the synthesized compounds were found to be almost inactive in a brine shrimp (Artemia salina) bioassay, demonstrating IC50 values > 1.62 × 10−4 to 2.17 × 10−4 M. In a phytotoxicity assay, out of thirty-nine compounds tested, six i.e. 5i, 6h, 6i, 6k, 7c and 7h proved to be active, showing weak or non-significant (5–30%) activity at the highest tested concentration (500 μg mL−1). Similarly, in antifungal assay, twenty-six compounds i.e. 5a, 5b, 5d–f, 5h–j, 5m, 6a, 6b, 6d, 6j, 6l–o, 7a, 7b and 7d–j were found to be active against one, two, or three selected fungal strains, exhibiting weak or non-significant inhibition (10–30%). Of these, 6d and 6o displayed a relatively better activity profile in terms of the number of organisms inhibited. On the other hand, in a urease inhibition bioassay, all the synthesized hydrazonothiazolines proved to be potent enzyme inhibitors, demonstrating inhibitory activity with IC50 values ranging from 3.70 ± 0.62 to 849 ± 2.26 μM. Compounds 5c, 5g–i, 5k, 5n, 6b, 6c, 6i, 6k, 6l, 6n, 6o, 7a, 7e, 7i and 7j were, however, found to be relatively very potent, displaying outstanding enzymatic activity (IC50 = 3.70 ± 0.62 to 20.9 ± 0.57 μM), even better than the reference inhibitor thiourea (IC50 = 22.3 ± 1.12 μM), and may thus act as valid leads for further studies. Molecular docking studies of the synthesized isatin–thiazolines 5a–n, 6a–o and 7a–j were also carried out to elucidate their relationship with the binding pockets of the enzyme. This study offers the first example of exhibition of urease inhibitory potential by isatin–thiazolines and as such provides a solid basis for further research on these compounds to develop more potent antiurease compounds of medicinal/agricultural interest.
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- 2016
22. Synthesis, cytotoxic and urease inhibitory activities of some novel isatin-derived bis-Schiff bases and their copper(<scp>ii</scp>) complexes
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Maqbool Ahmad, Jamshed Iqbal, Sumera Zaib, Muhammad Moazzam Naseer, Humayun Pervez, and Muhammad Yaqub
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Pharmacology ,chemistry.chemical_classification ,Schiff base ,010405 organic chemistry ,Stereochemistry ,Isatin ,Organic Chemistry ,Sulforhodamine B ,Pharmaceutical Science ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry.chemical_compound ,Enzyme ,chemistry ,Thiourea ,Drug Discovery ,Molecular Medicine ,Cytotoxic T cell ,Cytotoxicity ,IC50 - Abstract
Several isatin-3-thiosemicarbazones (a class of Schiff bases) from our earlier studies have been validated as promising cytotoxic agents and urease inhibitors. Also, a number of isatin-derived imines (Schiff bases) and their Cu(II) complexes have been reported in the literature to exhibit potential cytotoxic activity towards different cells. In view of this, a series of seven new 5-(un)-substituted isatin-derived bis-Schiff bases/ligands 3a–g and their Cu(II) complexes 5a–g were synthesized and evaluated for their cytotoxic and urease inhibitory activities. All the Schiff base ligands 3a–g proved to be active in sulforhodamine B (SRB) bioassay, displaying promising cytotoxic activity against lung carcinoma (H157) cells. Compound 3b was found to be the most potent inhibitor of H157 cells, exhibiting an IC50 value of 2.32 ± 0.11 μM. Similarly, all the metal complexes 5a–g proved to be active in this assay, demonstrating enhanced cytotoxic activity in each case, occurring as a result of coordination of the Schiff base ligands to the metal ion. Compound 5d proved to be the most potent inhibitor of H157 cells, showing cytotoxic activity comparable to that of the standard drug, vincristine (VCN) (IC50 = 1.29 ± 0.06 vs. 1.03 ± 0.04 μM). In the urease inhibition assay, all the synthesized Schiff base ligands except 3f proved to be highly potent enzyme inhibitors, displaying inhibitory activity even better than that of the reference inhibitor, thiourea (IC50 = 0.04 ± 0.004–5.86 ± 0.09 vs. 22.3 ± 1.12 μM), and thus may act as promising lead molecules for further studies. Molecular docking studies were also carried out for bis-Schiff bases 3a–g to elucidate their relationship with the binding pockets of the enzyme.
- Published
- 2016
23. Synthesis and in vitro Bio-activity Evaluation of N4-benzyl Substituted 5-Chloroisatin-3-thiosemicarbazones as Urease and Glycation Inhibitors
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Nazia Khan, Muhammad Yaqub, Jamshed Iqbal, Sumera Zaib, Muhammad Moazzam Naseer, and Humayun Pervez
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Isatin ,Thiosemicarbazones ,Urease ,Protein Conformation ,Rutin ,Heterocyclics ,010402 general chemistry ,01 natural sciences ,lcsh:Chemistry ,chemistry.chemical_compound ,Structure-Activity Relationship ,Glycation ,Heterocyclic Compounds ,Polysaccharides ,Structure–activity relationship ,Animals ,Araceae ,Amino Acid Sequence ,Amino Acids ,Enzyme Inhibitors ,Cytotoxicity ,Binding Sites ,biology ,Molecular Structure ,010405 organic chemistry ,biology.organism_classification ,0104 chemical sciences ,Molecular Docking Simulation ,lcsh:QD1-999 ,chemistry ,Thiourea ,5-Chloroisatin ,Glycation inhibition ,biology.protein ,Schiff bases ,Phytotoxicity ,Urease inhibition ,Artemia salina ,Artemia ,Nuclear chemistry ,Protein Binding - Abstract
A series of fifteen N4-benzyl substituted 5-chloroisatin-3-thiosemicarbazones 5a–o were synthesized and screened mainly for their antiurease and antiglycation effects. Lemna aequinocitalis growth and Artemia salina assays were carried out to determine their phytotoxicity and cytotoxicity potential. All the compounds proved to be extremely effective urease inhibitors, demonstrating enzyme inhibition much better than the reference inhibitor, thiourea (IC50 values 1.31 ± 0.06 to 3.24 ± 0.15 vs. 22.3 ± 1.12 μM). On the other hand, eight out of fifteen compounds tested, i.e. 5b, 5c, 5h–k, 5m and 5n were found to be potent glycation inhibitors. Of these, five viz. 5c, 5h–j and 5n proved to be exceedingly efficient, displaying glycation inhibition greater than the reference inhibitor, rutin (IC50 values 114.51 ± 1.08 to 229.94 ± 3.40 vs. 294.5 ± 1.5 μM).
- Published
- 2018
24. Synthesis of hexacyclic fused isocoumarin framework through selective domino multicyclizations under catalyst and solvent free conditions
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Muhammad Moazzam Naseer, Tariq Mahmood Babar, Muhammad Rauf, Masahiro Ebihara, Nasim Hasan Rama, and Humayun Pervez
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Reaction conditions ,Solvent free ,Chemistry ,General Chemistry ,Combinatorial chemistry ,Chloride ,Domino ,Stereocenter ,Catalysis ,Isocoumarin ,chemistry.chemical_compound ,Yield (chemistry) ,medicine ,medicine.drug - Abstract
A novel fused isocoumarin skeleton has been synthesized through selective domino multicyclizations by mixing homothallic acid and 2,3-diphenylacryloyl chloride at 200 °C under catalyst and solvent free reaction conditions. Six fused rings with two stereogenic centers were assembled in a convenient one-pot operation in good yield. The resulting hexacyclic fused isocoumarin skeleton and its stereochemistry was fully characterized and unambiguously confirmed by X-ray diffraction analysis.
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- 2014
25. Synthesis and solid state self-assembly of an isatin–thiazoline hybrid driven by three self-complementary dimeric motifs
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Maqbool Ahmad, Loïc Toupet, Muhammad Moazzam Naseer, Humayun Pervez, and Taibi Ben Hadda
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Stereochemistry ,Isatin ,Thiazoline ,Organic Chemistry ,Solid-state ,Supramolecular chemistry ,Biochemistry ,Layered structure ,chemistry.chemical_compound ,Crystallography ,chemistry ,Drug Discovery ,Molecule ,Self-assembly - Abstract
An interesting isatin–thiazoline hybrid molecule having C N N N bonds has been synthesized and its solid state self-assembly behaviour was studied by X-ray diffraction technique. A layered structure based on hexameric supracycles, which are formed through three different self-complementary dimeric motifs, was obtained. The supramolecular forces involved in the stabilization of this structure are NH–O, CH–O, CH–N, CH–π, π–π, CH–Cl and unconventional N–O interactions.
- Published
- 2014
26. Synthesis, X-ray molecular structure, biological evaluation and molecular docking studies of some N
- Author
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Humayun, Pervez, Nazia, Khan, Sumera, Zaib, Muhammad, Yaqub, Muhammad Moazzam, Naseer, Muhammad Nawaz, Tahir, and Jamshed, Iqbal
- Subjects
Isatin ,Models, Molecular ,Thiosemicarbazones ,Canavalia ,Structure-Activity Relationship ,Dose-Response Relationship, Drug ,Molecular Structure ,Animals ,Artemia ,Enzyme Inhibitors ,Crystallography, X-Ray ,Urease - Abstract
A series of fifteen N
- Published
- 2016
27. Synthesis and biological evaluation of some N 4-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones
- Author
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Muhammad Yaqub, Humayun Pervez, Khalid Mohammed Khan, Mohammad S. Iqbal, and Naveeda Saira
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chemistry.chemical_classification ,Antifungal ,Urease ,biology ,Stereochemistry ,medicine.drug_class ,Aryl ,Organic Chemistry ,Brine shrimp ,biology.organism_classification ,chemistry.chemical_compound ,Enzyme ,chemistry ,biology.protein ,medicine ,Bioassay ,Phytotoxicity ,General Pharmacology, Toxicology and Pharmaceutics ,Cytotoxicity ,Nuclear chemistry - Abstract
A series of N 4-aryl-substituted 5-fluoroisatin-3-thiosemicarbazones 3a–3l was synthesized and evaluated for selected biological activities. The brine shrimp lethality bioassay was carried out to study their in vitro cytotoxicity potential and besides, their antifungal, phytotoxic and urease inhibitory effects were also investigated. Seven compounds i.e. 3a, 3d, 3f, 3g, 3h, 3j and 3k proved to be active in the brine shrimp assay, displaying promising cytotoxicity (LD50 = 6.89 × 10−5–2.79 × 10−4 M). Amongst these, 3a and 3h were found to be the most active ones (LD50 = 6.89 × 10−5 and 9.79 × 10−5 M, respectively). Compounds 3i, 3j and 3 k displayed moderate (40 %) antifungal activity against one or two fungal strains i.e. A. flavus and/or M. canis. In phytotoxicity assay, all the synthesized compounds, including the reference point 2m showed weak-to-moderate (15–70 %) activity at the highest tested concentration (500 μg/mL). In urease inhibition assay, compounds 3f, 3g and 3j proved to be the most potent inhibitors, demonstrating relatively a higher degree of enzymatic inhibition with IC50 values ranging from 37.7 to 47.3 μM.
- Published
- 2013
28. Regioselective, Catalyst-Free, One-Step Synthesis of ABCD-Fused Heterocyclic Ring System, Closely Related to Circumdatin Alkaloids
- Author
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Ruqayia Perveen, Muhammad Yaqub, Muhammad Tahir, Zahid Shafiq, and Humayun Pervez
- Subjects
Circumdatin E ,chemistry.chemical_compound ,Cascade reaction ,Chemistry ,Organic Chemistry ,Regioselectivity ,Ketene ,One-Step ,Ring (chemistry) ,Combinatorial chemistry ,Catalysis - Abstract
A novel method for the synthesis of tetracyclic fused-ring heterocycles, closely related to circumdatin alkaloids, is developed via regioselective reaction of heterocyclic ketene aminals (HKA) with 3-formylchromones.
- Published
- 2012
29. Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones
- Author
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Naveeda Saira, Humayun Pervez, Muhammad Yaqub, Mohammad S. Iqbal, and Khalid Mohammed Khan
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Substituent ,Pharmaceutical Science ,Brine shrimp ,isatin ,Article ,Analytical Chemistry ,lcsh:QD241-441 ,Acetic acid ,chemistry.chemical_compound ,lcsh:Organic chemistry ,Toxicity Tests ,Drug Discovery ,5-trifluoromethoxyisatin ,thiosemicarbazones ,5-trifluoromethoxyisatin-3-thiosemicarbazones ,toxicity ,Animals ,Moiety ,Organic chemistry ,Bioassay ,Physical and Theoretical Chemistry ,biology ,Chemistry ,Isatin ,Aryl ,Organic Chemistry ,biology.organism_classification ,Chemistry (miscellaneous) ,Toxicity ,Molecular Medicine ,Biological Assay ,Artemia ,Nuclear chemistry - Abstract
A series of twenty one N4-aryl substituted 5-trifluoromethoxyisatin-3-thiosemicarbazones 3a-3u was synthesized by the reaction of trifluoromethoxyisatin 1 with different arylthiosemicarbazides 2 in aqueous ethanol (50%), containing a few drops of acetic acid. Their structures were established on the basis of analytical (CHN) and spectral (IR, 1H-NMR, EIMS) data. All the synthesized compounds were evaluated for their toxicity potential by a brine shrimp lethality bioassay. Ten compounds i.e., 3a, 3e, 3i-3l and 3n-3q proved to be active in this assay, displaying promising toxicity (LD50 = 1.11 × 10−5 M − 1.80 × 10−4 M). Amongst these, 3k, 3n and 3o were found to be the most active ones (LD50 = 1.11 × 10−5 M − 1.43 × 10−5 M). Compound 3k showed the highest activity with a LD50 value of 1.11 × 10−5 M and can, therefore, be used as a lead for further studies. Structure-activity relationship (SAR) studies revealed that the presence of strong inductively electron-attracting trifluoromethoxy substituent at position-5 of the isatin moiety played an important role in inducing or enhancing toxic potentiality of some of the synthesized compounds.
- Published
- 2011
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30. Synthesis and biological evaluation of some N4-substituted 5-nitroisatin-3-thiosemicarbazones
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Muhammad Yaqub, Khalid Mohammed Khan, Humayun Pervez, Faiz-ul-Hassan Nasim, and Nazia Manzoor
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Antifungal ,Urease ,biology ,Chemistry ,medicine.drug_class ,Stereochemistry ,Organic Chemistry ,Brine shrimp ,biology.organism_classification ,biology.protein ,Ic50 values ,medicine ,Bioassay ,Phytotoxicity ,General Pharmacology, Toxicology and Pharmaceutics ,Cytotoxicity ,Nuclear chemistry ,Biological evaluation - Abstract
A series of 5-nitroisatin-3-thiosemicarbazones 2a–2l was synthesised and evaluated for selected biological activities. The brine shrimp lethality bioassay was carried out to study their in vitro cytotoxicity potential and besides, their antifungal, phytotoxic and urease inhibitory effects were also investigated. Only compound 2j proved to be active in the brine shrimp assay exhibiting LD50 value 1.16 × 10−3 M. Compounds 2a and 2d displayed moderate antifungal activity (50 and 40%, respectively) against M. canis. Similarly, compound 2l exhibited moderate activity (40%) against the fungal strain, A.flavus. In phytotoxicity assay, all the synthesised compounds including the reference point 2m showed weak to moderate (20–60%) activity at the highest tested concentrations (1,000 μg and 500 μg/ml, respectively). In urease inhibition assay, compounds 2a, 2i and 2k proved to be potent inhibitors demonstrating pronounced inhibition with IC50 values 0.440, 0.901 and 27.880 μM, respectively. These compounds may act as leads for further studies.
- Published
- 2011
31. Synthesis, Cytotoxic and Phytotoxic Effects of Some New N4-Aryl Substituted Isatin-3-thiosemicarbazones
- Author
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Humayun Pervez, Muhammad Yaqub, Khalid Mohammed Khan, and Muhammad Ramzan
- Subjects
chemistry.chemical_compound ,chemistry ,Isatin ,Aryl ,Drug Discovery ,Pharmaceutical Science ,Molecular Medicine ,Cytotoxic T cell ,Combinatorial chemistry - Published
- 2011
32. Synthesis and Urease Inhibitory Properties of Some New N4-Substituted 5-Nitroisatin-3-thiosemicarbazones
- Author
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M. Iqbal Choudhary, Humayun Pervez, Khalid Mohammed Khan, Muhammad Yaqub, Ajmal Khan, Nazia Manzoor, and Faiz-ul-Hassan Nasim
- Subjects
chemistry.chemical_classification ,Urease ,biology ,Stereochemistry ,Isatin ,Aryl ,Pharmaceutical Science ,chemistry.chemical_compound ,Enzyme ,chemistry ,Drug Discovery ,biology.protein ,Nitro ,Molecular Medicine ,Moiety ,IC50 ,Semicarbazone - Abstract
4 -substituted 5-nitroisatin-3-thiosemicarbazones 2a-2q has been synthesized and screened for in vitro urease inhibitory activities. Compounds 2a-2d, 2g, 2i, 2j and 2q were found to be potent inhibitors of the enzyme. Of these, 2c exhibited a potent inhibitory activity with IC50 value 16.4 � M and may act as a lead molecule for further studies. Structure-activity relationship studies revealed that electronic effects of the substituents play an important role in the urease inhibitory potential of the synthetic compounds. ery program (15-21), we have recently synthesized a number of N 4 - substituted isatin-3-thiosemicarbazones as urease inhibitors with non toxic nature (22, 23). These findings form a solid basis for further research on such compounds to develop more potent, safe and useful urease inhibitors. Furthermore, structure-activity rela- tionship (SAR) studies revealed that the type and position of the substituents on phenyl ring, substituted at N 4 of the thiosemicarba- zone moiety, play an important role in the urease inhibitory poten- tial of these compounds. To further enhance the activity of new antiurease compounds, the study of the combination of substitution at position-5 of the isatin scaffold with attachment of different aryl groups (having one or two substituents about the phenyl ring) at N 4 of the thiosemicarbazone moiety was considered worth pursuing. The present work therefore deals with the synthesis and evaluation of urease inhibitory potential of a series of seventeen N 4 - arylsubstituted 5-nitroisatin-3-thiosemicarbazones. We describe here the effects of the nature of aryl groups at N 4 (modified by placement of one or two substituents about the phenyl ring) and the presence of nitro function at position-5 of the isatin scaffold on the urease inhibitory potential of these compounds.
- Published
- 2010
33. Synthesis and biological evaluation of some new N4-substituted isatin-3-thiosemicarbazones
- Author
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Muhammad Ramzan, Khalid Mohammed Khan, Faiz-ul-Hassan Nasim, Humayun Pervez, and Zahid H. Chohan
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Isatin ,Thiosemicarbazones ,Urease ,Stereochemistry ,Brine shrimp ,Inhibitory Concentration 50 ,chemistry.chemical_compound ,Drug Discovery ,Animals ,Bioassay ,Enzyme Inhibitors ,IC50 ,Pharmacology ,chemistry.chemical_classification ,Dose-Response Relationship, Drug ,biology ,Chemistry ,General Medicine ,biology.organism_classification ,In vitro ,Enzyme ,biology.protein ,Phytotoxicity ,Artemia ,Drug Screening Assays, Antitumor ,Nuclear chemistry - Abstract
A new series of 12 N(4)-substituted isatin-3-thiosemicarbazones 2a-l has been synthesized, characterized and screened for in vitro cytotoxic, phytotoxic and urease inhibitory effects. All the compounds proved to be active in the brine shrimp bioassay; 2a, 2b, 2d, 2f and 2h-l exhibited a high degree of cytotoxic activity (LD(50) = 1.10 x 10(- 5) M-3.10 x 10(- 5) M). In urease-inhibition assay, compounds 2a, 2b, 2e, 2f, 2h-j and 2l proved to be potent inhibitors displaying relatively much greater inhibition of the enzyme with IC(50) values ranging from 20.6 microM to 50.6 microM. Amongst these, 2a and 2f were found to be the most potent ones exhibiting pronounced inhibition with IC(50) value 20.6 microM. All the synthetic compounds showed weak to moderate (10-40%) phytotoxicity at the highest tested concentration (500 microg/mL) indicating their usefulness as inhibitors of soil ureases.
- Published
- 2008
34. Pharmacokinetic Study of Copper (II) Acetylsalicylate
- Author
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Humayun Pervez, Muhammad Sher, Maryiam Saeed, and Mohammad S. Iqbal
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Adult ,Male ,Biodistribution ,Adolescent ,Endocrinology, Diabetes and Metabolism ,Clinical Biochemistry ,Administration, Oral ,Pharmacology ,Biochemistry ,Inorganic Chemistry ,Young Adult ,chemistry.chemical_compound ,Pharmacokinetics ,Oral administration ,Organometallic Compounds ,medicine ,Humans ,Chromatography, High Pressure Liquid ,Volume of distribution ,Aspirin ,Biochemistry (medical) ,General Medicine ,Salicylates ,Copper aspirinate ,Copper salicylate ,chemistry ,Female ,Salicylic acid ,medicine.drug - Abstract
This study was aimed at determination of pharmacokinetic parameters of copper (II) acetylsalicylate (CAS). Ten volunteers received a 60-mg dose of CAS. Blood samples were collected just before and after 0.25, 0.5, 0.75, 1.0, 1.5, 2.5, 3.0, 3.5, 4.0, 4.5, 5.5, 7.0, 10, and 12.0 h of administration of the drug. The plasma samples were analyzed for CAS and its metabolites by a validated high-performance liquid chromatography method having a suitable lower limit of quantification. The dose of 60 mg was well tolerated without any adverse effect. The maximum plasma concentration of CAS was found to be 0.38 mg L(-1) with t (max) of 0.72 h. The plasma half-life, clearance, and volume of distribution of CAS were 8.67 h, 66.30 L h(-1) and 829 L kg(-1), respectively. The elimination of CAS, acetylsalicylic acid, copper salicylate, and salicylic acid follows the first order kinetics with r (2) 0.979, 0.880, 0.991, and 0.998, respectively. The study provided for the first time the pharmacokinetic data for CAS after oral administration of CAS. The data were found to be useful in understanding the claimed enhanced anti-inflammatory activity of the drug as compared with that of acetylsalicylic acid.
- Published
- 2008
35. ChemInform Abstract: Synthesis of Hexacyclic Fused Isocoumarin Framework Through Selective Domino Multicyclizations under Catalyst and Solvent Free Conditions
- Author
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Humayun Pervez, Nasim Hasan Rama, Tariq Mahmood Babar, Muhammad Moazzam Naseer, Muhammad Rauf, and Masahiro Ebihara
- Subjects
Solvent free ,General Medicine ,Chloride ,Domino ,Catalysis ,Stereocenter ,Isocoumarin ,chemistry.chemical_compound ,chemistry ,Organic reaction ,Yield (chemistry) ,medicine ,Organic chemistry ,medicine.drug - Abstract
A novel fused isocoumarin skeleton has been synthesized through selective domino multicyclizations by mixing homothallic acid and 2,3-diphenylacryloyl chloride at 200 °C under catalyst and solvent free reaction conditions. Six fused rings with two stereogenic centers were assembled in a convenient one-pot operation in good yield. The resulting hexacyclic fused isocoumarin skeleton and its stereochemistry was fully characterized and unambiguously confirmed by X-ray diffraction analysis.
- Published
- 2015
36. Synthesis and fluorine-mediated interactions in methanol-encapsulated solid state self-assembly of an isatin-thiazoline hybrid
- Author
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Maqbool Ahmad, Loïc Toupet, Muhammad Moazzam Naseer, Taibi Ben Hadda, Humayun Pervez, Bahauddin Zakariya University (BZU), Faculté des sciences [Oujda], Université Mohammed Premier [Oujda], Institut de Physique de Rennes (IPR), Université de Rennes (UR)-Centre National de la Recherche Scientifique (CNRS), Département de chimie, Quaid-i-Azam University Islamabad, We acknowledge partial funding of this research work and the award of indigenous PhD scholarship to MA by Higher Education Commission (HEC), Government of Pakistan., Université de Rennes 1 (UR1), and Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS)
- Subjects
[PHYS]Physics [physics] ,fluorine-mediated interactions ,synthesis ,Stereochemistry ,Isatin ,Thiazoline ,Organic Chemistry ,Supramolecular chemistry ,self-assembly ,Analytical Chemistry ,Inorganic Chemistry ,chemistry.chemical_compound ,Crystallography ,chemistry ,Bromide ,Yield (chemistry) ,isatin-thiazoline hybrid ,[PHYS.COND.CM-MS]Physics [physics]/Condensed Matter [cond-mat]/Materials Science [cond-mat.mtrl-sci] ,Molecule ,Methanol ,Self-assembly ,Spectroscopy ,layered structure - Abstract
International audience; An exciting isatin-thiazoline hybrid molecule 2 having -C=N-N=C- linkage has been synthesized in 88% yield by the reaction of 5-fluoroisatin with N-(4-fluorophenyl)hydrazinecarbothioamide followed by condensation of the resultant isatin-thiosemicarbazone intermediate with p-chlorophenacyl bromide. The solid state self-assembly of this hybrid molecule was studied by X-ray crystallographic technique. A layered assembly composed of 1D-chains with methanol molecules encapsulated between every two chains is obtained, making a bi-chain sandwich like structure. The supramolecular forces involved in the stabilization of this structure are importantly fluorine-mediated interactions (C-H···F, F···S and F···π) along with others i.e. N-H···O, O-H···O, C-H···O, Cl···π, C-H···π and π···π interactions. To the best of our knowledge, this is the first example of solid state fluorine-mediated C-H···F, F···S and F···π interactions found in a family of isatin-based compounds
- Published
- 2015
37. Antibacterial cobalt (II), copper (II), nickel (II) and zinc (II) complexes of mercaptothiadiazole—derived furanyl, thienyl, pyrrolyl, salicylyl and pyridinyl Schiff bases
- Author
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Abdul Rauf, Claudiu T. Supuran, Zahid H. Chohan, Khalid Mohammed Khan, and Humayun Pervez
- Subjects
Magnetic Resonance Spectroscopy ,chemistry.chemical_element ,Microbial Sensitivity Tests ,Bacillus subtilis ,Zinc ,medicine.disease_cause ,Medicinal chemistry ,Nickel ,Metals, Heavy ,Spectroscopy, Fourier Transform Infrared ,Thiadiazoles ,Drug Discovery ,medicine ,Organic chemistry ,Pyrroles ,Sulfhydryl Compounds ,Furans ,Escherichia coli ,Schiff Bases ,Pharmacology ,biology ,Electric Conductivity ,Cobalt ,General Medicine ,Nuclear magnetic resonance spectroscopy ,biology.organism_classification ,Copper ,Anti-Bacterial Agents ,chemistry ,Spectrophotometry, Ultraviolet ,Antibacterial activity - Abstract
A series of Co (II), Cu (II), Ni (II) and Zn (II) complexes of mercaptothiadiazole-derived furanyl, thienyl, pyrrorlyl, salicylyl and pyridinyl Schiff bases were synthesized, characterized and screened for their in vitro antibacterial activity against four Gram-negative, Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi and Shigella fexneri, and two Gram-positive; Bacillus subtilis and Staphylococcus aureous bacterial strains. The results of these studies show the metal complexes to be more antibacterial as compared to the prepared un-complexed Schiff bases.
- Published
- 2006
38. Improved physicochemical characteristics of artemisinin using succinic acid
- Author
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Muhammad Tayyab, Ansari, Humayun, Pervez, Muhammad Tariq, Shehzad, Syed, Saeed-ul-Hassan, Zahid, Mehmood, Syed Nisar Hussain, Shah, Muhammad Tahir, Razi, and Ghulam, Murtaza
- Subjects
Calorimetry, Differential Scanning ,Chemistry, Pharmaceutical ,Succinic Acid ,Crystallography, X-Ray ,Artemisinins ,Diffusion ,Excipients ,Antimalarials ,Kinetics ,Freeze Drying ,Models, Chemical ,Solubility ,Spectroscopy, Fourier Transform Infrared ,Solvents ,Technology, Pharmaceutical ,Transition Temperature - Abstract
Artemisinin (ARMN) is a potent antimalarial drug, which is effective against multidrug resistant strains of Plasmodium falciparum and produces rapid recovery even in patients with cerebral malaria. Being poorly soluble in water, artemisinin is incompletely absorbed after oral intake due to poor dissolution characteristics in the intestinal fluids. To enhance these properties, solid dispersions of artemisinin with succinic acid (SUC) were prepared using drug-carrier ratios 1 : 1, 1 : 4, 1 : 6, 1 : 8 and 1 : 10 by solvent evaporation and freeze drying methods. These solid dispersions were characterized by differential scanning calorimetery (DSC), Fourier transform infrared spectroscopy (FTIR), x-ray diffraction patterns (XRD), phase solubility and dissolution kinetics evaluated by applying zero order, first order, Higuchi, and Korsmeyer-Peppas models. Physical mixtures produced significantly higher aqueous solubility and rate of dissolution as compared to artemisinin alone. The dissolution profiles of all formulations followed Higuchi model and exhibited diffusion-controlled release of drug. Solvent evaporation method (SLVPs) exhibited improved solubility and freeze dried solid dispersions (FDSDs) produced highest solubility but stability constant was opposite. ARMN and SUC both were found completely crystalline as shown by their XRD patterns. Physical mixtures (PMs) showed reduced intensity in their XRD patterns while solid dispersions by SLVPs exhibited twice reduced intensity and much displaced angles, whereas FDSDs showed synergistic effects in some of ARMN and SUC peaks. DSC thermograms of FDSDs at drug-carrier ratios 1 : 1-1 : 4 showed lower melting temperature and enthalpy change (deltaH) values than respective SLVPs, whereas at higher ratios, a reverse was true. SLVPs showed displaced methyl stretching bands at lower drug-carrier ratios and exhibited O-H stretching characteristic bands of SUC at higher drug-carrier ratios. In addition, carbonyl group and C-O stretching vibrations characteristic of SUC (1307 cm(-1)) appeared prominently compared to PMs, whereas C-O stretching characteristic bands of ARMN disappeared at higher ratios. FDSDs exhibited distinct nature of bonding compared to respective SLVPs and PMs.
- Published
- 2014
39. Organometallic-based antibacterial and antifungal compounds: transition metal complexes of 1,1′-diacetylferrocene-derived thiocarbohydrazone, carbohydrazone, thiosemicarbazone and semicarbazone
- Author
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Humayun Pervez, Khalid Mohammed Khan, Claudiu T. Supuran, and Zahid H. Chohan
- Subjects
Antifungal Agents ,Metallocenes ,Metal ions in aqueous solution ,chemistry.chemical_element ,Microbial Sensitivity Tests ,Zinc ,Carbohydrazide ,Ligands ,chemistry.chemical_compound ,Nickel ,Drug Discovery ,Organometallic Compounds ,Organic chemistry ,Ferrous Compounds ,Candida albicans ,Semicarbazone ,Pharmacology ,Thiocarbohydrazide ,Semicarbazide ,biology ,Chemistry ,Hydrazones ,Cobalt ,General Medicine ,biology.organism_classification ,Anti-Bacterial Agents ,Antibacterial activity ,Copper ,Nuclear chemistry - Abstract
Organometallic-based, 1,1'-diacetylferrocene-derived antibacterial and antifungal thiocarbohydrazone, carbohydrazone, thiosemicarbazone and semicarbazone have been prepared by condensing equimolar amount of 1,1'-diacetylferrocene with thiocarbohydrazide, carbohydrazide thiosemicarbazide and semicarbazide, respectively. These were used as ligands for the preparation of their cobalt (II), copper (II), nickel (II) and zinc (II) metal complexes. All the synthesized ligands and their complexes were characterized by IR, NMR, elemental analyses, molar conductances, magnetic moments and electronic spectral data. These synthesized compounds were screened for their antibacterial activity against Escherichia coli, Bacillus subtillis, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella typhi, and for antifungal activity against Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium solani and Candida glaberata using the agar-well diffusion method. All the compounds showed good antibacterial and antifungal activity which increased on coordination with the metal ions thus, introducing a novel class of organometallic-based antibacterial and antifungal agents.
- Published
- 2005
40. Isatin-derived Antibacterial and Antifungal Compounds and their Transition Metal Complexes
- Author
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Khalid Mohammed Khan, Claudiu T. Supuran, Abdur Rauf, Zahid H. Chohan, and Humayun Pervez
- Subjects
Isatin ,Magnetic Resonance Spectroscopy ,Spectrophotometry, Infrared ,Aspergillus flavus ,Microbial Sensitivity Tests ,Ligands ,Hydrazide ,Structure-Activity Relationship ,chemistry.chemical_compound ,Anti-Infective Agents ,Metals, Heavy ,Drug Discovery ,Organometallic Compounds ,Organic chemistry ,Thiazole ,Candida albicans ,Pharmacology ,Sulfonyl ,chemistry.chemical_classification ,Carbon Isotopes ,Bacteria ,Molecular Structure ,biology ,Electron Spin Resonance Spectroscopy ,Fungi ,General Medicine ,biology.organism_classification ,chemistry ,Benzothiazole ,Protons ,Antibacterial activity ,Nuclear chemistry - Abstract
A series of isatins incorporating thiazole, thiadiazole, benzothiazole and p-toluene sulfonyl hydrazide moieties, along with their cobalt(II), copper(II), nickel(II) and zinc(II) metal complexes have been synthesized and characterized by elemental analyses, molar conductances, magnetic moments, IR, NMR and electronic spectral data. These compounds have been screened for antibacterial activity against Escherichia coli, Bacillus subtillis, Shigella flexneri, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella typhi, and for antifungal activity against Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium solani and Candida glaberata using the agar-well diffusion method. All the synthesized compounds have shown good affinity as antibacterial and/or antifungal agents which increased in most of the cases on complexation with the metal ions.
- Published
- 2004
41. Antibacterial and Antifugal Mono- and Di-substituted Symmetrical and Unsymmetrical Triazine-derived Schiff-bases and their Transition Metal Complexes
- Author
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Ghulam M. Maharvi, Zahid H. Chohan, Khalid Mohammed Khan, Humayun Pervez, Abdur Rauf, and Claudiu T. Supuran
- Subjects
Antifungal Agents ,Magnetic Resonance Spectroscopy ,Inorganic chemistry ,Molecular Conformation ,chemistry.chemical_element ,Infrared spectroscopy ,Microbial Sensitivity Tests ,Zinc ,Metal ,chemistry.chemical_compound ,Transition metal ,Drug Discovery ,Octahedral molecular geometry ,Schiff Bases ,Pharmacology ,Molecular Structure ,Triazines ,Chemistry ,General Medicine ,Anti-Bacterial Agents ,Crystallography ,Nickel ,Salicylaldehyde ,Metals ,visual_art ,visual_art.visual_art_medium ,Cobalt - Abstract
A new series of antibacterial and antifungal triazine-derived mono- and di-substituted (symmetrical and unsymmetrical) Schiff-bases and their cobalt(II), copper(II), nickel(II) and zinc(II) metal complexes have been synthesized and characterized by their elemental analyses, molar conductances, magnetic moments and IR and electronic spectral measurements. IR spectra indicated the ligands to act as tridentate towards divalent metal ions via a trazine-N, the azomethine-N and, indole-NH and deprotonated-O of salicylaldehyde. The magnetic moments and electronic spectral data suggest octahedral geometry for the Co(II), Ni(II) and Zn(II)complexes and square-pyramid for Cu(II) complexes. NMR spectral data of the ligands and their diamagnetic zinc(II) complexes well-define their proposed structures/geometries. Elemental analyses data of the ligands and metal complexes agree with their proposed structures/geometries. The synthesized ligands, along with their metal complexes were screened for their antibacterial activity against Escherichia coli, Bacillus subtillis, Shigella flexneri, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella typhi and for antifungal activity against Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium solani and Candida glaberata. The results of these studies show the metal complexes to be more antibacterial/ antifungal against two or more species as compared to the uncomplexed Schiff-base ligands.
- Published
- 2004
42. SYNTHESIS AND CHARACTERIZATION OF ANTIBACTERIAL Co(II), Cu(II), Ni(II), AND Zn(II) COMPLEXES OF ACYLHYDRAZINE DERIVED PYRROLYL COMPOUNDS
- Author
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Humayun Pervez, Samina Kausar, Claudiu T. Supuran, and Zahid H. Chohan
- Subjects
Stereochemistry ,Metal ions in aqueous solution ,Acylhydrazine ,Carbon-13 NMR ,medicine.disease_cause ,Inorganic Chemistry ,Metal ,chemistry.chemical_compound ,Deprotonation ,chemistry ,visual_art ,Polymer chemistry ,medicine ,visual_art.visual_art_medium ,Physical and Theoretical Chemistry ,Escherichia coli - Abstract
Acylhydrazine derived pyrrolyl ligands and their metal [Co(II), Cu(II), Ni(II), and Zn(II)] complexes have been prepared and characterized on the basis of elemental analyses, magnetic moments, molar conductances and spectroscopic (electronic, IR, 1H and 13C NMR) data. All of these compounds function as tridentate ligands, with their deprotonated enolic form being preferred in the coordination to the metal ions. The title synthesized ligands and their metal(II) complexes have been screened for bactericidal activity against the pathogenic bacterial species Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa, and it is shown that the metal complexes act as more active antibacterial agents than the uncomplexed ligands from which they derive.
- Published
- 2002
43. Antibacterial Role of SO42− , NO3− , C2O42− and CH3CO2− Anions on C<scp>u</scp>(II) and Z<scp>n</scp>(II) Complexes of a Thiadiazole-derived Pyrrolyl Schiff Base
- Author
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Claudiu T. Supuran, Humayun Pervez, Zahid H. Chohan, and Abdul Rauf
- Subjects
Pharmacology ,Schiff base ,Chemistry ,Nanotechnology ,Toxicology ,Condensation reaction ,medicine.disease_cause ,Medicinal chemistry ,Inorganic Chemistry ,Metal ,chemistry.chemical_compound ,visual_art ,Drug Discovery ,visual_art.visual_art_medium ,medicine ,Chelation ,Escherichia coli ,Stoichiometry - Abstract
A condensation reaction of 2-amino-1,3,4-thiadiazole with 2-pyrrolecarboxaldehyde to form tridentate NNN donor Schiff base has been performed. The prepared Schiff base was further used for the formation of metal complexes having stoichiometry [M(L)2]Xn , where M=Cu(II) or Zn(II), L=N-(2-pyrrolylmethylene)-2-amino-1,3,4-thiadiazole, X=SO42− , NO3− , C2O42− or CH3CO2− and n=1 or 2. The new compounds described here have been characterized by their physical, spectral and analytical data, and have been screened against several bacterial strains such as Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa. The antibacterial potency of the Schiff base increased upon chelation/complexation, having the same metal ion (cation) but different anions opening up a novel approach in finding new ways to fight against antibiotic resistant strains.
- Published
- 2002
44. Antibacterial Co(II), Cu(II), Ni(II) and Zn(II) Complexes of Thiadiazole Derived Furanyl, Thiophenyl and Pyrrolyl Schiff Bases
- Author
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Abdul Rauf, Andrea Scozzafava, Zahid H. Chohan, Humayun Pervez, and Claudiu T. Supuran
- Subjects
Staphylococcus aureus ,Stereochemistry ,chemistry.chemical_element ,Microbial Sensitivity Tests ,Zinc ,Medicinal chemistry ,chemistry.chemical_compound ,Thiadiazoles ,Nickel ,Drug Discovery ,Escherichia coli ,Thiophene ,Molecule ,Pyrroles ,Chelation ,Furans ,Schiff Bases ,Pharmacology ,Molecular Structure ,Cobalt ,General Medicine ,Condensation reaction ,Anti-Bacterial Agents ,chemistry ,Pseudomonas aeruginosa ,Antibacterial activity ,Copper - Abstract
2-Amino-1,3,4-thiadiazole undergoes a condensation reaction with furane-, thiophene- and pyrrole-2-carboxaldehyde to form tridentate NNO, NNS and NNN donor Schiff bases. These Schiff bases were further used to obtain complexes of the type [M(L)2]X, where M = Co(II), Cu(II), Ni(II) or Zn(II), L = L1, L2 or L3 and X = Cl2. The new compounds described here have been characterized by their physical, spectral and analytical data, and have been screened for antibacterial activity against several bacterial strains such as Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa. The antibacterial potency of the Schiff bases increased upon chelation/complexation in comparison to the uncomplexed Schiff bases against the tested bacterial species thus, opening new approaches to find new ways in the fight against antibiotic-resistant strains.
- Published
- 2002
45. 5-Nitroisatin-derived thiosemicarbazones: potential antileishmanial agents
- Author
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Nazia Manzoor, Khalid Mohammed Khan, Humayun Pervez, and Muhammad Yaqub
- Subjects
Pharmacology ,Isatin ,Thiosemicarbazones ,Dose-Response Relationship, Drug ,Molecular Structure ,General Medicine ,Trypanocidal Agents ,chemistry.chemical_compound ,Structure-Activity Relationship ,chemistry ,Parasitic Sensitivity Tests ,Drug Discovery ,medicine ,Ic50 values ,Organic chemistry ,Pentamidine ,medicine.drug ,Trypanocidal agent ,Leishmania major - Abstract
A series of 29 previously reported N(4)-substituted 5-nitroisatin-3-thiosemicarbazones 2-30 has been screened for leishmanicidal potential. Compounds 2-4, 7, 8, 10-13, 15-19, 21, 23, 24, 26, 28 and 30 exhibited good to excellent antileishmanial activities with IC50 values ranging from 0.44 ± 0.02 to 32.38 ± 0.66 µg/mL. Of these, 5, 7, 19 and 28 proved to be the most active antileishmanial agents, displaying activities with IC50 values 1.78 ± 0.35, 0.44 ± 0.02, 1.91 ± 0.04 and 4.28 ± 0.75 µg/mL, respectively, which were even better than the standard drug, pentamidine (IC50 = 5.09 ± 0.04 µg/mL). This study presents the first example of exhibition of leishmanicidal potential by isatin-thiosemicarbazones and as such furnishes a solid basis for further research on these compounds to develop more potent antileishmanial agents.
- Published
- 2013
46. ChemInform Abstract: Regioselective, Catalyst-Free, One-Step Synthesis of ABCD-Fused Heterocyclic Ring System, Closely Related to Circumdatin Alkaloids
- Author
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Muhammad Tahir, Ruqayia Perveen, Humayun Pervez, Muhammad Yaqub, and Zahid Shafiq
- Subjects
chemistry.chemical_compound ,chemistry ,Stereochemistry ,Regioselectivity ,Ketene ,One-Step ,General Medicine ,Ring (chemistry) ,Catalysis - Abstract
A simple protocol is developed for the reaction of heterocyclic ketene aminals with 3-formylchromones to give tetracyclic heterocycles.
- Published
- 2012
47. Improved physicochemical characteristics of artemisinin-nicotinamide solid dispersions by solvent evaporation and freeze dried methods
- Author
-
Muhammad Tayyab, Ansari, Humayun, Pervez, Muhammad Tariq, Shehzad, Zahid, Mahmood, Muhammad Tahir, Razi, Nazar Muhammad, Ranjha, and Nuzhat, Khanum
- Subjects
Niacinamide ,Antimalarials ,Freeze Drying ,Calorimetry, Differential Scanning ,Solubility ,X-Ray Diffraction ,Spectroscopy, Fourier Transform Infrared ,Volatilization ,Artemisinins - Abstract
Artemisinin (ARMN) is a drug of choice against drug-resistant malaria especially due to Plasmodium falciparum. Being poorly soluble in water, its solid dispersions with nicotinamide (NA) were prepared at various drug-carrier ratios (1:1, 1:4, 1:6, 1:8, 1:10) by solvent evaporation and freeze drying methods. These solid dispersions were characterized by differential scanning calorimetery (DSC), fourier transform infrared spectroscopy (FTIR), X-ray diffraction patterns (XRD), phase solubility and dissolution studies. Artemisinin and nicotinamide both were found completely crystalline as shown by their XRD patterns. Physical mixtures (PMs) showed decreased intensity in their XRD patterns while solid dispersions by solvent evaporation method (SLVPs) exhibited displaced angles and decreased intensity whereas freeze dried solid dispersions (FDSDs) showed least number of peaks having low intensity and maximum displaced angles. DSC thermograms of drug-carrier ratios at 1:1-1:4 showed lower melting temperature than artemisinin and nicotinamide in all preparations. Endothermic temperature of artemisinin in PMs and SLVPs increased with rise of nicotinamide content upto 1:6 ratio followed by decline. All samples showed crystallization temperature below the artemisinin except drug-carrier ratio 1:6 of PMs while δH value was minimum at this ratio. FDSDs produced lowest endothermic temperature than corresponding PMs and SLVPs. SLVPs exhibited band shifting in both functional and fingerprint region compared to respective PMs as exhibited by their FTIR spectra. FDSDs and SLVPs showed different nature of bonding among artemisinin and nicotinamide. FDSDs produced strongest CONH(2) bonding followed by SLVPs and PMs respectively. PMs produced significantly higher aqueous solubility and rate of dissolution as compared to artemisinin alone. SLVPs exhibited improved solubility and dissolution profile corresponding to PMs. FDSDs showed highest release rate and aqueous solubility followed by SLVPs and PMs at all ratios. PMs and SLVPs showed their highest dissolution profile at 1:6 drug-carrier ratio followed by gradual decrease while FDSDs progressed in dissolution rate with increase of nicotinamide content successively upto maximum at 1:10 ratio.
- Published
- 2012
48. Synthesis and biological evaluation of some new N4-aryl substituted 5-chloroisatin-3-thiosemicarbazones
- Author
-
Faiz-ul-Hassan Nasim, Muhammad Yaqub, Muhammad Ramzan, Humayun Pervez, and Khalid Mohammed Khan
- Subjects
Isatin ,Thiosemicarbazones ,Urease ,Stereochemistry ,Medicinal chemistry ,chemistry.chemical_compound ,Structure-Activity Relationship ,Drug Discovery ,Bioassay ,Moiety ,Animals ,Araceae ,Enzyme Inhibitors ,Cytotoxicity ,Semicarbazone ,chemistry.chemical_classification ,biology ,Dose-Response Relationship, Drug ,Molecular Structure ,Aryl ,Stereoisomerism ,Enzyme ,chemistry ,biology.protein ,Phytotoxicity ,Artemia - Abstract
A new series of sixteen N4-aryl substituted 5-chloroisatin-3-thiosemicarbazones 2a-2p has been synthesized, characterized and tested for selected biological activities i.e. cytotoxicity, phytotoxicity and urease inhibition. In the brine shrimp bioassay, all the synthesized compounds gave LD50 values >2.30 X 10-4 M - 2.79 X 10-4 M and were, therefore, found to be almost inactive, whereas in phytotoxicity assay, regardless of the nature of aryl substituents, they displayed weak to moderate (5-40%) phytotoxic activity at the highest tested concentrations (500 or 1000 μg/mL). In urease inhibition bioassay, compounds 2a, 2c, 2e, 2f, 2k and 2m exhibited relatively a higher degree of urease inhibition with IC50 values ranging from 38.91 μM to 76.65 μM and thus proved to be potent inhibitors of the enzyme. Of these, 2f and 2m displayed pronounced inhibition with IC50 values 38.91 μM and 39.50 μM, respectively, and may act as lead compounds for further studies. Structure-activity relationship (SAR) studies revealed that electronic effects of the substituents about the phenyl ring at N4 of the thiosemicarbazone moiety played an important role in enhancing the urease inhibitory potential of some of the synthesized compounds.
- Published
- 2011
49. Studies on Biologically Active Complexes of Nickel(II), Copper(II) and Zinc(II) with Tridentate NNO, NNS and NNN Donor Pyrazine Derived Ligands
- Author
-
Zahid H. Chohan and Humayun Pervez
- Subjects
Schiff base ,Pyrazine ,Inorganic chemistry ,chemistry.chemical_element ,Biological activity ,Zinc ,Copper ,Inorganic Chemistry ,Metal ,chemistry.chemical_compound ,Nickel ,chemistry ,visual_art ,Polymer chemistry ,visual_art.visual_art_medium ,Physical and Theoretical Chemistry ,Antibacterial activity - Abstract
New biologically active tridentate pyrazine-derived NNO, NNS and NNN Schiff base ligands (I, II and III) and their nickel(II), copper(II) and zinc(II) complexes 1–9. have been synthesised and characterised on the basis of conductance and magnetic measurements, elemental analyses, and 1H-NMR, IR and electronic-spectral data. The synthesised ligands and their complexes have been evaluated for antibacterial activity against Esoherichi a colt- Pseudomonas aeruginosa and Klebsiella pneumoniae The activity data show the metal complexes to be more antibacterial than the ligands against one or more bacterial species.
- Published
- 1993
50. 1-[2-Oxo-5-(trifluoromethoxy)indolin-3-ylidene]-4-[4-(trifluoromethyl)phenyl]thiosemicarbazide
- Author
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Mohammad S. Iqbal, Naveeda Saira, M. Nawaz Tahir, Humayun Pervez, and Muhammad Yaqub
- Subjects
Semicarbazide ,Crystallography ,Chemistry ,Hydrogen bond ,Substituent ,Thio ,General Chemistry ,Dihedral angle ,Condensed Matter Physics ,Ring (chemistry) ,Organic Papers ,Medicinal chemistry ,chemistry.chemical_compound ,QD901-999 ,General Materials Science ,Benzene - Abstract
In the title compound, C17H10F6N4O2S, an intramolecular N—H...N hydrogen bonds forms an S(5) ring whereas N—H...O and C—H...S interactions complete S(6) ring motifs. The dihedral angle between the fused ring system and the phenyl ring is 6.68 (8)°. In the crystal, the molecules are dimerized due to N—H...O interactions. π–π interactions are present between the benzene rings [centroid–centroid distance = 3.6913 (15) Å] and between the five membered ring and the trifluoromethyl)phenyl ring [centroids–centroid distance = 3.7827 (16) Å]. One of the trifluoromethoxy F atoms is disordered over two sites with occupancy ratio of 0.76 (3):0.24 (3). The F atoms of the p-trifluoromethyl substituent are disordered over three sets of sites with an occupancy ratio of 0.70 (2):0.152 (11):0.147 (13).
- Published
- 2010
Catalog
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