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Hydrazine and its derivatives have served as a conventional bipropellant fuel for several decades. However, their extremely acute toxicity and carcinogenicity, high volatility, and environmental impact have attracted significant attention. In order to synthesize green bipropellant fuels with high density, high specific impulse, and good thermal stability, three novel N -alkyl-1,2,4-triazole–borane complexes were successfully synthesized by reacting alkylated 1,2,4-triazole coordinated with sodium borohydride in the presence of ammonium sulfate. During the droplet test with white fuming nitric acid, there was a relatively short ignition delay time of 98 ms. Additionally, these hypergolic fuels possessed a high density exceeding 1.10 g cm–3 , and the specific impulse is ranging from 187 to 199 s, and the highest decomposition temperature reaches 153.4 °C. These results demonstrate their great potential as hypergolic fuels or hypergolic ionic liquid additives in the field of hypergolic materials. [ABSTRACT FROM AUTHOR]

Hormone receptor (HR)-positive breast cancer represents tumours that express estrogen and/or progesterone enzymes, which play a crucial role in the growth and proliferation of breast cancer cells. Aromatase inhibitors (AIs) are drugs that inhibit the enzyme aromatase, involved in the biosynthesis of estrogen and are used for the treatment of HR-positive breast cancer. The USFDA-approved nonsteroidal AIs contain 1,2,4-triazole heterocycle. So, in the present study, we screened seventy-eight 1,2,4-triazole analogues from different literature resources and generated a pharmacophore model. After several validation protocols, Hypo1 was selected as the best model and was used as a 3D query for screening 1,2,4-triazole analogues (15,583) obtained from the CHEMBL database. A dataset containing 320 ligands with estimated activity (IC50< 0.1 µM) was subjected to molecular docking against the aromatase enzyme (PDB ID: 3S79). Amongst the 320 ligands, 30 compounds exhibited better binding energy compared to the standard drug letrozole. These 30 hits were further considered for the design of two novel molecules which were initially assessed for their ADMET properties followed by pharmacophore mapping, docking and molecular dynamics simulation. The in silico findings suggest that both the designed molecules can be considered drug-like candidates for the treatment of breast cancer through aromatase inhibition. [ABSTRACT FROM AUTHOR]

A series of chelating N N proligands, 3‐(2‐pyridyl)‐5‐alkyl‐1,2,4‐triazoles (HLAlk), where alkyl=methyl, ethyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl was used as building blocks for designing of coordination compounds. Their reaction with an equimolar amount of [PdCl2(CH3CN)2] led to formation of series of six novel palladium complexes [Pd(HLAlk)Cl2], in which ligands are coordinated in the acid form. New proligands and Pd(II) complexes were characterized by IR, 1H and 13C NMR spectroscopy and elemental analysis. The Pd(II) complexes showed an unusual downfield shift in 1H NMR of the aliphatic proton that is the closest to triazole ring, which suggests the C−H...Cl hydrogen bonding, supported by X‐ray data for Pd(HLc−Pr)Cl2 and Pd(HLc−Bu)Cl2. [ABSTRACT FROM AUTHOR]

The title compound, bis[μ-2,2′-(4H-1,2,4-triazole-3,5-diyl)diacetato]bis[diaquacopper(II)] dihydrate, [Cu2(C6H5N3O4)2(H2O)4]·2H2O, is a dinuclear octahedral CuII triazole-based complex. The central copper atoms are hexa-coordinated by two nitrogen atoms in the equatorial positions, two equatorial oxygen atoms of two carboxylate substituents in position 3 and 5 of the 1,2,4-triazole ring, and two axial oxygen atoms of two water molecules. Two additional solvent water molecules are linked to the title molecule by O—H⋯N and O⋯H—O hydrogen bonds. The crystal structure is built up from the parallel packing of discrete supramolecular chains running along the a-axis direction. Hirshfeld surface analysis suggests that the most important contributions to the surface contacts are from H⋯O/O⋯H (53.5%), H⋯H (28.1%), O⋯O (6.3%) and H⋯C/C⋯H (6.2%) interactions. The crystal studied was twinned by a twofold rotation around [100]. [ABSTRACT FROM AUTHOR]

This study presents the synthesis, characterization and Hirshfeld surface analysis of the title mononuclear complex, [PdCl2(C12H14N4)]·C3H7NO. The compound crystalizes in the P21/c space group of the monoclinic system. The asymmetric unit contains one neutral complex Pd(HLc-Pe)Cl2 [HLc-Pe is 2-(3-cyclopentyl-1,2,4-triazol-5-yl)pyridine] and one molecule of DMF as a solvate. The Pd atom has a square-planar coordination. In the crystal, molecules are linked by intermolecular N—H⋯O and C—H⋯N hydrogen bonds, forming layers parallel to the bc plane. A Hirshfeld surface analysis showed that the H⋯H contacts dominate the crystal packing with a contribution of 41.4%. The contribution of the N⋯H/H⋯N and H⋯O/O⋯H interactions is somewhat smaller, amounting to 12.4% and 5%, respectively. [ABSTRACT FROM AUTHOR]

Due to chronic inflammation, elevated cyclooxygenase (COX-2) level leads to tumorigenesis, proliferation, invasion, angiogenesis and metastasis. Therefore, suppression of COX-2 enzyme is a fascinating approach in cancer treatment. In the present study, natural product eugenol was modified to develop new 1,2,4-triazole derivatives as antiCOX-2 and antiproliferative agents. The structures of newly prepared derivatives were established using sophisticated analytical techniques. The antiproliferative result showed compound 10 to be equipotent to doxorubicin towards MDA-MB 231 and PC-3 cancer cells with IC50 1.42 and 5.69 μM, respectively and potent COX-2 inhibitor with IC50 0.28 μM. Compound 10 was also non carcinogenic, non mutagenic with good drug likeness property as depicted by in silico physicochemical and pharmacokinetic studies. The docking results against COX-2 protein showed highest binding energy for compound 10 which was found to be in consistent with the cytoxicity and COX-2 results. In conclusion, compound 10 could harness COX-2 and cell proliferation and could be a promising candidate in cancer therapy. [ABSTRACT FROM AUTHOR]

The article is devoted to the polypharmacological profiling of 4-((5-(decylthio)-4-methyl4H-1,2,4-triazole-3-yl)methyl)morpholine, which has potential as an antimicrobial agent. The study was conducted using 15,148 electronic pharmacophore models of organisms, ranked according to the Tversky index. A detailed analysis of the compound’s interactions with selected enzymes showed that 4-((5-(decylthio)-4-methyl-4H-1,2,4-triazole-3- yl)methyl)morpholine forms classical types of bonds with chosen biotargets. The key amino acid residues involved in the formation of complexes were also identified. Based on the binding profiles observed for selected complexes with the active centers of thymidine kinase (4IVR), phosphate synthase (1G6C), and biotin carboxylase (2W6O), it can be concluded that this bioactive ligand is likely to exhibit antibacterial and antiviral effects by inhibiting molecular and biological processes in pathogenic organisms. The chosen targets had acceptable binding modes with 4-((5-(decylthio)-4-methyl-4H-1,2,4-triazole3-yl)methyl)morpholine, did not form unwanted contacts, and interacted with some critically important amino acid residues. This suggests the potential for further use in virtual screening, computer modeling, and more in-depth in vitro and in vivo studies. The results of the multitarget analysis could contribute to the development of new antimicrobial drugs effective against various types of infectious agents. [ABSTRACT FROM AUTHOR]

The title compound, bis[μ-2,2′-(4H-1,2,4-triazole-3,5-diyl)diacetato]bis[diaquacopper(II)] dihydrate, [Cu2(C6H5N3O4)2(H2O)4]·2H2O, is a dinuclear octahedral CuII triazole-based complex. The central copper atoms are hexa-coordinated by two nitrogen atoms in the equatorial positions, two equatorial oxygen atoms of two carboxylate substituents in position 3 and 5 of the 1,2,4-triazole ring, and two axial oxygen atoms of two water molecules. Two additional solvent water molecules are linked to the title molecule by O—H...N and O...H—O hydrogen bonds. The crystal structure is built up from the parallel packing of discrete supramolecular chains running along the a-axis direction. Hirshfeld surface analysis suggests that the most important contributions to the surface contacts are from H...O/O...H (53.5%), H...H (28.1%), O...O (6.3%) and H...C/C...H (6.2%) interactions. The crystal studied was twinned by a twofold rotation around [100].

This study presents the synthesis, characterization and Hirshfeld surface analysis of the title mononuclear complex, [PdCl2(C12H14N4)]·C3H7NO. The compound crystalizes in the P21/c space group of the monoclinic system. The asymmetric unit contains one neutral complex Pd(HLc-Pe)Cl2 [HLc-Pe is 2-(3-cyclopentyl-1,2,4-triazol-5-yl)pyridine] and one molecule of DMF as a solvate. The Pd atom has a square-planar coordination. In the crystal, molecules are linked by intermolecular N—H...O and C—H...N hydrogen bonds, forming layers parallel to the bc plane. A Hirshfeld surface analysis showed that the H...H contacts dominate the crystal packing with a contribution of 41.4%. The contribution of the N...H/H...N and H...O/O...H interactions is somewhat smaller, amounting to 12.4% and 5%, respectively.

In the title complex, [U(C10H7N3O3)O2(CH3OH)]n, the UVI cation has a typical pentagonal–bipyramidal environment with the equatorial plane defined by one N and two O atoms of one doubly deprotonated 2-[5-(2-hydroxyphenyl)-1H-1,2,4-triazol-3-yl]acetic acid ligand, a carboxylate O atom of the symmetry-related ligand and the O atom of the methanol molecule [U—N/Oeq 2.256 (4)–2.504 (5) Å]. The axial positions are occupied by two oxide O atoms. The equatorial atoms are almost coplanar, with the largest deviation from the mean plane being 0.121 Å for one of the O atoms. The benzene and triazole rings of the tetradentate chelating–bridging ligand are twisted by approximately 21.6 (2)° with respect to each other. The carboxylate group of the ligand bridges two uranyl cations, forming a neutral zigzag chain reinforced by a strong O—H...O hydrogen bond. In the crystal, adjacent chains are linked into two-dimensional sheets parallel to the ac plane by C/N—H...N/O hydrogen bonding and π–π interactions. Further weak C—H...O contacts consolidate the three-dimensional supramolecular architecture. In the solid state, the compound shows a broad medium intensity LMCT transition centred around 463 nm, which is responsible for its red colour.

Src homology‐2 (SH2) domain‐containing phosphatase‐2 (SHP2), the first protooncogenic phosphatase is a key mediator in the development and progression of various cancers. Several allosteric sites have been identified in SHP2, inhibitors of which are being developed. In the current study, we have designed and synthesized a library of 21 thioacetamide‐tethered thiadiazole‐1,2,4‐triazole hybrids (compounds 16–36) and evaluated their in vitro SHP2 inhibitory potential. Compound 28 (N‐(5‐(benzo[d][1,3]dioxol‐5‐yl)‐1,3,4‐thiadiazol‐2‐yl)‐2‐((5‐(4‐methoxyphenyl)‐4H‐1,2,4‐triazol‐3‐yl)thio)acetamide) emerged as the most potent SHP2 inhibitor (IC50=0.318±0.001 μM) inhibiting the enzyme in a mixed to non‐competitive manner. In silico studies revealed that the lead inhibitor strongly binds to the tunnel allosteric site of SHP2. Further, cytotoxicity studies revealed that compound 28 caused death of SHP2‐driven MCF‐7 (GI50=37.02±0.25 μM) and U87MG cells (GI50=68.69±0.21 μM) in a dose‐dependent manner and inhibited MCF‐7 cell colony formation and migration. Flow cytometric analysis showed that it exerted its antiproliferative effect on U87MG cells by inducing early apoptosis (Q2 phase) and inhibiting cell cycle progression at the G1 and S phase. Compound 28 was shown to increase oxidative stress in the U87 cells by promoting ROS generation and loss of mitochondrial integrity. In summary, the present study produced a potent SHP2 inhibitor (compound 28) with a promising in vitro cytotoxicity profile, thus meriting further investigation. [ABSTRACT FROM AUTHOR]

In the title complex, [U(C10H7N3O3)O2(CH3OH)]n, the UVI cation has a typical penta­gonal-bipyramidal environment with the equatorial plane defined by one N and two O atoms of one doubly deprotonated 2-[5-(2-hy­droxy­phen­yl)-1H-1,2,4-triazol-3-yl]acetic acid ligand, a carboxyl­ate O atom of the symmetry-related ligand and the O atom of the methanol mol­ecule [U--N/Oeq 2.256 (4)-2.504 (5) Å]. The axial positions are occupied by two oxide O atoms. The equatorial atoms are almost coplanar, with the largest deviation from the mean plane being 0.121 Å for one of the O atoms. The benzene and triazole rings of the tetra­dentate chelating-bridging ligand are twisted by approximately 21.6 (2)° with respect to each other. The carboxyl­ate group of the ligand bridges two uranyl cations, forming a neutral zigzag chain reinforced by a strong O--H...O hydrogen bond. In the crystal, adjacent chains are linked into two-dimensional sheets parallel to the ac plane by C/N--H...N/O hydrogen bonding and π-π inter­actions. Further weak C--H...O contacts consolidate the three-dimensional supra­molecular architecture. In the solid state, the compound shows a broad medium intensity LMCT transition centred around 463 nm, which is responsible for its red colour. [ABSTRACT FROM AUTHOR]

A simple and economical approach has been proposed for the transformation of 2-(quinolyl-propanoyl)-N-phenylhydrazine-1-carbothioamide into 4-methyl-3-[2-(4-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethyl]quinolin-2(1H)-ones and 3-[2-(5-anilino-1,3,4-thiadiazol-2-yl)ethyl] 4-methylquino-lin-2(1H)-ones by heterocyclization in the presence of aqueous sodium hydroxide and concentrated sulfuric acid, respectively. The reactions are economically efficient, and the target products are formed in high yields (85–98%) under mild conditions without using expensive catalysts and column chromatography for their isolation. [ABSTRACT FROM AUTHOR]

Various bi- and polycyclic pyrimidine derivatives (including fused ones) containing different aza- and carbocyclic fragments have been synthesized via a modified Biginelli reaction. [ABSTRACT FROM AUTHOR]

The research is aimed at solving one of the fundamental problems of organic chemistry — to combine groups with antagonistic properties in one molecule, viz., an oxidizing (peroxide) group and a reducing (N-containing) group. Stable hybrid compounds containing 1,2,4,5-tetraoxane and triazole or imidazole moieties were obtained for the first time. Most of the synthesized hybrid compounds showed fungicidal activity in vitro against phytopathogenic fungi of different taxonomic classes, which is comparable or superior to the comparison preparations triadimefon and kresoxim-methyl. [ABSTRACT FROM AUTHOR]

We report the synthesis, spectroscopic properties, and anti-proliferative efficacy of the adamantane-linked 1,2,4-triazole derivative 5-(adamantan-1-yl)-4-(3-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione. Crystal packing and intermolecular interactions have been quantified using Hirshfeld surfaces and two-dimensional fingerprint plots. ADMET characteristics, bioavailability, and drug-likeness define the compound's bioactivity. The gastrointestinal absorption is anticipated to be high, and the projected bioavailability score is 0.55. The topological polar surface area and iLOGP, XLOGP, WLOGP, and MLOGP lipophilicity parameters have been calculated to be 65.70 Å2, 3.24, 4.74, 5.05, and 4.07, respectively. To investigate 5A4ClT's EGFR inhibition and its use in the treatment of non-small cell lung cancer, Autodock Vina was used to dock it with the crystal structure of the EGFR kinase domain protein. The title chemical hydrophobically interacts with the receptor residues LEU718, VAL726, ALA743, GLU762, THR790, LEU792, MET793, GLY796, ARG841, ASN842, and LEU844 and forms hydrogen bonds with ASP855 and THR854 with an affinity of −8.3 kcal/mol. Toxicity end points and comparison with NSCLC drugs yielded promising findings. 120 ns molecular dynamics simulations confirmed the ligand's dynamic stability in the target protein's binding pocket. This research lays the groundwork for future in vivo investigations of 5A4ClT as a non-small cell lung cancer therapy. [ABSTRACT FROM AUTHOR]

An efficient method for the synthesis of 1-substituted 5-aryl-1,2,4-triazoles by selective C—H arylation of 1-substituted 1,2,4-triazoles with non-activated aryl chlorides and aryl bromides under the catalysis by a palladium complex with a N-heterocyclic carbene ligand IPr*OMe using 1,1,2,2-tetraphenylethane-1,2-diol (TPEDO) as a catalyst activator is reported. [ABSTRACT FROM AUTHOR]

In this work, 1,2,4-triazole derived hydrazide–hydrazones were synthesized with a five-step synthesis pathway. The novel derivatives were characterized by various analytical methods. Acetylcholinesterase (AChE), and human carbonic anhydrase (hCA) inhibitory qualifications of these thirteen original compounds (4, 5a–l) were also determined. The overall biological activity results were very interesting. The reported compounds were found to be very effective inhibitors of hCA I, hCA II, and AChE enzymes with IC50 values in the range of 17.33−77.00 nM for hCA I (Acetazolamide IC50: 62.80 nM), 13.07−46.20 nM for hCA II (Acetazolamide IC50: 57.75 nM) and 4.91−36.47 nM for AChE (Tacrine IC50: 28.88 nM). Within the new compounds, 5i displayed the best hCA I, hCA II and AChE inhibitory activities with IC50 values of 17.33 nM, 13.07 nM, and 4.91 nM, respectively. [ABSTRACT FROM AUTHOR]

We have synthesized 1,2,4-triazole bearing benzenesulfonohydrazide analogues (1–21), characterized through different spectroscopic techniques such as 1HNMR, 13CNMR, HREI-MS and were evaluated against Acetylcholinesterase (AChE) and Butyrylcholinesterase (BuChE) enzymes. All the newly synthesized analogues showed excellent to good inhibition potential with IC50 values ranged from 0.30 ± 0.050 to 15.21 ± 0.50 µM (against AChE) and 0.70 ± 0.050 to 18.27 ± 0.60 µM (against BuChE) as compared to the standard drug Donepezil (IC50 = 2.16 ± 0.12 and 4.5 ± 0.11 µM, respectively). Analogues 2 and 4 which were found inactive against these enzymes. However, analogues 17 (IC50 = 0.30 ± 0.050 and 0.70 ± 0.050 µM) and 13 (IC50 = 0.70 ± 0.05 and 1.70 ± 0.050 µM) were found to have potent inhibitory potentials against the targeted enzymes. Structure-activity relationship was carried out which mainly depends upon the nature, position and numbers of the substitution present on phenyl rings that may be electron withdrawing/donating. Molecular docking study was carried out to know about the binding mode of interaction of the most active site of the synthesized analogues with the targeted enzymes.

The title compound, C27H20N4O3S, crystallizes in the monoclinic system, space group P21/n, with Z = 4. The global shape of the molecule is determined by the orientation of the substituents on the central 4H-1,2,4-triazole ring. The nitrophenyl ring, phenyl ring, and naphthalene ring system are oriented at dihedral angles of 82.95 (17), 77.14 (18) and 89.46 (15)°, respectively, with respect to the triazole ring. The crystal packing features chain formation in the b-axis direction by S...O interactions. A Hirshfeld surface analysis indicates that the highest contributions to surface contacts arise from contacts in which H atoms are involved.

The title compound, [Cu(HL)2(H2O)2] or [Cu(C4H4N3O2)2(H2O)2], is a mononuclear octahedral CuII complex based on 5-methyl-1H-1,2,4-triazole-3-carboxylic acid (H2L). [Cu(HL)2(H2O)2] was synthesized by reaction of H2L with copper(II) nitrate hexahydrate (2:1 stoichiometric ratio) in water under ambient conditions to produce clear light-blue crystals. The central Cu atom exhibits an N2O4 coordination environment in an elongated octahedral geometry provided by two bidentate HL− anions in the equatorial plane and two water molecules in the axial positions. Hirshfeld surface analysis revealed that the most important contributions to the surface contacts are from H...O/O...H (33.1%), H...H (29.5%) and H...N/N...H (19.3%) interactions.

Biological evaluation of a 1,2,4-triazole mannich base that has been synthesized for interesting behavior in medicinal chemistry, so it’s interesting to synthesize triazole derivatives and investigate their biological properties to evaluate their capacity in medicine. The aim of this study evaluate the antimicrobial, anticancer, and antioxidant activities of a 1,2,4-triazole Mannich base derivative and its power in the treatment of diseases. For antimicrobial activity four bacterial strains and one fungal strain based on the agar disc diffusion. While used two cancer cell lines for anticancer activity which are known as Hep-G2 and MCF-7; the antioxidant activity of the compound used three different radical species include OH•, ABTS•+, and DPPH•, and also determine the antioxidant activity of the compound after extracting vitamins A, C, E, and MDA in the S. cerevisiae yeast cell by HPLC. The results of this study show the positive role of a derivative 1,2,4-triazole mannich base as antimicrobial and antiradical assays, particularly when treated with C. albicans and OH• radical that significantly reduced growth of the fungal and the radical compared to others. In addition, it didn’t exhibit any cytotoxicity to reduce both cancer cell lines. In conclusion, the compound's ability is different from one assay to another, increasing its concentration efficiency affects the radical scavenging, and inhibits microorganism growth.

AbstractThe study investigated the corrosion-inhibitory properties of three synthetic triazole Mannich bases on C1018 carbon steel using various electrochemical techniques. The inhibitors, namely 4-amino-2-[(4-methylpiperazin-1-yl)methyl]-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (4MPT), 4-amino-2-[(piperidin-1-yl)methyl]-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (PPT) and 4-amino-2-[(morpholin-4-yl)methyl]-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (MPT), demonstrated the high inhibition efficiencies of 92.8%, 93.3% and 92.6%, respectively, and adhered to the Langmuir adsorption isotherm. The inhibitors also functioned as mixed-type inhibitors and improved the protective layer on the metal surface. The study also utilized scanning electron microscopy - energy dispersive x-ray (SEM-EDX) analysis to examine the surface morphology of the uninhibited and inhibited carbon steel specimens. Furthermore, density functional theory (DFT) was utilized for theoretical calculations, which corroborated with experimental measurements.

5-(Tert-butyl)-N-(2,4-dichlorophenyl)-1H-1,2,4-triazol-3-amine was synthesized in four steps starting from pivalic acid via thiourea formation followed by heterocyclization with hydrazine hydrate. The structure was established by spectroscopic data, elemental analysis, and substantiated by single-crystal X-ray crystallography. It crystallizes in orthorhombic crystal system with Pbca as space group. In crystal structure, the intermolecular N–H···N hydrogen bonds link the molecules which stabilize the structure. Density functional theory (DFT) calculations have been performed to gain insights into the electronic structure of the compound. The inhibitory activity of the compound against the Jack bean urease revealed significant inhibition IC50 value 0.21 ± 0.2 μM (~ 100-folds higher than standard). The Hirshfeld surface is an external 3D curve of electrostatic potential in space over a particular molecule in crystalline state. Hirshfeld surface analysis and 2D fingerprint plots were performed. The evaluation of the electrostatic, dispersion, and total energy frameworks indicates that the stabilization is dominated via the electrostatic energy contribution. The molecular docking of compound exhibited hydrogen bonding and C-H-π interaction with docking energy score of − 6.68 and − 6.46 kcal/mol respectively. The compound was also evaluated for antioxidant scavenging activities against DPPH and showed promising antioxidant property with an IC50 value of 0.45 μg/mL. In addition, the compound was also tested for cytotoxicity using brine shrimp lethality bioassay and LD50 was found to be 0.5 μg/mL. DNA protection assay was performed with human blood DNA and DNA cleavage was protected by compound at or above 6 μM concentration. Furthermore, DNA titration by UV-visible spectroscopy for compound's interaction with DNA revealed substantial (Kb; 1.605 × 103 M−1) and spontaneous (ΔG; − 19.023 kJmol−1) interaction via intercalation and the linear rise in DNA viscosity in the presence of compound's concentrations further verified the intercalation binding mode. [ABSTRACT FROM AUTHOR]

The newly synthesized quinoxaline-1,2,4-triazole-3-amide conjugates through a multistep method. The prepared compounds were screened for their anticancer activity against secreted human cancer cell lines such as DU-145 (prostate), MCF-7 (breast), and A549 (lung) by applying the MTT method, and the standard drug etoposide was used as a reference drug. The activity results show that two compounds, namely 3,5-dimethoxy-N-(5-{[2-oxoquinoxalin-1(2H)-yl]methyl}-4H-1,2,4-triazol-3-yl)benzamide and 4-methoxy-N-(5-{[2-oxoquinoxalin-1(2H)-yl]methyl}-4H-1,2,4-triazol-3-yl)benzamide exhibited more potent activity than the standard drug. Whereas, two compounds, 3-methoxy-N-(5-{[2-oxoquinoxalin-1(2H)-yl]methyl}-4H-1,2,4-triazol-3-yl)benzamide, and 3,4-dimethoxy-N-(5-{[2-oxoquinoxalin-1(2H)-yl]methyl}-4H-1,2,4-triazol-3-yl)benzamide showed very similar activity against tested cell lines to that of the standard drug IC50 value. The in vitro tyrosine kinase EGFR inhibitory activity results indicate that two compounds, 3,5-dimethoxy-N-(5-{[2-oxoquinoxalin-1(2H)-yl]methyl}-4H-1,2,4-triazol-3-yl)benzamide and 4-methoxy-N-(5-{[2-oxoquinoxalin-1(2H)-yl]methyl}-4H-1,2,4-triazol-3-yl)benzamide exhibited more activity than the standard drug etoposide. [ABSTRACT FROM AUTHOR]

In search of 1,2,4-triazole-based antidiabetic agents, new mixed-ligand chelates of the type, [M(L)(H2O)3] (where M = Co(II), Ni(II), Cu(II) and Zn(II)), were synthesized using 2-(((3-mercapto-5-(pyridin-3-yl)-4H-1,2,4-triazol-4-yl)imino)methyl)-4-nitrophenol (H2L1) ligand and the corresponding metal acetates in 1:1 molar ratio. FTIR, NMR, mass, UV–Vis, elemental analyses, conductivity measurements, ESR, XRD, TGA, SEM, and EDAX studies were used to determine the nature of bonding, coordination characteristics and the stability of compounds. Spectral and physico-analytical studies suggest that the ligand functioned in a binegative tridentate manner with phenolic-O, azomethine-N and thiol-S as the coordinating sites and an octahedral geometry was proposed for the metal complexes. The quantum computational calculations of the synthesized compounds were executed in the ground state using DFT/B3LYP level with 6-311++G as basis set. In vitro alpha-amylase and alpha-glucosidase inhibitory assay revealed moderate to good results for the synthesized compounds and especially the complex 3 against alpha-amylase and complex 4 against alpha-glucosidase were found to be effective inhibitors. Additionally, the compounds were explored for molecular docking studies against the human pancreatic alpha-amylase (PDB id: 1BSI) and alpha-glucosidase (PDB id: 5ZCC). The molecular docking calculations of complex 3 into 1BSI revealed a binding energy of − 8.6 kcal/mol, whereas that of complex 4 against 5ZCC resulted in a binding energy of − 7.4 kcal/mol respectively, both of which exceeds that of the standard Acarbose. New Schiff base ligand and its transition metal chelates were synthesized. Furthermore, the synthesized compounds were examined for in vitro alpha-amylase and alpha-glucosidase inhibitory activity. [ABSTRACT FROM AUTHOR]

A new silver(I) cluster [Ag8L4(Py)(Pype)]·4Py·11H2O (I) with 3-benzyl-4-phenyl-1,2,4-triazol-5-thiol (L) was synthesized via the direct reaction of AgNO3 and L in MeOH, followed by recrystallization from a pyridine–piperidine mixture. The compound I was isolated in a monocrystal form and its crystal structure was determined via single crystal X-ray diffraction. The complex forms a "butterfly" cluster with triazol-5-thioles. The purity of the silver complex and its stability in the solution was confirmed via NMR analysis. Excitation and emission of the free ligand and its silver complex were studied at room temperature for solid samples. The in vitro biological activity of the free ligand and its complex was studied in relation to the non-pathogenic Mycolicibacterium smegmatis strain. Complexation of the free ligand with silver increases the biological activity of the former by almost twenty times. For the newly obtained silver cluster, a bactericidal effect was established. [ABSTRACT FROM AUTHOR]

In the current study, a series of 1,3,4-oxadiazole and 1,2,4-triazole derivatives linked to quinazolinone were designed and synthesized by using Phase Transfer Catalysis. The structures of the synthesized compounds were confirmed by their IR, 1H NMR, 13C NMR, and HR-ESI-MS spectroscopic data, and their in vitro antiproliferative activities against A549, Hela, MCF-7 as well as L929 were detected by using CCK-8 assay. The results demonstrated that most of the compounds showed better growth inhibitory effect than 5-FU on A549, Hela, and MCF-7 cell lines. Especially, 2-(5-((3-bromophenyl)thio)-1,3,4-oxadiazole-2-yl)quinazolin-4(3H)-one (8o), 4-amino-5-((4-nitrophenyl)thio)-4H-1,2,4-triazol-3-yl)quinazolin-4(3H)-one (9m) and 2-(4-amino-5-(o-tolylthio)-4H-1,2,4-triazol-3-yl)quinazolin-4(3H)-one (9b) showed good antiproliferative activity against A549 cells with IC50 value of 3.46, 2.96, and 3.44 μM, respectively. 2-(4-Amino-5-((3,5-difluorophenyl)thio)-4H-1,2,4-triazol-3-yl)quinazolin-4(3H)-one (9h) and 4-amino-5-((4-nitrophenyl)thio)-4H-1,2,4-triazol-3-yl)quinazolin-4(3H)-one (9m) had obvious inhibitory effects on Hela cells with IC50 values of 1.76 and 3.91 μM, respectively. 2-(4-Amino-5-((2-chlorophenyl)thio)-4H-1,2,4-triazol-3-yl)quinazolin-4(3H)-one (9i) showed high inhibitory activity against MCF-7 cells with IC50 value of 2.72 μM. Meanwhile, all compounds showed lower cytotoxicity to L929 cells than positive control drug 5-FU. In development, according to the above preliminary observation, these novel quinazolinones incorporating 1,3,4-oxadiazole and 1,2,4-triazole thioether moieties could become potential molecular templates for searching new antitumor agents. [ABSTRACT FROM AUTHOR]

The title compound, [Cu(HL)2(H2O)2] or [Cu(C4H4N3O2)2(H2O)2], is a mononuclear octahedral CuII complex based on 5-methyl-1H-1,2,4-triazole-3-carboxylic acid (H2L). [Cu(HL)2(H2O)2] was synthesized by reaction of H2L with copper(II) nitrate hexahydrate (2:1 stoichiometric ratio) in water under ambient conditions to produce clear light-blue crystals. The central Cu atom exhibits an N2O4 coordination environment in an elongated octahedral geometry provided by two bidentate HL- anions in the equatorial plane and two water molecules in the axial positions. Hirshfeld surface analysis revealed that the most important contributions to the surface contacts are from H. . .O/O. . .H (33.1%), H. . .H (29.5%) and H. . .N/N. . .H (19.3%) interactions. [ABSTRACT FROM AUTHOR]

A novel series of bis([1,2,4]triazolo)[4,3‐a][4′,3′‐c] quinazolines derivatives 2 a–2 o has been synthesis in good to excellent yields (74–86 %) under mild reaction conditions via bis(trifluoroacetoxy)iodobenzene (PIFA) mediated oxidative‐cyclization of corresponding 2,4‐bis(2‐(E)‐arylidenehydrazinyl) quinazolines 1 a–1 o. Formation of the targeted compounds has been supported using various spectroscopic tools (IR, 1H & 13 C‐NMR) and HRMS analysis. These bis([1,2,4]triazolo)[4,3‐a][4′,3′‐c] quinazolines derivatives were biologically screened for their antiproliferative activities against MCF‐7 cancer cells. Results indicate that among all synthesized derivatives, 3,7‐bis (4‐chlorophenyl) bis([1,2,4]triazolo)[4,3‐a : 4′,3′‐c]quinazoline (2 d) and 3,7‐bis(3‐methoxyphenyl)bis([1,2,4]triazolo)[4,3‐a : 4′,3′‐c]quinazoline (2 j) displayed uppermost cytotoxicity efficacy with GI50 value of 106.30 μM and 108.56 μM respectively. Furthermore, molecular docking studies have been carried out to investigate possible binding modes between active sites of the protein (PDB ID: 3 U6 J) and the target compounds. In addition to these results, ADME (adsorption, distribution, metabolism, excretion) analysis has also been carried out to study the pharmacokinetic properties of the targeted compounds. [ABSTRACT FROM AUTHOR]

A three-stage method was proposed for the synthesis of new 4-[4-(2-azolylethyl)piperazine-1-yl]-N-aryl-5H-1,2,3-dithiazole-5-imines. This approach includes the reaction of Appel salt with anilines to produce 1,2,3-dithiazole-5-imines, which were converted into 4-[(4-chloroethyl)piperazine-1-yl]-5H-1,2,3-dithiazole-5-imines, alkylating azoles at the final stage. The high fungicidal activity of target compounds and intermediate 4-chloro-N-aryl-1,2,3-dithiazole-5-imines was shown in vitro tests versus six species of phytopathogenic fungi. [ABSTRACT FROM AUTHOR]

A procedure was developed for preparing 2-alkylthio-5-(1,2,4-triazol-1-ylmethyl)-1,3,4-oxadiazoles by alkylation of 5-(1Н-1,2,4-triazol-1-ylmethyl)-1,3,4-oxadiazole-2-thione with β-bromophenetoles in the presence of triethylamine in acetone with up to 90% yield. The in vitro tests of the target compounds for fungicidal activity toward six species of phytopathogenic fungi of different taxonomic classes show that the S-halophenoxyethyl-substituted derivatives surpass a reference fungicide, Triadimefon, in the activity toward Venturia inaequalis, Rhizoctonia solani, and Bipolaris sorokiniana. [ABSTRACT FROM AUTHOR]

The pyrido[2,3‐d]pyrimidine moieties are one of the most biologically widespread heterocyclic compounds as antimicrobial, antioxidant, antitubercular, antiviral and anti‐inflammatory. Hence, we synthesized an efficient new series of 2‐thioxo‐pyrido[2,3‐d]pyrimidinone, 2‐hydrazinyl‐(quinolin‐2‐yl)pyrido[2,3‐d]pyrimidinone,N′‐(quinolin‐2‐yl)‐pyrido[2,3‐d]pyrimidine‐(formo/aceto)‐hydrazide and substituted‐(quinolin‐2‐yl)pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidinone derivatives. The characterization of new compounds was corresponded by using spectroscopic techniques, IR, NMR and Mass spectra. In vitro, all compounds were evaluated as antimicrobial activity compared with cefotaxime sodium and nystatin as the standard drug. This work deals with the exploration of the new heterocyclic compounds and medicinal diversity of quinoline‐pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidine derivatives that might pave the way for long in the discovery of therapeutic medicine for future drug design. [ABSTRACT FROM AUTHOR]

The study investigated the corrosion-inhibitory properties of three synthetic triazole Mannich bases on C1018 carbon steel using various electrochemical techniques. The inhibitors, namely 4-amino-2-[(4-methylpiperazin-1-yl)methyl]-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (4MPT), 4-amino-2-[(piperidin-1-yl)methyl]-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (PPT) and 4-amino-2-[(morpholin-4-yl)methyl]-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (MPT), demonstrated the high inhibition efficiencies of 92.8%, 93.3% and 92.6%, respectively, and adhered to the Langmuir adsorption isotherm. The inhibitors also functioned as mixed-type inhibitors and improved the protective layer on the metal surface. The study also utilized scanning electron microscopy - energy dispersive x-ray (SEM-EDX) analysis to examine the surface morphology of the uninhibited and inhibited carbon steel specimens. Furthermore, density functional theory (DFT) was utilized for theoretical calculations, which corroborated with experimental measurements. [ABSTRACT FROM AUTHOR]

Recently, heterocyclic compounds such as pyrido [2,3-d] pyrimidinones, 1,2,4-triazolopyrimidines, pyrimidoquinazolines, and quinoline derivatives have gained attention from researchers due to their pharmacological and biological activities. To synthesize new compounds, quinoline-2-thioxopyrido [2,3-d] pyrimidinone (1) and methylthioquinoline-pyrido [2,3-d] pyrimidinones (2) were used as starting materials. The new compounds synthesized were quinoline-pyrido [2,3-d] (DeGoey et al., 2013; Gouda et al., 2020; Dangolani et al., 2018) [1, 2,4]triazolopyrimidinones (5a-d), 2-methylsulfonyl-quinoline-pyrido [2,3-d]pyrimidinone (6), pyrido [2,3-d]pyrimidine derivatives, pyridopyrimido (Gouda et al., 2020; DeGoey et al., 2013) 2,12,1-b] quinazoline (9), pyrido [(Khajouei et al., 2021; Gouda et al., 2020) 3,23,2-e]bis (1,2,4-triazole)pyrimidine (12a,b) and pyridopyrimido-diquinazoline-dione (16) derivatives. These compounds were synthesized with high efficiency, producing yields ranging from 69% to 90%, under moderate conditions, through treating (2) or (10) with various reagents such as anthranilic acid, phosphorus oxychloride, hydrazine hydrate, formic acid, glacial acetic acid, arylamine (aniline, 4-chloroaniline, or 4-methoxyaniline), and sec-amine (piperazine or morpholine). The new structures of the synthesized compounds were verified using various spectroscopic procedures, such as IR, NMR, and mass spectra. Molecular docking studies were carried out to investigate and discuss how the prepared compounds bind to amino acids such as Estrogen Receptor alpha, EGFR, and NADPH oxidase protein. Also, the synthesized products were tested for their anticancer and antioxidant activities against the (MCF-7) breast carcinoma cell line and human normal Retina pigmented epithelium cells (RPE-1). The study on the structure-activity relationship (SAR) established a correlation between the chemical structure of the newly synthesized compounds and their anticancer activity. The findings suggest that compounds 5a-d, 9,12a-b, and 16 exhibited promising anticancer activity and antioxidant effects as measured by DPPH inhibition.

New resveratrol-based Schiff base derivatives (1,2,4-triazole Schiff base derivatives 5a-d and hydrazide Schiff base derivatives 7a-d) were designed, synthesized via Schiff base reaction in the presence of H2SO4 as a catalyst in yield (91.13–41.79 %), and characterized by FTIR, 1H NMR, 13C NMR, DEPT-135 and high-resolution mass HRMS (ESI + ) spectroscopy techniques. A cytotoxicity (MTT) assay was applied to determine the cytotoxic activity of the target compounds on three human cells (HepG2, MCF-7, and T47D). The bioassay showed that a majority of target derivatives showed superior inhibitory activity than the parent compound resveratrol. Among them, derivative 7d showed the best cytotoxic activity against breast cancer cell lines (MCF-7 and T47D) (IC50 = 24.62 and 70.92 μM, respectively). Also, derivative 7b exhibited the best cytotoxic activity against the liver cancer cell line HepG2 (IC50 = 67.47 μM) compared to the parent compound resveratrol. These preliminary findings suggest that the resveratrol-based hydrazide Schiff base derivatives are promising anticancer agents that inspire further developments in this area.

Benzodiazepines (BZD) are widely used in neurological disorders. The use of classical benzodiazepines is limited due to side effects. In this study, based on the structure–activity relationship (SAR) of Benzodiazepine receptors, new derivatives of 4-amino-3,5-diphenyl-1,2,4-triazole as benzodiazepine agonists with selective effects were designed and synthesized. Docking studies showed that pharmacophore groups of the designed structures and zolpidem, a benzodiazepine receptor agonist, are properly matched and are located well in the GABA receptor. The triazole group of the compound 4j, N N-(3,5-diphenyl-4H-1,2,4-triazol-4-yl)-2-((4-fluorobenzyl)amino)acetamide, was near the nitrogen moiety of the imidazole ring of zolpidem providing the hydrogen bond acceptor in the suitable direction in the BDZ-binding site of GABAA receptor model (α1β2ϒ2). The compounds were synthesized with acceptable yield and in-vitro affinity for the BZD receptor was determined. Compound 4j had the best affinity for the BZD site of action on GABAA receptor complex (Ki = 2.56 nM and IC50 = 6.10 nM). In addition, the sedative-hypnotic effect, the locomotor activity, and evaluated memory of the novel compounds were assessed by pentobarbital-induced sleeping, open field, and passive avoidance tests respectively. Most of the novel compounds showed significant hypnotic activity with no impairment on learning and memory performance in the mouse. The pharmacological effects of the compounds were antagonized by flumazenil, a BZD antagonist, which confirms the involvement of BZD receptors in the biological effects.

Background and objectives: Researchers have recently focused on the biological and synthetic effects of 1, 2, and 4-triazole fused heterocyclic molecules because they have tremendous medicinal value. The objective of the present study was to carry out the 3D QSAR evaluation on the substituted 1,2, and 4 triazole derivatives for anticancer potential using k-Nearest Neighbor-Molecular Field Analysis (kNN-MFA) method. Methods: Using the molecular design suite, a three-dimensional quantitative structure–activity relationship (3D-QSAR) analysis was undertaken on a series of 4-amino-5-(pyridin3yl)-4H-1, 2, and 4-triazole-3-thiol anticancer drugs (Vlife MDS). This study used a genetic algorithm and a manual selection approach on 20 substituted 1, 2, and 4-triazole derivatives. Based on the genetic algorithm (GA), the 3D-QSAR model was generated. Statistical significance and predictive capacity were evaluated using internal and external validation. Results: The most significant model has a correlation coefficient of 0.9334 (squared correlation coefficient r2 = 0.8713), showing that biological activity and descriptors have a strong relationship. The model exhibited internal predictivity of 74.45 percent (q2 = 0.2129), external predictivity of 81.09 percent (pred r2 = 0.8417), and the smallest error term for the predictive correlation coefficient (pred r2se = 0.1255). The model revealed steric (S 1047––0.0780––0.0451S 927) and electrostatic (E 1002) data points that contribute remarkably to anticancer activity. A molecular field study demonstrates a link between the structural features of substituted triazole derivatives and their activities. Conclusion: The good-to-moderate anticancer potential of compounds confirms the significant pharmacological role of 1,2,4-triazole derivatives. These results could lead to the identification of potential chemical compounds with optimal anticancer activity and minimal side effects.

Silica nanoparticles have become more attractive due to their surface characteristics, versatility, biocompatibility, and morphological and physicochemical properties. For this reason, their use in biological applications has been expanding in recent years. In this study, after functionalizing silica nanoparticles with glycidyl methacrylate monomer, nanocomposites were formed by attaching 1,2,4‐Triazole, 3‐Amino‐1,2,4‐Triazole, and 5‐Aminotetrazole particles to the surface. Notably, the thermal degradation temperature of all nanocomposites was determined to surpass 200 °C. However, it is worth mentioning that despite the favorable water uptake rates observed for MT(7.64 %) and M3(5.98 %) nanocomposites, MT did not exhibit resistance against Fenton chemicals and experienced degradation. It is important to note that the material loss in M3 nanocomposites is minimal, measuring less than 1 %. In order to reveal the antifungal and antibacterial activity of the synthesized nanoparticles, Minimum inhibitory concentration(MIC), as well as Minimum Fungicidal Concentration(MFC) against the yeast strain Saccharomyces cerevisiae, and Minimum Bactericidal Concentration(MBC) values against bacteria strains, Staphylococcus aureus, Enterococcus faecalis and Escherichia coli were determined. The findings of the study indicated that MP, M3, and M5 nanocomposites displayed a moderate level of antibacterial activity. It is noteworthy, however, that the antibacterial activity diminished when triazole was combined with MP at concentrations exceeding 100 mg/mL. [ABSTRACT FROM AUTHOR]

A novel method for synthesizing 1,2,4-triazole- and tetrazole-containing 4H-thiopyrano[2,3-b]quinolines using a new combination of the thio-Michael and aza-Morita–Baylis–Hillman reactions was developed. Target compounds were evaluated for their cytotoxicities and antiviral activities against influenza A/Puerto Rico/8/34 virus in MDCK cells. The compounds showed low toxicity and some exhibited moderate antiviral activity. Molecular docking identified the M2 channel and polymerase basic protein 2 as potential targets. We observed that the antiviral activity of thiopyrano[2,3-b]quinolines is notably affected by both the nature and position of the substituent within the tetrazole ring, as well as the substituent within the benzene moiety of quinoline. These findings contribute to the further search for new antiviral agents against influenza A viruses among derivatives of thiopyrano[2,3-b]quinoline. [ABSTRACT FROM AUTHOR]

The present work concerns proton-conducting composites obtained by replacing the water molecules present in aluminophosphate and silicoaluminophosphate AFI-type molecular sieves (AlPO-5 and SAPO-5) with azole molecules (imidazole or 1,2,4-triazole). Both the introduction of azoles and the generation of Brønsted acid centers by isomorphous substitution in aluminophosphate materials were aimed at improving the proton conductivity of the materials and its stability. In the presented study, AlPO-5 and several SAPO-5 materials differing in silicon content were synthesized. The obtained porous matrices were studied using PXRD, low-temperature nitrogen sorption, TPD-NH3, FTIR, and SEM. The proton conductivity of composites was measured using impedance spectroscopy. The results show that the increase in silicon content of the porous matrices is accompanied by an increase in their acidity. However, this does not translate into an increase in the conductivity of the azole composites. Triazole composites show lower conductivity and significantly higher activation energies than imidazole composites; however, most triazole composites show much higher stability. The different conductivity values for imidazole and triazole composites may be due to differences in chemical properties of the azoles. [ABSTRACT FROM AUTHOR]

A novel series of 1,2,3-triazole/1,2,4-triazole hybrids 5a, 5b, and 6a–i was designed and synthesized as antiproliferative agents targeting aromatase enzymes. The antiproliferative activity of the new hybrids against four cancer cells was studied using Erlotinib as a control. Compounds 6a and 6b demonstrated the highest antiproliferative activity among these hybrids, with GI50 values of 40 nM and 35 nM, respectively. Compound 6b was the most potent derivative, with a GI50 of 35 nM, comparable to Erlotinib's GI50 of 33 nM. Compound 6b inhibited all cancer cell lines with comparable efficacy to Erlotinib. Compounds 5a, 5b, and 6a–i were tested for inhibitory action against aromatase as a potential target for their antiproliferative activity. Results revealed that compounds 6a and 6b were the most potent aromatase inhibitors, with IC50 values of 0.12 ± 0.01 µM and 0.09 ± 0.01 µM, respectively, being more potent than the reference Ketoconazole (IC50 = 2.6 ± 0.20 µM) but less potent than Letrozole (IC50 = 0.002 ± 0.0002). These findings indicated that compounds 6a and 6b had significant aromatase inhibitory action and are potential antiproliferative candidates. The findings were further linked to molecular docking investigations, which gave models of strong interactions with the aromatase domain for inhibitors with high binding scores. [ABSTRACT FROM AUTHOR]

A new series of 1,2,3-triazoles was synthesized by a titania-supported nano gold nanoparticles catalyzed 1,3-dipolar cycloaddition of aromatic azides with a 3-substituted 1,2,4-triazole terminal alkyne. The compounds were tested for antibacterial activity and antiradical efficiency. Further, in silico molecular docking studies were carried out against glucosamine-6-phosphate syntheses (PDB code: 2VF5) protein receptors. Toxicity of the compounds was studied through survival and climbing assays using an in vivo genetic model, Drosophila melanogaster. [ABSTRACT FROM AUTHOR]

A new Ag(I) adduct was synthesized by the reaction of 4-amino-4H-1,2,4-triazole (L) with AgNO3. Its chemical structure was approved to be [Ag2(L)2(NO3)]n(NO3)n utilizing elemental analysis, FTIR spectra, and single crystal X-ray diffraction (SC-XRD). According to SC-XRD, there are two independent silver atoms which are coordinated differently depending on whether the nitrate anion is coordinated or not. The coordination geometry of Ag1 is a slightly bent configuration while Ag2 has a distorted tetrahedral structure. The 4-amino-4H-1,2,4-triazole ligand and one of the nitrate groups adopt bridging mode, which connects the crystallographically independent Ag1 and Ag2 atoms resulting in the formation of two-dimensional coordination polymer. Hirshfeld surface analysis displays that the intermolecular O···H (34.0%), Ag···N (10.6%), H···H (10.4%), Ag···O (9.3%), and N···H (9.0%) contacts are the most abundant interactions. Regarding anticancer activity, the [Ag2(L)2(NO3)]n(NO3)n demonstrates stronger cytotoxic efficacy against lung (IC50 = 3.50 ± 0.37 µg/mL) and breast (IC50 = 2.98 ± 0.26 µg/mL) carcinoma cell lines than the anticancer medication cis-platin. The [Ag2(L)2(NO3)]n(NO3)n complex showed interesting antibacterial and antifungal activities compared to the free components (AgNO3 and 4-amino-4H-1,2,4-triazole). The investigated silver(I) complex exhibits remarkable antibacterial activity against E. coli (MIC = 6.1 µg/mL) that may be on par with Gentamycin (MIC = 4.8 µg/mL). As a result, the newly synthesized Ag(I) complex could be suggested for anticancer and antibacterial treatments. [ABSTRACT FROM AUTHOR]

1,2,4-triazole derivatives were synthesized via a simple and efficient method using a three-component reaction between aldehyde derivatives, semicarbazide and ethanol in piperidinium acetate (Pip[OAc]) as an ionic liquid. All of synthetized compounds were characterized by 1H NMR, 13C NMR, FT-IR techniques and comparison of melting point. Also, after synthesizing these heterocyclic compounds, their antibacterial properties were studied against two G+ bacteria of Staphylococcus aureus and Bacillus subtilis and two G– bacteria of Escherichia coli and Pseudomonas aeruginosa. In addition, the antifungal properties of the synthesized derivatives against Candida albicans were investigated. [ABSTRACT FROM AUTHOR]

Some novel triazole-bearing ketone and oxime derivatives were synthesized from Ibuprofen. In vitro cytotoxic activities of all synthesized molecules against five cancer lines (human breast cancer MCF-7, human lung cancer A549, human prostate cancer PC-3, human cervix cancer HeLa, and human chronic myelogenous leukemia K562 cell lines) were evaluated by MTT assay. In addition, mouse embryonic fibroblast cells (NIH/3T3) were also evaluated to determine the selectivity. Compounds 18, 36, and 45 were found to be the most cytotoxic, and their IC50 values were in the range of 17.46–68.76 µM, against the tested cancer cells. According to the results, compounds 7 and 13 demonstrated good anti-inflammatory activity against the microsomal enzyme prostaglandin E2 synthase-1 (mPGES-1) enzyme at IC50 values of 13.6 and 4.95 µM. The low cytotoxicity and non-mutagenity of these compounds were found interesting. Also, these compounds significantly prevented tube formation in angiogenesis studies. In conclusion, the anti-inflammatory and angiogenesis inhibitory activities of these compounds without toxicity suggested that they may be promising agents in anti-inflammatory treatment and they may be supportive agents for the cancer treatment. [ABSTRACT FROM AUTHOR]

A series of novel 3,3'-(p-tolylazanediyl)di(propanehydrazide) derivatives bearing double sets of thiosemicarbazide, oxadiazolethione, variously N- and S-substituted triazolethione, pyrrole, and hydrazone moieties were synthesized and their molecular structures were confirmed by IR, 1H, 13C NMR spectroscopy and mass spectrometry data. X-ray analysis of 2,2'-[[[(p-tolylazanediyl)bis(ethane-2,1-diyl)]bis(4-phenyl-4H-1,2,4-triazole-5,3-diyl)]bis(sulfanediyl)]bis[1-(p-tolyl)ethan-1-one] crystal has revealed, that the molecules in the crystal are associated by means of intermolecular hydrogen bonds of OH···N type, forming centrosymmetric dimers. The antioxidant activity of the synthesized compounds was screened by a DPPH radical scavenging assay, reducing power assay, and ferric reducing antioxidant power assay. Among the synthesized compounds, 2,2'-[3,3'-(p-tolylazanediyl)bis(propanoyl)]bis(N-phenylhydrazine-1-carbothioamide) has been identified as possessing the highest antioxidant activity, which is 1.25–2 times higher than that of the commercial antioxidant butylated hydroxytoluene. [ABSTRACT FROM AUTHOR]

In this work, nine 6-fluoro-triazolo-benzothiazole derivatives were prepared and evaluated for in vitro antimitotic activity. In addition, in silico study was also done using tubulin protein (PDB: 6QQN) by molecular docking method. Results revealed that TZ2 and TZ9 were the most active compounds with antimitotic action opposing the standard drug, aspirin. Results of molecular docking exhibited the inhibitory potential of triazolo-benzothiazole against tubulin protein. The mitotic study indicates the efficacy of triazolo-benzothiazole analogues in inhibiting the proliferation of cancer cells either by promoting microtubule formation or affecting microtubules, thereby preventing microtubule breakdown. [ABSTRACT FROM AUTHOR]

In this study, a new series of benzoxazolone−thiosemicarbazide/1,2,4‐triazole/1,3,4‐thiadiazole hybrids were designed and synthesized. The structures of novel compounds were elucidated by spectral methods (IR, 1H‐NMR, 13C‐NMR, ESI‐MS) and elemental analyses. Acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibition activity of the compounds were investigated using in vitro Ellman method using donepezil and tacrin as the standards. Although none of compounds showed significant inhibitor activity on BuChE, compounds 2 c, 3 a, 4 a and 5 b displayed good inhibitory activities on AChE with IC50 values of 0.031, 0.049, 0.117 and 0.085 μg/mL, respectively. Molecular docking studies were carried out performed to the interactions with the active site of the enzyme (PDB:4EY7) and enzyme kinetics studies were performed for the most potent AChE inhibitor compound 2 c. [ABSTRACT FROM AUTHOR]

5‐amino‐3‐nitro‐1‐nitramino‐1,2,4‐triazole was synthesized through the nitration reaction of 1,5‐diamino‐3‐nitro‐1,2,4‐triazole, and several energetic salts were prepared based on the reactivity of the acidic proton in nitramino group (−NHNO2). These compounds were fully characterized by NMR (1H and 13C), IR spectroscopy, elemental analysis, and single‐crystal X‐ray diffraction. Their thermal stabilities were analyzed by differential scanning calorimetric (DSC) and Impact and friction sensitivities were determined using standard BAM technology. Moreover, the structural differences between individual compounds were studied to investigate the potential structure‐property relationship. All compounds possess positive heats of formation calculated based on isodesmic reaction to be between 173.7~454.6 kJ ⋅ mol−1. Among them, 5‐amino‐3‐nitro‐1‐nitramino‐1,2,4‐triazole (D=8682 m ⋅ s−1, P=33.0 GPa, IS=0.75 J), hydrazine salt (D=8908 m ⋅ s−1, P=34.9 GPa, IS=0.5 J) and hydroxylamine salt (D=9117 m ⋅ s−1, P=36.7 GPa, IS=2 J) exhibits desirable detonation properties similar to RDX (D=8795 m ⋅ s−1, P=34.9 GPa), calculated by Kamlet‐Jacobs equations and features comparable impact sensitivity with DDNP (IS=1 J). The simple synthetic route, free of heavy metals and superior detonation properties of above compounds make them serve as promising candidate for green primary explosives. [ABSTRACT FROM AUTHOR]