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3-Amino-4,6-dimethylpyrazolopyridine was applied as a precursor for the synthesis of some new pyridopyrazolo-triazine and pyridopyrazolo-triazole derivatives through diazotization, followed by coupling with many 2-cyanoacetamide compounds, ethyl 3-(phenylamino)-3-thioxopropanoate, 3-oxo-N-phenylbutanethioamide, and α-bromo-ketone reagents [namely; 2-bromo-1-(4-fluorophenyl)ethan-1-one, 5-bromo-2-(bromoacetyl)thiophene, 3-(2-bromoacetyl)-2H-chromen-2-one and/or 3-chloroacetylacetone]. The prepared compounds were identified by spectroscopic analyses as IR, 1H NMR, and mass data. The anticancer activity of these pyrazolopyridine analogues was investigated in colon, hepatocellular, breast, and cervix carcinoma cell lines. The pyridopyrazolo-triazine compound 5a substituted with a carboxylate group gave a distinguished value of IC50 = 3.89 µM against the MCF-7 cell line compared to doxorubicin as a reference drug. Also, the pyridopyrazolo-triazine compound 6a substituted with the carbothioamide function gave good activity toward HCT-116 and MCF-7 cell lines with IC50 values of 12.58 and 11.71 µM, respectively. The discovered pyrazolopyridine derivatives were studied theoretically by molecular docking, and this study exhibited suitable binding between the active sides of pyrazolopyridine ligands and proteins (PDB ID: 5IVE). The pyridopyrazolo-triazine compound 6a showed the highest free binding energy (− 7.8182 kcal/mol) when docked inside the active site of selected proteins. [ABSTRACT FROM AUTHOR]

A series of new 6,8-dichloro-imidazo[1,2-a]pyridine derivatives incorporating pyridine, thiazole, and pyrazole ring systems was synthesized. The synthetic strategy of imidazopyridinyl-pyridine hybrids 2 and 3 involves one pot reaction of the precursor 3-acetyl-6,8-dichloro-2-methylimidazo[1,2-a] pyridine (1) with aldehydes, malononitrile, and/or ethyl cyanoacetate. Treatment of 1 with thiosemicarbazide and/or bromine followed by subsequent cyclization with ethyl bromoacetate, chloroacetone, phenacyl chloride, and/or thiourea was applied as synthetic routes for accessing the imidazopyridinyl-thiazole hybrids 5, 6, and 8–10. The reaction of 1 with dimethylformamide-dimethylacetal followed by subsequent treatment with hydrazine was employed to prepare the imidazopyridinyl-pyrazole motif 12. The antibacterial potency of these imidazopyridine hybrids has been evaluated against some model bacteria. The results indicated that the imidazopyridine-thiazole hybrids revealed remarkable antibacterial activities. [ABSTRACT FROM AUTHOR]

Herein, we present a thorough photovoltaic investigation of four triphenylamine organic sensitizers with D–π–A configurations and compare their photovoltaic performances to the conventional ruthenium-based sensitizer N719. SFA-5–8 are synthesized and utilized as sensitizers for dye-sensitized solar cell (DSSC) applications. The effects of the donor unit (triphenylamine), π-conjugation bridge (thiophene ring), and various acceptors (phenylacetonitrile and 2-cyanoacetamide derivatives) were investigated. Moreover, this was asserted by profound calculations of HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) energy levels, the molecular electrostatic potential (MEP), and natural bond orbital (NBO) that had been studied for the TPA-sensitizers. Theoretical density functional theory (DFT) was performed to study the distribution of electron density between donor and acceptor moieties. The sensitization by the absorption of sensitizers SFA-5–8 leads to an obvious enhancement in the visible light absorption (300–750 nm) as well as a higher photovoltaic efficiency in the range of (5.53–7.56%). Under optimized conditions, SFA-7 showed outstanding sensitization of nanocrystalline TiO2, resulting in enhancing the visible light absorption and upgrading the power conversion efficiency (PCE) to approximately 7.56% over that reported for the N719 (7.29%). Remarkably, SFA-7 outperformed N719 by 4% in the total conversion efficiency. Significantly, the superior performance of SFA-7 could be mainly ascribed to the higher short-circuit photocurrents (Jsc) in parallel with larger open-circuit voltages (Voc) and more importantly, the presence of different anchoring moieties that could enhance the ability to fill the gaps on the surface of the TiO2 semiconductor. That could be largely reflected in the overall enhancement in the device efficiency. Moreover, the theoretical electronic and photovoltaic properties of all studied sensitizers have been compared with experimental results. All the 2-cyanoacrylamide derivative sensitizers demonstrated robust photovoltaic performance. [ABSTRACT FROM AUTHOR]

A novel series of benzothiazolopyridine derivatives was synthesized via interaction of -2- (benzothiazol-2-yl)-3-(4-chlorophenyl)acrylonitrile (2) with a diverse of commercially available reagents (indandione, thiobarbituric acid, and malononitrile). Moreover, a novel group of benzothiazole linked substituted 1,2,3-triazole derivatives were synthesized by exploring the chemical behavior of 5-benzothiazolyl-2-(4-chlorophenyl)-triazol-4-amine through refluxing in glacial acetic acid, condensation with phthalic anhydride, and cyanoacetylation reactions. All newly synthetized compounds have been tested for their antioxidant and antibacterial activities compared with ascorbic acid and Ampicillin as reference drugs, respectively. The benzothiazolopyridopyrimidine compound 6 was found the most potent antioxidant agent with IC50 = 0.015 mg/mL compared to the results of ascorbic acid (IC50 = 0.022 mg/mL). The investigated compounds showed no antibacterial properties against Gram-negative bacterial species, Pseudomonas aeruginosa and Escherichia coli. Benzothiazolopyridine derivative 5 displayed the best growth inhibition against Gram-positive bacteria, Staphylococcus aureus and Bacillus cereus with inhibition zones 24 and 20 mm, respectively. [ABSTRACT FROM AUTHOR]

The versatile scaffold, N'-(2-cyanoacetyl)-2-hydroxybenzohydrazide (3) was utilized in the production of new pyridine, chromene and thiazole derivatives as antimicrobial and antioxidant agents. The synthetic strategy involves the treatment of precursor 3 with various arylidene-malononitrile and 3-aryl-2-cyanoacrylate compounds to furnish substituted pyridines 5 and 7. The interaction of 3 with salicylaldehyde and/or phenyl isothiocyanate followed by cyclization with chloroacetone produced the corresponding 2-imino-2Hchromene-3-carbohydrazide and (thiazol-2-ylidene-acetyl)-salicylic acid hydrazide compounds 8 and 9, respectively. The structural features of the synthesized compounds were confirmed by using spectroscopic methods such as (IR, 1H NMR, 13C NMR and MS). The new pyridine, chromene and thiazole products showed potent antioxidants and antimicrobial activities. The thiazole derivative 9 exhibited the highest anti-bacterial and antifungal activities against S. aureus (75.0%) and B. subtilis (73.9%) and C. albicans (66.6%). The combination between salicylic acid hydrazide and thiazole moieties in the hybrid 9 indicated the best antioxidant activity (87.9%). [ABSTRACT FROM AUTHOR]

4-Aminobenzohydrazide (1) undergoes chloroacetylation twice, at the primary amine and hydrazide-NH2 functional groups. The conforming bis-chloroacetamide derivative 3 was reacted with different sulfur reagents (namely, 2-mercaptobenzothiazole, 6-amino-2-mercaptopyrimidin-4-ol, and 2-mercapto-4,6-dimethyl-nicotinonitrile) to give new bis-sulfide compounds 5, 7 and 9, respectively. The newly synthesised bis-chloroacetamide and corresponding sulfides were screened for anti-microbial and antioxidant potential. The sulfide derivative 7 exhibited the most potent activity against Staphylococcus aureus and Pseudomonas aeruginosa. It shows inhibition activities of 83.4% and 78.8%, respectively. Moreover, the sulfide derivative 7 showed the highest antioxidant activity with an inhibition ratio of 85.9%, which is close to L-ascorbic acid. [ABSTRACT FROM AUTHOR]

The bimetallic complexes of 2,2′‐malonylbis(N‐phenylhydrazine‐1‐carbothioamide) have been prepared and characterized by elemental and spectral analyses. The free ligand exists in keto‐thione form, whereas in complexes it chelated to the metal ion in binegative tetradentate and neutral tetradentate manners. The electronic spectra and magnetic moment measurements showed that all the complexes have an octahedral geometry except the [Cu2(H2L)(OAc)2]EtOH complex which has square planar structure supported by the electron spin resonance (ESR) spectral data. In addition, thermal gravimetric analysis (TGA) carried out to clarify thermal stability of the ligand and its complexes. The optical band gap (Eg) was calculated using Tauc's equation and compared with their HOMO‐LUMO gap obtained from DFT quantum chemical calculations. Furthermore, the in vitro cytotoxic activity against Hela (Epitheliod Carcinoma) and WISH (Human amnion) cell lines of isolated compounds were examined. The data indicated that the ligand has very strong activity against Hela cell line and moderate activity against WISH cell line. Accordingly, the metal complexes showed more potent effect against Hela than WISH cell lines. [ABSTRACT FROM AUTHOR]

Herein, the constructing synthon 3‐oxobutanamidothiophene derivatives 2 a and 2 b were synthesized and utilized for building a wide variety of pyran, thiazole, pyrazole or pyrimidine ring heterocyclic compounds that can be used as anticancer medications. 3‐Oxobutanamidothiophene derivatives 2 a,b were coupled with 4‐substitutedphenyl diazonium chloride to produce the corresponding hydrazones derivatives 3 a–f. Various thiophene‐pyran derivatives 4 a,b were synthesized through the treatment of thiophene components 2 a,b with different arylidene‐malononitrile. 2‐Aminothiophene derivatives 5 were prepared via Gewald's reaction between 2 a,b, elemental sulfur, and various activated nitrile derivatives. The 3‐oxobutanamidothiophene derivatives 2 a,b were reacted with PhNCS and the potassium salt intermediates 6 a,b with ethyl bromoacetate to pick up the corresponding thiophene‐thiazolidin‐4‐one derivatives 7. Treatment of the conforming thiocarbamoyl compounds 8 a,b, which undergo heating with three types of α‐halogenated reagents to afford the corresponding substitutedthiophene‐3‐carboxamides 9 a,b. Condensation of keteneN,S‐acetals 10 a,b with hydrazines furnished the thiophene‐pyrazole‐4‐carboxamide hybrids 11 a,b, while condensation with urea and/or thiourea afforded the corresponding thiophene‐pyrimidine‐5‐carboxamides 12 a,b. The recently synthesized thiophene compounds were characterized there in vitro anticancer properties against HepG2 (hepatocellular carcinoma) and MDA‐MB‐231 (breast cancer) were evaluated. Molecular docking was also performed to predict the binding modes of synthesized derivatives with the good anticancer results designed as potential inhibitors for a specific target. [ABSTRACT FROM AUTHOR]

3-Amino-5-bromo-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine (2) was utilized as a precursor for the construction of new polyheterocyclic ring systems. It reacted with 4-substituted arylidene malononitriles and/or ethyl acetoacetate to furnish the corresponding pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidine derivatives 4a–c and 6, respectively. Diazotization of the precursor 2 followed by coupling with ethyl cyanoacetate was the route for the formation of pyrido[2',3':3,4]pyrazolo[5,1-c]triazine derivative 8. The synthesized N-(5-bromo-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-2-cyanoacetamide (10) was utilized for the synthesis of 6-amino-4-aryl-1-(pyrazolo[3,4-b]-pyridin-3-yl)-1,2-dihydropyridines derivatives 12a–c via its treatment with three types of arylidene malononitrile. N-(5-Bromopyrazolo[3,4-b]pyridinyl)-2-(4-oxothiazolidin-2-ylidene)acetamide 13 and N-(5-bromopyrazolo[3,4-b]pyridinyl)-2-cyano-2-(4-oxo-3-phenylthiazolidin-2-ylidene)acetamide 15 were picked up through the reactions of 10 with 2-mercaptoacetic acid and/or Ph-N = C = S with BrCH2COOEt. The tricyclic ring system, 9-bromo-3-cyano-2-oxo-pyrido[2',3':3,4]pyrazolo[1,5-a]-pyrimidine derivative 18, was used as building block for the construction of new tetra- and penta-heterocyclic compounds 19, 20, and 21 through its reaction with some bis-nucleophilic reagents; hydrazine hydrate, malononitrile and 4-(4-anisylazo)-1H-pyrazole-3,5-diamine. The newly synthesized pyrazolo[3,4-b]pyridine-based heterocycles were characterized by the IR and 1H NMR spectral techniques and their in vitro antibacterial properties were evaluated. [ABSTRACT FROM AUTHOR]

The chloroacetamide derivative, 1, was used as a versatile precursor for the synthesis of various types of N‐aryl‐2‐(benzothiazol‐2‐ylthio)acetamide derivatives. The reaction of 1 with 2‐mercaptobenzothiazole followed by condensation reaction of the produced sulfide with phenylhydrazine, 2‐cyanoacetohydrazide, and/or thiosemicarbazide furnished the conforming condensation products, 4, 7, and 10, respectively. Treatment of the phenylhydrazone product, 4, with Vilsmeier formylation reagent (POCl3/DMF) yielded the corresponding 4‐formylpyrazole derivative, 5. The thiosemicarbazone product, 10, was reacted with ethyl bromoacetate to furnish the thiazolin‐4‐one derivative, 11. The substitution reactions of chloroacetamide derivative, 1, with 2‐mercapto‐4,6‐dimethylnicotinonitrile and 6‐amino‐2‐mercaptopyrimidin‐4‐ol, were explored to identify the sulfide products, 14 and 17. Cyclization of 14 into its corresponding thieno[2,3‐b]pyridine compound, 15, was performed using sodium ethoxide. The thiosemicarbazone, 10, and sulfide derivative, 14, were found to be the most potent antibacterial compounds against Escherichia coli and Staphylococcus aureus, exhibiting growth inhibitory activities of 80.8% and 91.7%, respectively. Moreover, the thiosemicarbazone, 10, displayed the most significant antioxidant activity with inhibitory activity of 82.6%, which comes close to the antioxidant activity of L‐ascorbic acid. [ABSTRACT FROM AUTHOR]

A simple synthesis for a series of chloropyridine derivatives incorporating heterocyclic hybrids has been accomplished. The key reaction involving employment of 5‐chloro‐2‐(cyanoacetamido)pyridines 3 in the synthesis of chloropyridinyl‐pyridone, chloropyridinyl‐pyrazole, chloropyridinyl‐thiazole and chloropyridinyl‐thiophene hybrids. The newly synthesized heterocycles were evaluated for their antioxidant and antibacterial activities against Gram‐positive and Gram‐negative bacterial strains. 3‐Amino‐N‐(3,5‐dichloropyridin‐2‐yl)‐1H‐pyrazole‐4‐carboxamide (12 b) was found to be the most potent compound against Escherichia coli and Staphylococcus aureus exhibiting inhibition percent of 92.3 % and 100 %, respectively, when compared to the standard drug ampicillin. Moreover, compound 12 b displayed the most significant antioxidant activity with percent inhibition 87.8 % which is close to the antioxidant activity of ascorbic acid. [ABSTRACT FROM AUTHOR]

The synthesis of various N-aryl 2-chloroacetamides has been described through chloroacetylation of the corresponding aryl amine. The chemical reactivity of N-aryl 2-chloroacetamides is attributed to the easy replacement of its chlorine atom by nucleophiles (namely; oxygen, nitrogen and/or sulfur). Furthermore, this nucleophilic substitution may accompanied by intramolecular cyclization to furnish miscellaneous heterocyclic systems as imidazole, pyrrole, thiazolidine-4-one and thiophene. [ABSTRACT FROM AUTHOR]

Chemical reactivity of amino group that connected with the para position of acetanilide moiety (p-aminoacetanilide) attained more attention in chemistry. In this review article, we report the chemistry of p-aminoacetanilide and its utilization in the synthesis of azo compounds, pyrrole, imidazole, thiazole and various heterocycles of biological importance. [ABSTRACT FROM AUTHOR]

Various sets of thiazole, thiophene, and 2-pyridone ring structures containing a dimethylaniline component were synthesized. Substituted thiazoles 2–3 and thiophenes 5–7 were produced by reacting thiocarbamoyl compound 4 with α-halogenated reagents in different basic conditions. Also, a series of 2-pyridone derivatives 9a–f substituted with dimethylaniline was synthesized through Michael addition of malononitrile to α,β-unsaturated nitrile derivatives 8a–f. The synthesized products were structurally proven by spectroscopic methods such as IR, 1H NMR, 13C NMR, and MS data. Furthermore, the anti-cancer efficacy of the compounds was assessed using the MTT assay on two cell lines: hepatocellular carcinoma (HepG-2) and breast cancer (MDA-MB-231). The results showed the highest growth inhibition for derivatives 2, 6, 7, and 9c, which were further examined for their IC50 values. The IC50 for compound 2 showed equipotent activity (IC50 = 1.2 µM) against the HepG-2 cell line compared to Doxorubicin (IC50 = 1.1 µM). Compounds 2, 6, 7 and 9c showed very good ADME assessments for further drug administration. Moreover, the PASS theoretical prediction for the compounds showed high antimitotic and antineoplastic activities for compounds 2, 6, 7, and 9c, as well as potent inhibition activity for the insulysin enzyme (IDE). Molecular docking stimulations were performed on CDK1/CyclinB1/CKS2 (PDB ID: 4y72) and BPTI (PDB ID: 2ra3). When docked into (PDB ID: 4y72), all of the tested compounds showed considerable inhibition, and the 2-pyridone derivative 9d had the maximum binding affinity (− 8.1223 kcal/mol). While thiophene derivative 6 offered the maximum binding affinity (− 7.5094 kcal/mol) when docked into (PDB ID: 2ra3). [ABSTRACT FROM AUTHOR]

Dye-sensitized solar cells (DSSCs) offer a cost-effective and attractive alternative to traditional solar cells for greenhouse applications. Hydrazonothiazole dyes (MHS-1-4) have been investigated as a viable DSSC technology, with researchers designing dyes that absorb light in the green region, while transmitting light in the red and blue regions, making them the ideal fit for plant growth. Sensitized devices display impressive power conversion efficiency (PCEs) ranging from 6.27 to 8.85%, with MHS-4 DSSCs achieving an 8.85% power conversion efficiency, a short-circuit photocurrent density of 17.90 mA cm−2, and a maximum incident monochromatic photon-to-electron conversion efficiency (IPCE) of 80%. Furthermore, DSSCs based on MHS-4 demonstrate excellent long-term stability, sustaining nearly constant power conversion efficiency after exposure to one-sun illumination for 1000 h. This breakthrough study demonstrates the potential for hydrazonothiazole dyes in DSSCs, marking a significant step forward in the development of cost-effective solar cell technology compatible with plant growth. With MHS-1-4 dyes' ability to effectively convert photoelectric energy throughout the visible range, and even into the near-infrared (NIR) region up to 900 nm, they offer a new benchmark for DSSC technology. • We develop wavelength-selective semi-transparent DSSCs for greenhouse applications using hydrazonothiazole dyes (MHS-1-4). • Structured dyes absorb green light and transmit red and blue light, so they are compatible with plant light absorption. • Sensitized devices showed increased power conversion efficiencies (PCEs) of 6.27–8.85%. • A maximum efficiency of 8.85% was achieved by MHS-4 in the visible and NIR ranges up to 900 nm. [ABSTRACT FROM AUTHOR]

2‐Cyanoacetamido‐thiazole (1) was employed as a key for the construction of 6‐cyano‐7‐oxo‐7H‐thiazolo[3,2‐a]pyrimidine (4) which underwent reaction with hydrazine, malononitrile, ethyl cyanoacetate, and/or various 1,3‐bi‐nuclophilic reagents furnished the corresponding tri‐heterocyclic and tetra‐heterocyclic ring systems 5–12. In addition, the reactions of 1 with various types of arylidene‐malononitriles and/or ethyl 3‐aryl‐2‐cyanoacrylates yielded the corresponding 1‐thiazolyl‐pyridine derivatives 16 and 20, respectively. Furthermore, treatment of the precursor 1 with carbon disulfide and methyl iodide afforded the ketene dithioacetal derivative 21 which cyclized upon heating with hydrazine and/or 2‐aminobenzimidazole into the corresponding derivatives of N‐(thiazol‐2‐yl)‐1H‐pyrazole‐4‐carboxamide 22 and N‐(thiazol‐2‐yl)benzimidazo[1,2‐a]‐pyrimidine‐3‐carboxamide 23. The antibacterial properties of these thiazole‐based heterocycles were examined against panel of two bacterial strains. [ABSTRACT FROM AUTHOR]

The aim of this study involves the synthesis of novel heterocyclic scaffolds containing acetanilide moiety from the readily accessible 2-substituted-2-(4-acetamidophenylhydrazono)-thioacetanilides, which underwent reaction with various alpha-halogenated reagents (namely: bromoacetone, phenacyl bromide, ethyl bromoacetate and chloroacetonitrile) afforded the corresponding thiophene derivatives 5, 7 and 9. All freshly synthesized scaffolds were elucidated by considering the data of both elemental and spectral analyses. The synthesized scaffolds were screened for anti-oxidant activities and showed promising results. [ABSTRACT FROM AUTHOR]

Newly synthesized 1,2,3‐benzotriazine‐4‐one derivatives substituted at position‐3 were characterized by various analytical and spectral techniques. The in vitro antitumor activity was evaluated against three different cell lines (liver cells cancer, colorectal cancer, and breast cancer), where compounds 7b, 15, and 25 showed strong antitumor activity with IC50 ranging from 5.54 to 16.26 μM. In addition, molecular modeling studies using MOE were performed to investigate their binding modes to the C‐Met kinase active site. Docking results demonstrated that all new compounds recognized the active sites of C‐Met kinase and form different types of bonding interactions with key active site amino acid residues. [ABSTRACT FROM AUTHOR]

A series of some novel 4‐(N‐substituted amino)‐acetanilide scaffolds was synthesized through the nucleophilic substitution reactions of the highly versatile N‐(4‐acetamidophenyl)‐2‐chloroacetamide (3) with various types of nucleophilic reagents such as benzothiazole‐2‐thiol, ethyl 2‐mercaptoacetate, 4,6‐dimethyl‐2‐mercapto‐nicotinonitrile, various thiocarbamoyl derivatives, ammonium thiocyanate, 3‐cyano‐4,6‐dimethyl‐5‐arylazopyridin‐2‐ones, and malononitrile. The synthesized 4‐(N‐substituted amino) acetanilide scaffolds were characterized by spectral analyses and assayed in vitro for breast anticancer activity. 2‐(4‐Acetamidophenylaminocarbonyl)‐3‐amino‐thiophenes 11, 13a, and 13b showed the highest cytotoxic activity. [ABSTRACT FROM AUTHOR]

• We have synthesized a new class of carbazole-based cyanoacetanilides (5a-c) and carbazole based-thiazolidine derivatives (7a and 7b). • Through a theoretical approach using density functional theory (DFT) and molecular docking study, we have highlighted various parameters that influence the use of these new compounds as dye-sensitized solar cells (DSSCs) and anticancer agents. • According to the DFT studies, all the structures (5a-c, 7a, and 7b) meet the prerequisite thermodynamic conditions, making them suitable to be employed as sensitizers in TiO 2 -based DSSCs. • Based on the key photovoltaic parameters (ΔG inj. , ΔG reg. and ΔG rec.), compound 7b is the most favorable candidate for sensitizing the DSSC performance. • The new compounds have been studied theoretically using human pancreatic cancer cells (PDB Code-3qkd) to investigate their anticancer activities. • The results suggest that compounds 5a-c, 7a, and 7b can be applied as potential sensitizers for dye-sensitized solar cells in addition to their performance as anticancer agents. We have synthesized a new class of carbazole-based cyanoacetanilides (5a-c) and carbazole based-thiazolidine derivatives (7a and 7b). These compounds were prepared from 9-hexylcarbazole by employing a multistep synthetic strategy and their structural elucidation was confirmed by the combination of standard spectroscopic methods such as FT-IR, 1H NMR, 13C NMR, MS, and UV–Vis spectral data. Through a theoretical approach using density functional theory (DFT) and molecular docking study, we have highlighted various parameters that influence the use of these new compounds as dye-sensitized solar cells (DSSCs) and anticancer agents. According to the DFT studies, all the structures (5a-c, 7a, and 7b) meet the prerequisite thermodynamic conditions, making them suitable to be employed as sensitizers in TiO 2 -based DSSCs. Additionally, the key photovoltaic parameters such as electron injection, regeneration, and recombination driving force (ΔG inj. , ΔG reg. and ΔG rec.) of these compounds were calculated. Based on the computed results of the above factors, compound 7b is the most favorable candidate for sensitizing the DSSC performance. To further confirm these theoretical results, the experimental UV/Vis. spectra for compound 7b showed the broadest absorption range and the lowest energy gab (2.31 eV) with a maximum molar extinction coefficient of 2.29 × 104 M−1 cm−1, which reflects the better performance properties of dye 7b compared to other structures. Furthermore, the new compounds have been studied theoretically using human pancreatic cancer cells (PDB Code-3qkd) to investigate their anticancer activities. Interestingly, the better binding energy provided by the structure 7b in the silico molecular docking approach reveals its greater affinity for the receptor (binding energy: -9.7856 kcal mol−1 and RMSD: 1.66). Overall, the results suggest that compounds 5a-c, 7a, and 7b can be applied as potential sensitizers for dye-sensitized solar cells in addition to their performance as anticancer agents. [Display omitted] [ABSTRACT FROM AUTHOR]

Cyanoacetic acid hydrazide derivatives were utilized as key intermediates for the synthesis of some new 3-amino- and 5-aminopyrazole derivatives. Coupling of N′-phenylsulfonyl-2-cyanoacetohydrazide ( 1) and 1-(2-cyanoacetyl)-4-phenyl thiosemicarbazide ( 4) with different aryl diazonium chlorides afforded the corresponding 5-amino-1-substituted-4-pyrazolin-3-one derivatives 3 and 6, respectively. Treatment of ketene dithioacetal 9 and ketene-N,S-acetal 13 with hydrazine and/or benzenesulfonyl hydrazide furnished the corresponding 3-amino-5-1 H-pyrazole-4-carbohydrazide derivatives 10, 11, and 14. The structures of the new synthesized compounds were elucidated and confirmed by elemental analyses and spectral data. [ABSTRACT FROM AUTHOR]

Synthetic strategy for the synthesis of thiophene 2-carboxamide derivatives substituted with hydroxyl, methyl and amino groups at position-3 was proposed. The strategy includes the cyclization of the precursor ethyl 2-arylazo-3-mercapto-3-(phenylamino)acrylate derivatives, 2-acetyl-2-arylazo-thioacetanilide derivatives and N-aryl-2-cyano-3-mercapto-3-(phenylamino)acrylamide derivatives with N-(4-acetylphenyl)-2-chloroacetamide in alcoholic sodium ethoxide. IR, 1H NMR, and mass spectroscopic analyses were used to characterize the synthesized derivatives. In addition, molecular, electronic properties of the synthesized products were studied by the density functional theory (DFT) where they exhibited close HOMO–LUMO energy gap (ΔEH-L) in which the amino derivatives 7a-c have the highest while the methyl derivatives 5a-c were the lowest. Using the ABTS method, the antioxidant properties of the produced compounds were evaluated, where amino thiophene-2-carboxamide 7a exhibit significant inhibition activity 62.0% compared to ascorbic acid The antibacterial activity against two pathogenic Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two of pathogenic Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) revealed that 7b records the highest activity index compared to ampicillin 83.3, 82.6, 64.0, 86.9%, respectively. Furthermore, the thiophene-2-carboxamide derivatives were docked with five different proteins with the use molecular docking tools and the results explained interactions between amino acid residue of enzyme and compounds. Compounds 3b and 3c showed the highest binding score with 2AS1 protein. [ABSTRACT FROM AUTHOR]

A new series of 2-pyrazolin-1-ylthiazoles 8a-d and 13-16 was synthesized by cyclization of N-thiocarboxamide-2-pyrazoline with different haloketones and 2,3-dichloroquinoxaline. The structures of the new compounds were confirmed by elemental analyses as well as NMR, IR, and mass spectral data. The newly synthesized compounds were evaluated for their antimicrobial activities, and also their minimum inhibitory concentration (MIC) against most of test organisms was performed. Amongst the tested ones, compound 8c displayed excellent antimicrobial activity. [ABSTRACT FROM AUTHOR]

Abstract: New pyrazolyl-1,2,3-triazoles and 1,2,3-triazol-4-yl-pyrazolylthiazoles were synthesized through multi step reactions using 1-tolylyl-4-acetyl-5-methyl-1,2,3-triazole as a precursor. All the newly synthesized compounds were characterized by spectral and elemental analyses. The structure of 11b was evidenced by X-ray crystallographic study. The newly synthesized compounds were evaluated for their antimicrobial activities and also their minimum inhibitory concentration (MIC) against most of test organisms was performed. Amongst the tested compounds 5a, 5c, 11b and 11c displayed excellent antimicrobial activity. [Copyright &y& Elsevier]

The chemistry of thiohydantoins has gained increased interest in both synthetic organic chemistry and biological fields. Many of these compounds exhibit considerable biological activities in various fields. This review covers the literature regarding the synthesis, reactions, and applications of such compounds. [ABSTRACT FROM PUBLISHER]

[Display omitted] • New organic dyes, called BS-1–8, synthesized with D-π-A configuration for dye-sensitized solar cells. • Efficiencies of DSSCs sensitized with BS-1–8 ranged 2.83%-5.01%; co-sensitization with N719 boosted efficiencies to 9.01%. • Co-sensitization of 0.2 mM BS-4 and 0.2 mM N719 achieved highest efficiency of 9.01 % with J sc of 20.07 mA/cm2. • IPCE and EIS analysis gave insights into efficiency boost from co-sensitizing BS-1–8 and N719. • BS-1–8 shows promise for improving dye-sensitized solar cell efficiency. In this research, we synthesized new organic dyes, called BS-1–8, based on acrylamide/2-pyridone for use in dye-sensitized solar cells (DSSCs). These dyes were designed with a D-π-A configuration and underwent molecular engineering to fine-tune their spectral properties and energy levels. Through a comprehensive analysis combining experimental and theoretical approaches, we investigated various aspects of these dyes, including their optical, electrochemical, photovoltaic, geometrical, and electronic features. The newly developed dyes exhibited strong absorption in the UV–visible range, characterized by high molar extinction coefficients. Upon sensitization with BS-1–8, the efficiency of DSSCs ranged from 2.83 % to 5.01 %. Acrylamide-based sensitizers (BS-1–4) achieved efficiencies ranging from 3.82 % to 5.01 %, while 2-pyridone-based sensitizers (BS-5–8) scored between 2.83 % and 3.57 %. Notably, when co-sensitized with N719 at concentrations of 0.2–0.3 mM, the DSSCs showed a significant increase in power conversion efficiencies (PCEs) ranging from 7.85 % to 9.01 %, compared to 7.50 % for DSSCs sensitized with N719 alone. Specifically, the performance of 0.2 mM BS-4 was 20 % better than that of N719. This improvement in PCEs can be attributed to the enhanced Voc (open-circuit voltage) achieved through co-sensitization, highlighting the potential benefits of using sensitizers to develop more efficient DSSCs. The highest achieved PCE was 9.01 %, accompanied by a Jsc (short-circuit current density) of 20.07 mA.cm −2 and a Voc of 0.732 V for the mixed co-sensitizers (0.2 mM BS-4 + 0.2 mM N719). These findings indicate that the combination of co-sensitization is a promising strategy for developing efficient D-π-A-type sensitizers and evaluating DSSC performance. Additionally, the study of incident photon-to-current efficiency (IPCE) and electrochemical impedance spectroscopy (EIS) provided insights into the mechanisms contributing to these improvements. Overall, these results suggest that BS-1–8 sensitizers have significant potential for advancing the development of more efficient DSSCs. [ABSTRACT FROM AUTHOR]

The objective of this study is to synthesize novel heterocyclic scaffolds containing a thiophene moiety using easily accessible acetoacetamide as a key synthon. The reaction of acetoacetamide with diazonium salts resulted in the formation of the corresponding thiophene derivatives 4a–c. Additionally, the reaction of acetoacetamide derivative 3 with malononitrile, ethyl cyanoacetate, or 2‐cyanoacetamide, along with elemental sulfur, under refluxing in dioxane containing triethylamine afforded thiophene‐containing derivatives 5a–c. Furthermore, compound 3 reacted with phenyl isothiocyanate in dry dimethylformamide and K2CO3 to yield compound 7. In situ alkylation of the non‐isolable salt 6 was achieved by the addition of methyl iodide, resulting in the formation of methylthio‐thiophene‐2‐carboxamide 8. Compound 7 was employed with numerous alpha‐halogenated reagents in ethanol, affording thiazole derivative 9 and thiophene derivatives 10a and 10b, respectively. Moreover, compound 8 was reacted with hydrazine to produce the 1H‐pyrazole‐4‐carboxamide derivative 11. Additionally, refluxing acetoacetamide derivative 3 with malononitrile and/or ethyl cyanoacetate in dioxane, in the presence of catalytic amount of triethylamine afforded 4‐imino‐3,7‐dimethyl‐4H‐pyrido[1,2‐a]thieno[3,2‐e]pyrimidin‐9(5H)‐one derivatives 12a and 12b. Furthermore, the reactivity of acetoacetamide derivative 3 with 2‐cyanoacetohydrazide was investigated through refluxing the reactants in dioxane, which subsequently yielded the corresponding cyanoacetamide derivative 13. The chemical identity of the newly synthesized compounds was determined by employing infrared spectroscopy (IR), 1H NMR, and 13C NMR techniques. Newly synthesized heterocycles incorporating thiophenes were evaluated for their antioxidant and antimicrobial potentials. Notably, thiophene scaffolds 5a, 10b, 11, and 13 displayed notable antioxidant and antimicrobial activities. [ABSTRACT FROM AUTHOR]

In this study, we synthesized new series of 5-oxo-2-phenyl-4-(arylsulfamoyl)sulphenyl) hydrazono)-4,5-dihydro-1H-pyrrole-3-carboxylate hybrids 4a-f with the goal of overcoming sulfonamide resistance and identifying novel therapeutic candidates by chemical changes. The chemical structures of the synthesized hybrids were established over the spectroscopic tools. The frontier molecular orbitals configuration and energetic possessions of the synthesized compounds were discovered utilizing DFT/B3LYP/6-311++ G** procedure. The 3D plots of both HOMO and LUMO showed comparable configuration of both HOMO and LUMO led to close values of their energies. Amongst the prepared analogues, the sulfonamide hybrids 4a-f, hybrid 4a presented potent inhibitory towards S. typhimurium with (IZD = 15 mm, MIC = 19.24 µg/mL) and significant inhibition with (IZD = 19 mm, MIC = 11.31 µg/mL) against E.coli in contrast to sulfonamide (Sulfamethoxazole) reference Whereas, hybrid 4d demonstrated potent inhibition with (IZD = 16 mm, MIC = 19.24 µg/mL) against S. typhimurium with enhanced inhibition against E. Coli, Additionally, the generated sulfonamide analogues'' molecular docking was estimated over (PDB: 3TZF and 6CLV) proteins. Analogue 4e had the highest documented binding score as soon as linked to the other analogues. The docking consequences were fitting and addressed with the antibacterial valuation. [ABSTRACT FROM AUTHOR]

Two novel bithienyl fluorobenzamidine derivatives namely, 4-([2,2′:5′,2′′-terthiophen]-5-yl)-2-fluorobenzamidine hydrochloride salt (MA-1615), 5′-(4-amidino-3-fluorophenyl)-[2,2′-bithiophene]-5-carboxamidine dihydrochloride salt (MA-1740) were synthesized, characterized and their corrosion inhibition properties were evaluated by electrochemical methods for carbon steel (C-steel) in 1 M HCl. Experimental investigations revealed that the inhibition effectiveness of the investigated inhibitors (INHs) by the Tafel polarization method followed the order: MA-1740 (96.9%) > MA-1615 (95.6%), demonstrating higher efficiency than inhibitors of similar structure reported in the literature. The investigated bithiophene derivatives exhibit mixed-type corrosion inhibition characteristics by blocking the active sites on the surface of C-steel. EIS study revealed that the INHs behave as interface-type corrosion inhibitors. UV–Visible spectrometric measurements confirmed a complex formation between the Fe2+ cation released during the corrosion reactions and inhibitor molecules. [ABSTRACT FROM AUTHOR]

• The synthesized arylhydrazonal displayed distinctive solvatochromism. • DFT quantum chemical calculations were used to look into the possible tautomeric transformation of the synthesized arylhydrazonal. • The arylhydrazonal has strong antibacterial action against Grammeme-positive and Grammeme-negative bacteria. • The arylhydrazonal exhibits notable anticancer properties against skin and breast cancer cells, with lower toxicity than normal cells. • It works well to stop carbonic anhydrase isozymes IX and XII, and it works even better against CA-XII than the inhibitor acetazolamide (AZA). • Molecular docking stimulation reveals interactions with diverse proteins, revealing different binding energies. Distinctive quinolinyl hydrazonal-based compound was synthesized by an azo-coupling reaction of an enaminonitrile (piperidinylacrylonitrile) with the diazonium salt of 8-aminoquinoline. The synthesized compound was characterized by different spectroscopic methods and displayed distinctive solvatochromism. The possible tautomeric transformation of the arylhydrazonal was studied using DFT quantum chemical calculations revealing that the E→Z tautomerization was a spontaneous exothermic process and its equilibrium constant (K eq) was high with positive power. Thus, the Z-tautomer is more favorable than E-tautomer. This study looks at arylhydrazonal's multiple biological actions, showing its substantial promise in antibacterial, antifungal, anticancer, and enzyme inhibition applications. The arylhydrazonal exhibited concentration-dependent strong antibacterial action against Gram-positive and negative bacteria. Moreover, it showed a comparable concentration-dependent antifungal efficiency against C. albicans and A. fumigatus , and close to fluconazole's potency against A. fumigatus. The arylhydrazonal exhibits significant anticancer action, targeting skin and breast cancer cells, suggesting lesser harm to normal cells. In comparison with acetazolamide (AZA), It inhibited carbonic anhydrase isozymes IX and XII with substantial potency against CA-XII. Molecular docking investigations demonstrated the compound's interactions with proteins such 1D2S, 1AS0, 4WW8, and 5Fl4, revealing different binding energies, RMSD values, and stable configurations via hydrogen bonding and π-H stacking interactions. These results highlight the compound's potential as a therapeutic agent in a variety of clinical applications, calling for more study into its development and clinical usage. [Display omitted] [ABSTRACT FROM AUTHOR]

• Designed and synthesized six new metal-free 2-cyanoacetanilide based organic dyes (SA1-6) for DSSC application. • All the dyes possess the thermodynamic requirements to be used as DSSCs. • The dyes SA4-6 bearing pyridine moiety showed better efficiency than that of dyes SA1-3 with nitro group. • SA1 co-sensitized with HD-2 displayed the best efficiency (η) of (8.02%) with increasing in both V OC (0.68 V) and J SC (20.33 mA/cm2). The design, synthesis and photovoltaic performance of metal-free 2-cyanoacetanilide based organic dyes, SA1-6 have been reported as sensitizers / co-sensitizers in dye sensitized solar cells (DSSCs). All dyes possess the thermodynamic requirements to be applied in DSSCs. The DFT and TD-DFT calculations were completed using Guassian09 package software. The obtained results showed appropriate charge separation between the ground state oxidation potential (GSOP) and excited state oxidation potential (ESOP) levels of the dyes. In addition, there was a good a greement between the theoretical and experimental data. Over co-sensitization, SA1-6 exhibited better efficiency than the main sensitizer HD-2. Among the dyes we synthesized, SA1 displayed improved PCE of 8.02 % with increasing in both V OC value of 0.682 V and J SC value of 20.33 mA/cm2, whereas the DSSC fabricated with dye HD-2 alone showed PCE of 7.49 % with J SC of 19.01 mA/cm2 and V OC of 0.63 V. Finally, Electrochemical impedance spectroscopy measurements, beside electron lifetimes of SA1-6 and HD-2 , were obtained and are in good agreements with the experimental photovoltaic parameters. [ABSTRACT FROM AUTHOR]

This groundbreaking study reveals an unparalleled strategy for significantly enhancing the efficiency of dye-sensitized solar cells by co-sensitizing a pioneering combination of organometallic dyes. By employing two ingeniously engineered co-sensitizers, MO-1 and MO-2 , in tandem with the standard N719 dye, our revolutionary device demonstrated remarkable performance improvements. The power conversion efficiency increased by nearly 50% compared to N719 alone, reaching an exceptional value of 10.96%. MO-2 played a key role in boosting the outputs by expanding the light harvesting and current generation capabilities. Additionally, the unique alignment and geometry of our rationally designed co-sensitizers, optimized using density functional theory, significantly contributed to remarkable efficiency gains. By effectively reducing electron-hole recombination and suppressing dye aggregation, our sensational cocktail co-sensitization approach opens new avenues for photovoltaic utilization. This pioneering dual-dye method paves the way for a new era of next-generation solar energy. [Display omitted] • Novel organic methylfuran-based co-sensitizers demonstrate enhanced light absorption and high molar extinction coefficients. • Co-sensitization with standard N719 dye improves power conversion efficiency up to 10.96% compared to 7.35% for N719 alone. • Insertion of additional furan unit in MO-2 co-sensitizer extends conjugation, facilitating electron delocalization. • Cocktail co-sensitization combining MO-1 , MO-2 and N719 yields synergistic effects, suppressing dye aggregation. • DFT studies elucidate suitable geometry of co-sensitizers, aiding optimization for dye-sensitized solar cells. [ABSTRACT FROM AUTHOR]

The effectiveness of synthesized antipyrinyl‐imidazotriazole and its derivatives as inhibitors for the corrosion of copper alloy in 0.5 M H2SO4 solution was tested using weight loss, electrochemical impedance spectroscopy (EIS) and potentiodyanmic polarization techniques. The generated results confirmed that the tested compounds have strong inhibition efficiencies for the protection of the corrosion of copper alloy in 0.5 M H2SO4. Maximum inhibition efficiencies (IEs) evaluated from electrochemical measurements at inhibitor's concentrations of 0.040 g/L were 85% (5‐(4‐Antipyrinyl)‐3H‐imidazo[1,2‐b][1,2,4]triazole), 60% (6‐Antipyrinyl‐imidazo[2,1‐b]thiazole) and 72% (2‐Antipyrinyl‐7‐ethoxy‐imidazo[2,1‐b]benzothiazole). It was observed that the inhibition efficiency was strongly influenced by the flow rate of the solution and was reduced to 79 (5‐(4‐Antipyrinyl)‐3H‐imidazo[1,2‐b][1,2,4]triazole), 60% (6‐Antipyrinyl‐imidazo[2,1‐b]thiazole), and 44% (2‐Antipyrinyl‐7‐ethoxy‐imidazo[2,1‐b]benzothiazole) at an agitation speed of 400 rpm. EI from weight loss was comparable with those from PDP of mixed‐type inhibition style and EIS of diffusion model. The low inhibition efficiency for 6‐Antipyrinyl‐imidazo[2,1‐b]thiazole was significantly enhanced from 60% to 90% through a synergistic effect of 0.0001 M KI. The Temkin and Frumkin isotherms indicate the physical adsorption of inhibitors on copper surface. Condensed Fukui function calculations reveal a common center for electrophilic attacks in the three molecules: the nitrogen in the bridged pyrrole rings (labeled as N11). [ABSTRACT FROM AUTHOR]

A series of 2-(4-substituted-phenylimino)thiazolidin-4-one compounds was synthesized via heterocyclizing the corresponding N-aryl-2-chloroacetamides with ammonium thiocyanate. Their chemical structures were elucidated based on an extensive analysis of their spectroscopic data, including infrared, ¹H NMR, 13C NMR, and mass analyses. The possible tautomeric forms of synthesized thiazolidine-4-ones were studied. The tautomerization equilibrium parameters, ΔH, ΔG, and Keq were calculated using the DFT/B3LYP methodology, where it has been indicated that the tautomeric form, phenylimino, is more favourable than the phenylamino form. The antibacterial and antioxidant properties of the synthesized thiazolidin-4-ones were investigated. 2-(Chlorophenyl-imino)thiazolidin-4-one displayed potent antibacterial activity against E. coli (88.46%) and S. aureus (91.66%), and highest percent of inhibition (81.8%, ABTS assay). [ABSTRACT FROM AUTHOR]

Medicinal research has focused on the discovery and progress of anticancer drugs. Carbazole and thiazole are organic heterocyclic compounds that are the building blocks for synthetic and natural pharmaceutical compounds. Thus, this research article involves the synthesis of nine carbazole linked thiazolidinone derivatives from the Knoevenagel reaction of 9-ethylcarbazole-3-carbaldehyde with several thiazolidine-5-one and thiazolin-4-one derivatives. The structures of these compounds were confirmed by spectroscopic tools such as IR, 1H and 13C NMR, and mass spectrometry. The MTT assay, using Cisplatin as a reference drug, was used to test the cytotoxicity of the synthesized carbazole-thiazole analogous against three different cell lines: breast cancer (MCF-7), hepatocellular carcinoma (HepG-2), and colon carcinoma (HCT-116). The 3b and 5c molecules were the most effective antitumor drugs against the three cell lines. Compound 3b has IC50 values of (0.0304 ± 0.001, 0.058 ± 0.002 and 0.047 ± 0.002 µM) for HepG-2, MCF-7, and HCT-116, respectively. When examined on HepG-2, MCF-7, and HCT-116 cell lines, the IC50 values revealed by component 5c were (0.048 ± 0.002, 0.086 ± 0.0025 and 0.06 ± 0.007 µM), respectively. [ABSTRACT FROM AUTHOR]

We report on the synthesis and characterization of six novel 2,2′-bithiophene-based organic compounds (3a–c and 5a–c) that are designed to serve as co-sensitizers for dye-sensitized solar cells (DSSCs) based on TiO2. The compounds are linked to various donor and acceptor groups, and we confirm their chemical structures through spectral analyses. Our focus is on enhancing the performance of metal based N3, and the compounds were designed to operate at the nanoscale. We performed absorption and fluorescence emission measurements in dimethylformamide (DMF), where one of our compounds 5a exhibited the longest maximum absorption and maximum emission wavelengths, indicating the significant impact of the para methoxy group as a strong electron-donating group. Our dyes 5a + N3 (η = 7.42%) and 5c + N3 (η = 6.57%) outperformed N3 (η = 6.16%) alone, where the values of short current density (JSC) and open circuit voltage (VOC) for these two systems also improved. We also investigated the charge transfer resistance at the TiO2/dye/electrolyte interface using electrochemical impedance spectroscopy (EIS), which is important in the context of nanotechnology. According to the Nyquist plot, the 5a + N3 cocktail exhibited the lowest recombination rate, resulting in the highest VOC. Our theoretical calculations based on density functional theory (DFT) are also in agreement with the experimental process. These findings suggest that our compounds have great potential as efficient DSSC co-sensitizers. This study provides valuable insights into the design and synthesis of new organic compounds for use as co-sensitizers in DSSCs based on TiO2 and highlights the potential of these compounds for use in efficient solar energy conversion. [ABSTRACT FROM AUTHOR]

• Synthesis of novel triphenylamine-based porphyrins and used as a starting material for the synthesis of different porphyrins. • The main objective of this work was to study the theoretical investigation for dye-sensitized solar cell applications. • Study the effect of electron donors and electron-withdrawing groups on light-harvesting efficiency. In this work, we have synthesized a series of novel porphyrin derivatives, 8, 12, and 16 in high yields. The new porphyrin derivatives are equipped with different aromatic substituents at the peripheral position. The structures of the new compounds were confirmed by elemental and spectral analyses. Among these porphyrin structures, porphyrins 8, 12 , and 16 were molecularly designed and synthesized based on triphenylamine (TPA), as the core donor (D TPA), linked to one, two, or three porphyrin (D Porph) moieties with different numbers of anchoring groups (AG) to generate: D TPA -π-D Porph -A(DE 1), D TPA (π-D Porph -A) 2 (DE 2) and D TPA (π-D Porph -A) 3 (DE 3). The structural, electronic, and spectroscopic properties of the dyes have been obtained by using the density functional theory (DFT) and time-dependent-DFT calculations. Based on the DFT studies, porphyrins 8, 12 , and 16 possess all thermodynamics requirements to be used for DSSCs as the HOMO values for these three porphyrins are greater than the electrolyte's redox potential (I −/I 3 −, -5.2 eV), while the LUMO level more negative than the conduction band of TiO 2 (- 4.2 eV), which indicate that these structures are suitable as sensitizers in DSSCs. All proposed structures were estimated in the gaseous state based on their optimized ground state geometry to estimate their E HOMO , E LUMO , and HOMO-LUMO energy gaps. porphyrins 8, 12 , and 16 electronic excitations were also probed using TD-DFT experiments, which were performed under the impact of time-dependent disturbances. The simulated absorption spectra of these structures revealed the porphyrins' typical Soret- and Q-bands. porphyrin 16 with tri-cyanoacrylic acid anchoring groups has a wider absorption spectrum than other porphyrins (8, 12), and their Soret- and Q-bands are red-shifted. As a final step, we analyzed and described the DSSC's performance using the concept of DFT reactivity indices. A more efficient DSSC can be built using this approach to correlate cell efficiency with molecular properties. Optimized molecular structure of porphyrins 8, 12, and 16. [Display omitted] [ABSTRACT FROM AUTHOR]

A series of new metal-free D–D-π–A dyes (TMS-1-4) based on triphenylamine (TPA) and carbazole (Cz) that work as strong donor species have been made and used in dye-sensitized solar cells (DSSCs). Malononitrile (-MN), cyanoacrylic acid (-CA), nitrophenylacetonitrile (- NAN) and iminophenylcarboxylic acid (-CH) are the four electron-withdrawing entities connected to the electron-rich TPA-Cz unit in this innovative design. Their molecular structures were identified using all required spectral analyses, as well as by investigating their optical and electrochemical properties. Molecular geometries designed using DFT have also been used to understand how the structures of TMS-1-4 affect their photovoltaic capabilities. The dyes exhibited a strong absorption band in the wavelength range (686 nm–730 nm) that can be translated to a strong light harvesting ability. The photovoltaic conversion efficiencies (PCEs) of TMS-1-4 and the reference dye N719 were also studied, and the rankings were as follows: TMS-2 (8.81%) > TMS-4 (8.03%) > N719 (7.60%) > TMS-3 (6.85%) > TMS-1 (6.51%). Furthermore, the behavior of the dyes was studied after using CDCA, which causes an increase in PCE for all dyes due to an increase in short current value. This work suggests that metal-free dyes (TMS-1-4) are promising candidates for improving the DSSC performance. [Display omitted] • We have designed and synthesized new metal-free dyes (TMS-1-4) for dye-sensitized solar cells. • The dyes exhibited a strong absorption band in the wavelength range (686 nm–730 nm). • As a sensitizer, TMS-2 showed the highest power conversion efficiency of 8.81 %. • TMS-2 -based DSSC with 0.5 mM CDCA as the co-adsorbent exhibited the best PCE of 8.89%. [ABSTRACT FROM AUTHOR]

This investigation outlines the synthesis and design of four innovative organic dyes (MRS-1-4) as co-sensitizers for dye-sensitized solar cells (DSSCs), which are co-sensitized with the well-established Ru (II) dye N719. These new dyes incorporate an electron-rich furan unit attached with thiazole as auxiliary acceptors that linked into electron-withdrawing/anchoring groups, such as carboxylic and nitro groups, which enhances the photovoltaic performance of the cells. We conducted a thorough characterization of the co-sensitizers using a variety of techniques and evaluated their photovoltaic performance by analyzing their optical and electrochemical parameters, as well as their molecular geometries derived from density functional theory (DFT) calculations. To increase the efficiency of DSSCs, we co-sensitized the MRS-1-4 dyes with N719 , which led to a significant improvement in the power conversion efficiency (PCE) of the cells. The DSSC fabricated using MRS-4 dye as a co-sensitizer with N719 attained a remarkable PCE of 8.13%, with an impressive short-circuit current density (J SC) of 19.50 mA cm−2, open-circuit voltage (V OC) of 0.65 V, and fill factor (FF) of 64.18%, while the single-DSSC device with N719 e exhibited a PCE of 7.50%, with J SC of 17.99 mA cm−2, V OC of 0.69 V, and FF of 60.42%. In addition, we performed theoretical characterization of the co-sensitizers using time-dependent DFT, which was in excellent agreement with the experimental results. Our findings demonstrate that the MRS-1-4 co-sensitizers are highly promising candidates for the development of efficient DSSCs and provide valuable insights into the design and optimization of co-sensitizers for enhanced photovoltaic performance. • Four innovative organic dyes (MRS-1-4) have been synthesized as co-sensitizers for dye-sensitized solar cells (DSSCs). • Co-sensitizing the MRS-1-4 dyes with N719 significantly improved the power conversion efficiency (PCE) of the cells. • MRS-4 dye leading to a remarkable PCE of 8.13%. • Theoretical characterization using time dependent DFT was in excellent agreement with the experimental results. [ABSTRACT FROM AUTHOR]

p-Fluorophenacyl chloride (1) was used as a building block for the preparation of new tetra-substituted thiophene derivatives. The basic-catalyzed reaction of 1 with various thiocarbamoyl compounds such as 2-acetyl-2-substituted-thioacetanilides 2a,b, 3-arylazo-4-mercapto-4-phenylamino-buten-2-ones 5a–c, ethyl 2-arylazo-3-mercapto-3-phenylamino-acrylates 8a–c, N-aryl-2-cyano-3-mercapto-3-phenylamino-acrylamides 11a–c, N-aryl-2-(mercapto(phenylamino)methylene)-3-oxo-butanamides 14a–c, and 2-mercapto-4,6-dimethylnicotinonitrile 17 led to the production of their corresponding substituted thiophene compounds 4a–b, 7a–c, 10a–c, 13a–c, 16a–c, and 19 in moderate yields. The newly synthesized thiophene compounds were deduced according to FTIR, 1H NMR, 13C NMR, 19F NMR, and mass analyses along with micro-analytical data. The synthesized thiophene compounds were tested to evaluate their antibacterial and antioxidant activities. The majority of the synthesized thiophenes showed good to moderate anti-bacterial and antioxidant activities. The hydroxythiophene compound 4a showed extremely high antibacterial activity with inhibition zones 15–21 mm (from 60 to 87.5% activity indices). It inhibits bacterial growth and approaches the activity of Ampicillin, which inhibits bacteria with areas of inhibition from 23 to 25 mm. The hydroxythiophene compound 4a showed excellent antioxidant properties (85.9%) relative to the reference, Ascorbic acid (88.0%). [ABSTRACT FROM AUTHOR]

N‐(Anisyl)‐5‐(2‐chloroacetamido)‐4‐cyano‐3‐methylthiophene‐2‐carboxamide (3) was synthesized and reacted with several nucleophilic reagents. The reactions with sulfur nucleophiles (namely, mercaptoacetic acid, ethyl 2‐mercaptoacetate, 5‐(phenylamino)‐1,3,4‐thiadiazole‐2‐thiol, 2‐mercapto‐4,6‐dimethyl‐nicotinonitrile, 4‐anilino‐3‐arylazo‐4‐mercapto‐butenones, ethyl 3‐anilino‐2‐arylazo‐3‐mercapto‐acrylates, and ammonium thiocyanate) yielded the corresponding sulfide, thiophene, or thiazolin‐4‐one derivatives, respectively. The reaction with salicylaldehyde (an example of oxygen nucleophile) furnished the targeting benzofuran compound 21. The reactions with nitrogen nucleophiles (namely, piperidine and aniline) yielded the corresponding thiophene‐carboxamide derivatives 23 and 25, respectively. IR, 1H NMR, and 13C NMR were used to deduce the structures of the target thiophene containing compounds. The effect of the synthesized thiophenes on the viability of HepG2, A2780, and A2780CP was determined. The most effective drug was shown by the thienopyridine‐carboxamide compound 11, against liver cancer cell lines (HepG2) and ovarian cancer cell lines (A2780CP and A2780), whose IC50 values were remarkably near those of Sorafenib, the antitumor drug. [ABSTRACT FROM AUTHOR]

The synthesized Zeolite A/ZnCl2 nanoparticles via the hydrothermal route were characterized using FTIR, XRD, and SEM/EDAX techniques. The characterized catalyst was used for the eco-friendly synthesis of 4,5-dihydro-pyrazole-1-carbothioamide derivatives. Under solvent-free conditions, a multi-component reaction between hydrazine, isothiocyanate, and chalcone was done with a prepared nano-catalyst as an inexpensive, recyclable, easy-to-get, and nontoxic catalyst. The molecular docking study explained that dihydro-1-carbothioamide pyrazoles can be considered COVID-19 main protease (Mpro) inhibitors. In order to investigate the 3D conformation of the compounds that were synthesized, the density functional theory (DFT) was applied with a B3LYP hybrid functional and a 6-311++ G(d,p) basis set. This allowed us to investigate the compounds' electronic and charge transfer properties. In this series of compounds, the derivative 30d showed the lowest HOMO-LUMO energy gap. [ABSTRACT FROM AUTHOR]

A series of new thiophene derivatives was prepared through nucleophilic substitution reactions of the precursor N-(4-substituted-phenyl)-5-(2-chloroacetamido)-4-cyano-3-methylthiophene-2-carboxamides 4a and 4b with different sulfur and/or nitrogen nucleophilic reagents (namely; mercaptoacetic acid, 2-mercaptobenzothiazole, 5-(phenylamino)-1,3,4-thiadiazole-2-thiol, 2-mercapto-4,6-dimethylnicotinonitrile, 3-arylazo-4-mercapto-4-(phenylamino)-but-3-en-one derivatives, ammonium thiocyanate, piperidine and/or morpholine). The structures of the prepared thiophene compounds were characterized by spectral analysis. Their cytotoxicity was evaluated against two human cancer cell lines (HepG2 and MCF-7) and indicated promising results. Pretreatment of HepG2 cells with the tested compound 4b sensitized the cells to the cytotoxicity of sorafenib, leading to a significant decrease in the IC50 from 3.9 to 0.5 μM. [ABSTRACT FROM AUTHOR]

Sixteen novel compounds, based on triazole-linked pyrazolines, are synthesized by routine and facile multistep reactions. [ABSTRACT FROM AUTHOR]

A novel series of antipyrinyl thienyl ketones 4a-c, 7a-c, 10a-c, and 13a-b was chemically synthesized through the cyclocondensation of 4-chloroacetylantipyrine with various 2-substituted-thioacetanilide scaffolds, including 3-arylazo-4-mercapto-4-phenylamino-buten-2-ones, ethyl 2-arylazo-3-mercapto-3-phenylamino-acrylate, 2-cyano-3-mercapto-3-(phenylamino)-N-arylacrylamide, 4-mercapto-4-(phenylamino)but- 3-en-2-one, and/or ethyl-3-mercapto-3-(phenylamino)acrylate. Indeed, the reaction of 4-chloroacetylantipyrine with 4-hydroxybenzaldehyde followed by refluxing with 2-cyanoacetohydrazide yielded 2-cyano-N'-(4-(2-(antipyrin-4-yl)-2-oxoethoxy)benzylidene)-acetohydrazide 17 as a building compound, which was used consequentially to synthesize a set of new antipyrinyl thienyl hybrids 19a-d. The chemical structures of newly synthesised compounds were unambiguously confirmed using extensive elemental and spectral data analyses. The newly synthesized compounds were screened for their antioxidant and antimicrobial activities. Compared to the test reference (Ascorbic acid, 88.0%), the antipyrinyl thienyl ketones 13a and 13b substituted with methyl and/or hydroxyl groups at the thiophene ring system displayed excellent antioxidant properties, 87.8% and 87.2%, respectively. Additionally, antipyrinyl thienyl ketones 13a and 13b showed high antibacterial activities, and their relative activity index (which ranges from 68% to 91.7%) was close to that of a reference compound, Ampicillin. [ABSTRACT FROM AUTHOR]

A number of interesting N-(4-chlorophenyl)-2-phenoxyacetamide derivatives were synthesized through interaction of N-(4-chlorophenyl)-2-(4-formylphenoxy)acetamide (1) with cyanoacetamide derivatives 2a-e, hydrazine derivatives, activated nitriles and acetophenone to yield novel acrylamide, hydrazone, acrylonitrile and chalcone derivatives, respectively. Acrylamide derivatives 3a-e were used as precursors for synthesis of 2-pyridone derivatives comprising phenoxyacetamide moiety. The structures of the newly synthesized compounds were avowed by different spectroscopic techniques such as FT-IR, 1H-NMR, 13C-NMR, and mass spectroscopy. Finally, the insecticidal efficacy of the newly synthesized phenoxyacetamide derivatives was tested using the cotton leafworm Spodoptera littoralis. Among all, compounds 12, 6 b and 6c exhibited excellent results. [ABSTRACT FROM AUTHOR]

Review: 96 refs. [ABSTRACT FROM AUTHOR]

A new series of pyridine, thiazole, and pyrazole analogues were synthesized. The pyridone analogues 4a-e were synthesized by treating N-aryl-2-cyano-3-(4-(diphenylamino)phenyl)acrylamides 3a-e with malononitrile. Many 4-arylidene-thiazolidin-5-one analogues 6a-d were obtained by Knoevenagel reactions of 4-(diphenylamino)benzaldehyde (1) with their corresponding thiazolidin-5-one derivatives 5a-d. The structural elucidation of the products was proven by the collections of spectroscopic methods such as IR, 1H NMR, 13C NMR, and MS data. Their anti-cancer activity was examined against two cell lines, MDA-MB-231 (mammary carcinomas) and A-549 (lung cancer). Compared with cisplatin as a reference standard drug, 6-amino-4-(4-(diphenylamino)phenyl)-2-oxo-1-(p-tolyl)-1,2-dihydropyridine-3,5-dicarbonitrile (4b) and 6-amino-4-(4-(diphenylamino)phenyl)-1-(4-nitrophenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile (4e) exhibited better efficiency against the A-549 cell line, with IC50 = 0.00803 and 0.0095 μM, respectively. Also, these compounds 4b and 4e showed the most potency among the examined compounds against MDA-MB-231 with IC50 = 0.0103 and 0.0147 μM, respectively. The newly synthesized compounds were docked inside the active sites of the selected proteins and were found to demonstrate proper binding. 2-Cyano-2-(4,4-(diphenylamino)benzylidene)-5-oxo-3-phenylthiazolidin-2-ylidene)-N-(p-tolyl)acetamide (6c) offered the highest binding affinity (− 8.1868 kcal/mol) when docked into (PDB ID:2ITO), in addition to 2-cyano-N-(4-(diethylamino)phenyl)-2-(4-(4-(diphenylamino)benzylidene)-5-oxo-3-phenylthiazolidin-2-ylidene)acetamide (6a) gave the highest energy score (− 9.3507 kcal/mol) with (PDB ID:2A4L). [ABSTRACT FROM AUTHOR]

In this study, we describe the synthesis and characterization of three newly developed metal-free organic dyes, denoted as MRS-1-3. These dyes have been specifically designed and investigated as potential sensitizers for Dye sensitized solar cells (DSSCs). The sensitizers under consideration consist of pyrene units that function as effective electron donors, whereas furan moieties serve as π-spacers. MRS-1-3 was synthesized by including electron acceptor groups, such as cyanonitroacetonitrile, 4-nitrocyanoacetamide, and dicyanovinyl. In this study, a thorough examination was conducted to assess the individual performances of several sensitizers. The results revealed that MRS-3 , characterized by a furan π-bridge and dicyanovinyl acceptor group, had the best power conversion efficiency (PCE) of 8.77%. This PCE value surpassed that of N-719 , which was determined to be 7.37 %. To enhance the efficacy of MRS-3 , an investigation was conducted to assess the impact of co-adsorption using an unidentified co-adsorbent, chenodeoxycholic acid (CDCA), and to compare its performance with that of 2-(p -carboxybenzylidene)-2-cyano-p-(diethylamino)acetanilide (SA-10) synthesized in a previous study. Notably, MRS-3 's power conversion efficiency (PCE) went up significantly after co-adsorption with CDCA, reaching 8.83%. Furthermore, the substitution of CDCA with the co-adsorbent SA-10 resulted in enhanced performance of the MRS-3 organic dyes in terms of key parameters such as Jsc (short-circuit current density), Voc (open-circuit voltage), and PCE (Jsc = 21.50 mA cm−2, Voc = 0.750 e V; PCE = 10.15 %). A system composed of MRS-3 and SA-10 exhibits exceptional performance, making it a suitable option for creating highly effective DSSCs. The results of this study provide a valuable contribution to the development of new sensitizers that can be used in future photovoltaic applications. These findings present excellent prospects for improving the efficiencies of solar cells. [Display omitted] • Novel organic sensitizer MRS-1-3 as sensitizer comparing with Ru-based N719 dyes in DSSCs. • MRS-3 exploits the ability of dicyanovinyl group to bind acids on TiO 2 , reducing dye competition and increasing voltage. • Co-sensitized device with SA-10 + MRS-3 demonstrated highest efficiency of 10.15 %. • Compatible co-sensitizers at optimal concentrations provide insights into improving DSSC performance. [ABSTRACT FROM AUTHOR]

A new series of thiophene-based organic chromophores (4–7 a, b) has been developed through structural engineering of the electron donor (D) group, incorporating N,N -dimethylaminophenyl and morpholinophenyl, and acceptor moieties such as benzonitrile and flurobenzonitrile. Additionally, a π-linkage of phenylthiophene was inserted. The effects of various donating and accepting groups, as well as the spacer, on the geometrical, energetic, absorption, and photovoltaic properties of these sensitizers were investigated using Density Functional Theory (DFT) and Time-Dependent DFT. The sensitizers were optimized in their ground state using selected functional methods. Furthermore, key properties such as absorbance, frequency, energies of Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO), energy gap, dipole moment, and global reactivity descriptors were calculated using quantum chemical calculations. These spectral properties and quantum chemical calculations provide valuable insights into the potential use of these sensitizers in photonic devices. The results obtained from analyzing light harvesting efficiency (LHE), free energy injection (ΔG inj), and open circuit voltage (Voc) demonstrate that these dyes show promising characteristics for future experimental studies and offer guidelines for improving the performance of dye-sensitized solar cells. By employing structural modifications and investigating the electronic properties of these newly developed chromophores, this study contributes to the understanding of their behavior and potential applications in photonic devices. The findings provide a foundation for further experimental investigations and offer valuable insights for the development of more efficient dye-sensitized solar cells. • Novel thiophene-based organic dyes with different donors and acceptors were designed computationally. • Dyes were synthesized experimentally and characterized by spectroscopic techniques. • Density functional theory calculations analyzed geometric, optical and photovoltaic properties of the dyes. • Dye with N,N-dimethylaminophenyl donor and fluorobenzonitrile acceptor showed promising performance. • Computational insights guide design of efficient organic photosensitizers for solar energy conversion. [ABSTRACT FROM AUTHOR]