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This review article includes the methods for the preparation of 2-cyanomethylbenzothiazole, its chemical reactivity towards different electrophiles and nucleophiles, and its use for the synthesis of heterocyclic compounds. Its biological activity and applications are also reported. This review includes 159 references. [ABSTRACT FROM AUTHOR]

This review presents a systematic and comprehensive survey of the methods of preparation and the chemical reactivity of cyanoacetamide derivatives. These compounds are important intermediates for the synthesis of a variety of otherwise difficult to obtain synthetically useful and novel heterocyclic systems. [ABSTRACT FROM AUTHOR]

In this work, the dipyrromethane derivatives 2a,b were synthesized from an aldehyde and excess of pyrrole at room temperature in solvent-free conditions. The reaction of dipyrromethanes 2a,b with different aromatic aldehydes in the presence of hydrochloric acid or p-toluenesulfonic acid as a catalyst afforded some new porphyrin like and A 2 B 2 porphyrin derivatives 4a-g and 5a-d, respectively. Biological evaluation of the newly synthesized compounds 4a-g and 5a-d showed promising activity as antimicrobial and antioxidant agents. Compounds 4c,4e,4g,5c, and 5d exhibited the highest antimicrobial activity, whereas, compounds 4a,4f,5a,5b, and 5d recorded the highest antioxidant activity. • Our work aimed to synthesize unsymmetrical A 2 B 2 porphyrins and porphyrin like. • New dipyromethanes were synthesized in solvent freeconditions. • Compounds 4c,4e,4g, 5c and 5d have been exhibited higher antimicrobial activity, whereas compounds 4a,4f,5a,5b, 4d and 5d have been recorded higher antioxidant activity. [ABSTRACT FROM AUTHOR]

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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]

Various benzothiazole derivatives were synthesized by allowing 2-cyanomethylbenzothiazole (1) or its arylidene derivatives to react with diverse reagents under different simple and efficient reaction conditions. The chemical structures of novel synthesized benzothiazole derivatives were affirmed by elemental analysis and different spectral data. The newly synthesized compounds were assessed as antibacterial agents against Staphylococcus aureus and Escherichia coli bacteria. [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]

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]

• Synthesis of new cyanoacetamidopyrimidine compounds and their utility as a starting material for the synthesis of more heterocyclic compounds bearing pyrimidine moiety. • The main objective of this work was to study cytotoxicity and antitumor evaluation of the new pyrimidine derivatives. • Study the structure-activity relationship (SAR) of the newly prepared pyrimidine derivatives. • Study the molecular docking of the newly prepared pyrimidine derivatives. The precursor cyanoacetamide derivatives (6) were achieved by the reaction of pyrimidine derivative 5 with cyanoacetic acid catalyzed by acetic anhydride. The reaction of cyanoacetamide derivative 6 with different reagents afforded many heterocyclic systems such as thioacetic acid (9) , dithiolane derivatives (11) and (12) , 1,8-naphthyridine (14) , quinoline derivatives (17) and (18) , pyridine derivatives 20, 22, 24, 26 , and 27 , pyridazine (30) , pyranopyrimidine (32) , and pyrazolopyrimidine (34). All the newly synthesized compounds were characterized with spectroscopic analyses. Compounds were tested for their anticancer activity against three human cancer cell lines: hepatocellular carcinoma (HepG-2), colon cancer (HCT-116), and mammary gland breast cancer (MCF-7). The studied compound's cytotoxic activity ranged from very strong to very weak. The most active compounds were 9, 10, 11, 27 , and 34. The binding disposition of the docked compounds, in particular 9, 10, 11, 27, and 34 , towards the binding site of AKT complexed with co-crystallized ligand was investigated using molecular docking (PDB = 4EJN). A new approach for the synthesis of some new heterocyclic compounds bearing pyrimidine rings as antitumor agents. [Display omitted] [ABSTRACT FROM AUTHOR]

Review: [135 refs. [ABSTRACT FROM AUTHOR]

Herein, we report the design and synthesis of two metal-free organic sensitizers ( MR-5 & MR-6 ) with a D-π-A-π-A architecture based on a trimethoxy benzene donor core carrying two different withdrawing/anchoring groups including cyanoacetic acid and rhodanine-3-acetic acid via thiophene as a π-spacer. Benzothiadiazole was incorporated as a strong auxiliary electron acceptor, which greatly improved the molar extinction coefficient and electronic coupling across the molecular diameter of the dyes. The optical and electrochemical properties of the two dyes were investigated. The photovoltaic studies revealed that MR-5 anchored with cyanoacetic acid showed significantly greater light harvesting (IPCE), which resulted in improved PCE with better photovoltaic parameters than MR-6 . MR-5 achieved the higher total solar-to-electric conversion efficiency of 6.03% and showed an IPCE of 65% at 420 nm. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations were used to study equilibrium molecular geometries, frontier molecular orbitals, vertical electronic excitations, and the theoretical data were consistent with experimental results. [ABSTRACT FROM AUTHOR]

Two novel ruthenium complexes, MR-1 and MR-2 were synthesized for use in dye-sensitized solar cells (DSSCs). Under similar fabrication conditions, the photovoltaic performances of these dyes were evaluated and compared to the standard ruthenium complex N719. MR-1 and MR-2 showed the efficiencies of 8.19% and 5.32%, respectively, while N719 achieved 7.66%. MR-1 also displayed higher V OC than MR-2, which is due to the larger molecular size and higher molar extinction coefficient of the former, which translates into less dye aggregation on a thinner film of TiO 2 . Incorporation of terthiophene as a linker reduces the band gap of MR-1 when compared to that of MR-2. The influence of π-conjugated bridge on optical and electrochemical properties was investigated. Results demonstrated that the absorption band of MR-1 displayed higher extinction coefficient with a broader absorption compared to MR-2 and the benchmark Ru(II) dye, N719, due to the enhancement of electron donating ability of π-conjugated bridge. [ABSTRACT FROM AUTHOR]

In this work, we studied the photovoltaic performance of two novel metal-free organic dyes (MR-3 and MR-4) with the molecular motif D–π–π–A carrying the same donor (trimethoxy benzene) and terthiophene (π) units but with different anchoring moieties. MR-3 and MR-4 displayed PCE of 4.54% and 2.38%, respectively. Furthermore, MR-3 co-sensitized with NCSU-10 exhibited improved efficiency of 9.09% than NCSU alone (8.74%). One of the merits in the studied structure motif D–π–π–A was modulating the molecular geometry of the sensitizers and eliminating the steric effect between the donor and π-spacer (terthiophene) to furnish a coplanar molecular structure and to maximize electronic conjugation. In addition, coupling-steric effect precludes effective conjugation and reduces light harvesting as it increases the band gap. To eliminate the steric effect of the aryl moiety at ortho position of 2,4,6-trimethoxyphenyl donor, another conjugated spacer, alkene (CH=CH), was inserted between the donor and the π-spacer (terthiophene), which maximized the electron conjugation throughout the coplanar system; the optimized molecular geometry of the dyes was calculated using DFT. Another molecular geometry feature that was studied was the influence of different anchoring groups on coplanarity of the dye structure and consequently the photovoltaic performance. In the case of MR-3, where the anchoring group is based on the cyanoacrylic group, the optimized geometry was found coplanar. However, when rhodanine moiety was used as an anchoring group, the calculated optimized geometry of the dye (MR-4) was not coplanar, which resulted in weak electronic coupling and inferior electronic injection into TiO2 conduction band edge. The inter-relationship between the optimized geometry of the dyes and their photovoltaic performance is discussed. [ABSTRACT FROM AUTHOR]

This exciting study introduces five cutting-edge bithienylnicotinonitrile-based organic dyes (coded GA-1-5) that were specifically synthesized for use in dye-sensitized solar cells (DSSCs). These dyes boast a D-π-A framework and were designed to manipulate spectral properties and energy levels. The researchers conducted a comprehensive analysis of their optical, electrochemical, photovoltaic, geometrical, and electronic characteristics using both experimental and theoretical methods. The dyes exhibited intense UV–vis absorption with high molar extinction coefficients, making them ideal co-sensitizers for ruthenium-based DSSCs. When tested, the co-sensitized devices demonstrated significantly improved power conversion efficiencies (PCEs) ranging from 6.22% to 9.12%, thanks to their enhanced short-circuit photocurrents (J sc), which surpassed those of DSSCs sensitized with N3 alone (PCE = 6.20%). Additionally, GA-1-5 compensated for the photocurrent loss caused by I−/I 3 in co-sensitization, further improving the J sc. We also carried out various spectral and electrochemical characterizations to gain a better understanding of the underlying mechanisms. These findings represent a significant advancement in the field of solar cell technology, paving the way for more efficient and sustainable energy solutions. [Display omitted] • Revolutionary bithienylnicotinonitrile-based organic dyes designed for DSSCs with D-π-A framework. • Comprehensive analysis of optical, electrochemical, photovoltaic, geometrical, and electronic characteristics. • Intense UV–vis absorption with high molar extinction coefficients ideal for co-sensitizing ruthenium-based DSSCs. • Co-sensitized devices exhibit significantly improved PCEs, ranging from 6.22% to 9.12%. • GA-1-5 enhances short-circuit photocurrents, paving the way for sustainable energy solutions. [ABSTRACT FROM AUTHOR]

The reaction of N‐(4‐(phenyldiazenyl) phenyl) carbonohydrazonoyl dicyanide (2) with N‐methyl glucamine afforded 3‐amino‐3‐(methyl (2,3,4,5,6‐pentahydroxyhexyl)amino)‐2‐((4‐(phenyldiazenyl)phenyl)diazenyl)acrylonitrile (3). Additionally, compound 2 produced the pyrazole derivatives 4 and 6, respectively, by reactions with hydrazine hydrate and malononitrile. Moreover, when enaminonitrile 3 was treated with malononitrile, N,N‐Dimethylformamide ‐ dimethyl acetal, and thiourea, it generated the glucaminoid derivatives 9, 10, and 13, respectively. In pyridine, compound 19 was obtained when enaminonitrile 3 interacted with the carbon disulfide. While in sodium hydroxide in N,N‐Dimethylformamide, instead of pyridine, it afforded the methyl carbamodithioate 23. Finally, pyrimidinethione derivative 26 was produced when the enaminonitrile 3 and phenyl isothiocyanate interacted. All new compounds were well established by both spectral and elemental analyses. The antitumor activities were evaluated by testing their impact on the viability of four different cell lines: HepG2 (human hepatocellular liver carcinoma), WI‐38 (human lung fibroblast), VERO (African green monkey kidney epithelial), and MCF‐7 (human breast adenocarcinoma). The antitumor study showed that compound 23 has very strong antitumor activity against the HEPG‐2 cell line. The synthesized compounds were analyzed by docking studies that showed good binding scores against the diverse amino acids of the selected proteins B‐Cell Leukemia/Lymphoma‐2 (Bcl‐2). The conducted docking studies were found to be consistent with cytotoxic results. [ABSTRACT FROM AUTHOR]

In our research, we produced some novel porphyrin derivatives 4a–g in high yields. We also synthesized and characterized some of their metalloporphyrin complexes 5–11. The structures of these novel porphyrins were assured by spectroscopic techniques. The geometric structure and magnetic properties of metallo-porphyrins 5–11 have also been studied. Antiviral and antitumor activities were estimated and the structures activity relationships were accomplished. The Porphyrin derivatives 4g, 4f, 9, 10 and 11 displayed strong antiviral activity for HSV-1 compared to Aphidicoline as reference. While derivatives 4g and 6 exhibited very strong activity against HIV-1. Porphyrin derivatives 4g, 6, 9, and 10, in general, displayed strong activity against all the tested human cell lines. [ABSTRACT FROM AUTHOR]

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 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]

Abstract: In continuation of our efforts to find a new class of antimicrobial agents, a series of 4-hetarylpyrazoles and furo[2,3-c]pyrazoles were prepared via the reaction of 2-chloro-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)ethanone (1) with an appropriate nucleophilic reagents. These compounds were screened for their antibacterial activity against Gram-positive bacteria (Bacillus subtilis and Bacillus thuringiensis), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) and antifungal activity against Fusarium oxysporum and Botrytis fabae. Among the synthesized compounds, 1-(5-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazole-4-yl)-2-methylfuran-3-yl)ethanone (12) showed equal activity with chloramphenicol against B. subtilis (MIC 3.125 μg/mL), while its activity was 50% lower than of chloramphenicol against B. thuringiensis. N-[(4Z)-3-Methyl-1-phenyl-1H-furo[2,3-c]pyrazol-4(5H)-ylidene]-1H-benzimidazol-2-amine (7) and 2-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-4H-furo[3,2-c]chromen-4-one (13) were found to exhibit the most potent in vitro antifungal activity with MICs (6.25 μg/mL) against B. fabae and F. oxysporum. [Copyright &y& Elsevier]

The versatile, hitherto unreported 2-cyano-3-(dimethylamino)-N-(4-phenylthiazol-2-yl)- acrylamide 2 was synthesized and allowed to react with hydroxylamine, hydrazine and guanidine to afford regioselectively the isoxazole 4, pyrazole 6 and pyrimidine 8 derivatives, respectively. The reaction of 2 with thiourea and / or ethyl glycinate in a basic medium afforded the regioisomeric pyrimidinethione 9 and 3,5-dioxo-1,4-diazepine-6-carbonitrile 14. Compound 2 reacts also with 2-amino-4-phenylthiazole, 2-amino-4-methylpyridine, 2-aminotetrazole, 2-aminobenzothiazole and 2-aminobenzimidazole to give the corresponding bridgehead nitrogen heterocycles namely thiazolo[3,2-a]pyrimidine 18, tetrazolo[1,5-a]pyrimidine 19, pyrimido [2,1-b]benzothiazole 21, and pyrido[1,2-a]benzimidazole 23. The mechanistic aspects for the formation of the newly synthesized compounds is discussed. [ABSTRACT FROM AUTHOR]

Four novels (N -benzothiazolyl)-cyanoacetamide-based metal-free dyes SA17–20 with D-π-A architecture were designed and synthesized as co-sensitizers for HD-2 for dye-sensitized solar cells (DSSCs). They contain strong donating moieties of trimethoxybenzene and N , N -dimethylaniline conjugated with the nitrile function of cyanoacetamide part (NHCOCH 2 CN) as an anchoring group. The role of donor/acceptor in the cyanoacetamide-based structure motifs of SA17–20 in the co-adsorption properties was characterized and their influence on the optical and electrochemical properties was discussed. Consistent with the experimental results, the equilibrium molecular geometries calculated using density functional theory (DFT), at the B3LYP/ 6–31 G (d, p) level, demonstrated the effect of (N -benzothiazolyl)-cyanoacetamide structures on the photovoltaic performance. Co-sensitization technique mainly depends on the uniqueness of the donor-acceptor unit of the co-sensitizer being used. Using (N -benzothiazolyl)-cyanoacetamide co-sensitizers with HD-2 showed improved power conversion efficiency (PCE) than HD-2 alone. HD-2 was used because of its high efficiency, molar extinction coefficient and photocurrent densities. While HD-2 sensitizer alone displayed PCE of (7.46%), among the co-sensitizers, SA20 , containing methoxythiazole and trimethoxybenzene as a donor part attached to (CN) and (CO) as anchoring components, exhibited the best PCE of (8.27%) with Jsc (19.25 mA/cm2) and Voc (0.68 V). These results demonstrated that (N -benzothiazolyl)-cyanoacetamide dyes SA17–20 are promising candidates for efficient DSSCs. [Display omitted] [ABSTRACT FROM AUTHOR]

Innovative multiple heterocyclic rings incorporating phenothiazine moiety (2–16) were synthesized through the reaction of N-cyanoacetamide phenothiazine derivative (2) with various types of reagents. The new compounds were tested against their antimicrobial activity. Compounds 10, 14, 15 and 16 showed higher activity toward Gram (+) than Gram (−) bacteria strains. Spectral and analytical data confirmed the correct structures of all the compounds. [ABSTRACT FROM AUTHOR]

[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 present work demonstrates the utility of enamines as building blocks for the synthesis of pyrazoles and pyrimidines through efficient procedures. Thus, the reactivity of pyrimidinone‐based enamines 1 a,b towards carbon nucleophiles such as acetylacetone, malononitrile and ethyl cyanoacetate to produce various 1,3‐difunctionalized products has been investigated. Accordingly, a series of new pyrazoles and pyrimidines based on pyrimidinone were prepared and characterized by a variety of synthetic routes through the reactions of 1,3‐difunctionalized products with hydrazine hydrate, urea and guanidine hydrochloride. In vitro biological studies such as cytotoxicity, antioxidant and bleomycin‐dependent DNA damage were screened. Compounds 3 b, 4 b, 7 a‐9 b and 13 a,b displayed wonderful and distinctive activities against the cancer cell line (HepG2), accompanied by mild effects on non‐tumorigenic cells (WI‐38). The antioxidant behaviour of compounds 7 a, 8 a, 9 a, 11 a and 13 a,b has shown a free radical scavenging activity close or superior to vitamin C (reference drug), using the ABTS method. Moreover, the most potent cytotoxic and antioxidant compounds have been demonstrated the pre‐eminent protective impact to DNA against the damage caused by bleomycin. [ABSTRACT FROM AUTHOR]

In this work, enaminones 1 a,b were used as precursors for the synthesis of novel fused heterocyclic ring systems (e. g. pyrazolo[3,4‐d]pyrimidinones, isoxazolo[5,4‐d]pyrimidinones, pyrimido[4,5‐d]pyrimidinones and related compounds) via their reactions with some N‐nucleophiles. The cytotoxic activity of the designed products was assessed via the MTT colorimetric assay against human liver hepatocellular carcinoma (HepG2) and normal lung fibroblasts (WI‐38) cell lines using doxorubicin as a reference standard. Among the screened compounds, pyrazolo[3,4‐d]pyrimidinone 3 d and pyrimido[4,5‐d]pyrimidinones 6 a,b, 7 b and 8 a,b were selected as lead molecules because they showed significant activity against HepG2 cells and a weak cytotoxic effect against WI‐38 cells. In further, all of the compounds were subjected to the bleomycin‐dependent DNA damage studies. The results indicated that most of them have a remarkable ability to protect DNA compared to ascorbic acid as a standard compound. [ABSTRACT FROM AUTHOR]

The photophysical and electrochemical properties of new targeted 2-cyanoacetanilide-based dyes are illustrated. New cyanoacetanilides SA7–10 were synthesized and employed as co-sensitizers in DSSCs. The chemical structures of these 2-cyanoacetanilides differ according to the substituent at the benzene ring (–H, –Me, –OMe and –NEt2), with the anchoring moiety being the same, a –COOH group. Furthermore, a density functional theory (DFT) calculation has shown an effective intermolecular charge transfer character, the HOMOs of SA7–10 are mainly located on the corresponding donor part, and their LUMOs are located on carboxylic acid moieties as the acceptor. Interestingly, using photosensitizers SA7–10 as co-sensitizers with HD-2 dye causes an improvement in their photovoltaic performances. Among the dyes, SA10 co-sensitized with HD-2 displayed an overall efficiency of 8.25%, a JSC of 19.5 mA cm−2, a VOC of 0.65 V and an FF of 64.35 compared to 7.46%, 19 mA cm−2, 0.64 V and 60.54, respectively, of HD-2 only. Moreover, the electrochemical impedance spectroscopy (EIS) data of SA7–10 and HD-2 were found to be in accordance with the obtained photovoltaic parameters. Finally, the results indicated that 2-cyanoacetanilide-based dyes were utilized as promising co-sensitizers due to their easy preparation methods and their relatively small size. [ABSTRACT FROM AUTHOR]

5‐Hydrazineyl‐3‐methyl‐1H‐pyrazole (1) was used as a starting material for the synthesis of novel pyrazolo[3,4‐c][1,2]diazepine derivatives 3, 4, and 6a,b by its reaction with acetylacetone, ethyl acetoacetate, and isatylidene derivatives 5a,b, respectively. Also, pyrazolo[3,4‐c][1,2]diazepine derivative 11 was synthesized via multicomponent reaction of 1, benzaldehyde, and malononitrile. Moreover, compound 1 was used for synthesis novel pyrazolo[3,4‐c]pyrazole derivative 7 by its reaction with isatin. In addition, pyrazolo[3,4‐c]pyrazole derivatives 18a–c were synthesized by treatment of 2‐cyano‐N′‐(3‐methyl‐1H‐pyrazol‐5‐yl)acetohydrazide (13) with aromatic aldehydes 16a–c. The newly synthesized compounds were valeted by means of analytical and spectral data. All newly synthesized compounds were screened for their antioxidant activities. Compounds 3, 13, 18b, and 18c showed higher radical‐scavenging activities. [ABSTRACT FROM AUTHOR]

Reaction of isonicotinaldehyde with 2-cyanoacetohydrazide afforded (E)-2-cyano-N'-(pyridin-4-ylmethylene)acetohydrazide (1). Compound 1 was used as the precursor for the synthesis of novel pyridine derivatives by reaction with different arylidene malononitriles, malononitrile and acetylacetone to give pyridine derivatives 5a-;e, 6 and 7, respectively. 4,4'-Bipyridine derivatives 9a-;d were synthesized by a three-component reaction of isonicotinaldehyde, 2-cyanoacetohydrazide and activated nitriles 8a-;d. Treatment of compound 9a with different aromatic aldehydes gave [1,2,4] triazolo[1,5-a]pyridine derivatives 11a-;c. All reaction products were characterized by analytical and spectral data. For the novel compounds their bioactivity as antitumor agents was examined for in vitro cytotoxicity against HepG-2 and MCF-7. It was found that compounds 9a and 9b have high cytotoxic activity against both HepG-2 and MCF-7. [ABSTRACT FROM AUTHOR]

The present review provides a survey on the structural features, synthetic methodologies, and reactions of phenyl sulfonylacetophenone, considered to be one of the most important synthons in the field of synthetic organic chemistry. β-Ketosulfone is an active C-H acid which has been widely used as a nucleophile in many organic transformations. It has been used for synthesis of five- and six-membered ring systems containing one or two heteroatoms. In addition, it has been used as a starting material for synthesis of fused heterocycles, cyclopropane, cyclopentene, and cyclohexanone derivatives. β-Ketosulfone has been used for synthesis of γ- and δ-ketosulfones, 1,4-diketones, amides, ethers, and substituted benzene derivatives due to its high synthetic importance. It is a reactive intermediate in electrophilic reactions such as halogenation, alkylation, arylation, heteroarylation, and coupling reactions, and is involved in other types of reaction such as Diels-Alder condensation with aldehydes and desulfonylation. The mechanistic pathways of these reactions and their important synthetic applications are discussed herein. [ABSTRACT FROM AUTHOR]

Diazocoupling reaction of curcumin with different diazonium salts of p-toluidine, 2-aminopyridine, and 4-aminoantipyrine in pyridine yielded the arylhydrazones 2a-c. Arylhydrazone of p-toluidine reacted with urea, thiourea, and guanidine nitrate to produce 5,6-dihydropyrimidines. Further reaction of 2a with 2,3-diaminopyrdine in sodium ethoxide solution yielded 1H-pyrido[2,3-b][1,4]diazepine derivative. Bis(2,5-dihydroisoxazole) is obtained from the reaction of 2a with hydroxylamine hydrochloride, while its reactions with hydrazines afforded the respective 4,5-dihydro-1H-pyrazoles. The target compounds were evaluated as antioxidant and antibacterial agents. The tested compounds showed good to moderate activities compared to ascorbic acid and chloramphenicol, respectively [ABSTRACT FROM AUTHOR]

[Display omitted] • Highlights for publication in Journal of Photochemistry and Photobiology A: Chemistry. • Four carbazole organic dyes (MES1-4) with a D-π-A architecture were synthesized for dye-sensitized solar cells. • The study of the dihedral angle and the NBO studies showed that ICT works well within the structure of MES1-4. • Using MES1-4 as sensitizers results in a higher photovoltaic efficiency with a range of 6.06–9.55%. • The MES4 has the highest light harvesting ability owing to the existence of distinct anchoring groups. • The PCE of the DSSC based on MES4 yields a promising PCE of 9.55% and a score that is 32% higher than that of the N719. Synthesis of metal-free organic sensitizers is a promising route for obtaining low-cost, high-efficiency sensitizers for dye-sensitized solar cells (DSSCs). We present the results of a comprehensive photovoltaic analysis of four carbazole organic sensitizers with a D-A architecture in this study. MES 1 - 4 have been developed and used as sensitizers in DSSC applications. Using MES1-4 as sensitizers results in a broader light-harvesting ability (400–800 nm) and higher photovoltaic efficiency at a range of 6.06–9.55 %. Herein, the introduction of thiazolidine-4-one ring engineering into MES4 as a rich electron acceptor enhanced electron injection and inhibited electron recombination in thiazolidine-4-one sensitizers. The MES4 system has the highest light harvesting ability and reflectivity owing to the existence of distinct functional groups that enhanced the capacity to bind the dye with the semiconductor layer (TiO 2 device's efficiency). In conclusion, the DSSC using the novel electron acceptor thiazolidine-4-one ring sensitizer achieves an unexpected PCE of 9.55 % and a 32 % increase over using the N719 metal complex dye. All sensitizers based on carbazole compounds had good photovoltaic performance. [ABSTRACT FROM AUTHOR]

Synthesis and investigation of new donor-acceptor conjugated N-(5-arylazothiazol-2-yl)-2-aminothiophene derivatives with the aim to elucidate the contribution of their interaction with solvent molecules upon intramolecular charge transfer for their potential solar cells application is reported. The UV-visible and emission spectra measurements indicated that the properties of the synthesized dyes had a significant effect on the visible absorption and emission maxima. The effect of the donor and acceptor groups were studied for the nonlinearity based on their HOMO-LUMO band gap energy. The dye-sensitized solar cells (DSSCs) were assembled by using the newly synthesized aryl thiazolyl-thiophene dyes as sensitizers. The promising results of JSC (2.46 × 10-2 and 4.07 × 10-2 mA/cm2), the VOC (0.429 V and 0.426 V) and the FF (0.66 %) values obtained compared to other organic and natural sensitizer were due to the better interaction between the carboxyl and carbonyl groups of aryl azo molecule attached to the thiazolyl nucleus and the surface of TiO2 porous film. [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]

In this work, we have synthesized a series of novel porphyrin derivatives, 1 – 5, in high yields. The metal complexes of two of the newly synthesized porphyrin derivatives, 1a–d and 2a–d, have also been synthesized in high yields and characterized. In the synthesis of the new porphyrins and metalloporphrins, we employed our reported strategy in which we utilized N,N -dimethylformamide (DMF) as a capping agent in the reaction of pyrrole with different hetero-aryl aldehydes. The new porphyrin derivatives are equipped with different aromatic substituents and hetero-cycles at the peripheral position. The structures of the new compounds were confirmed by elemental and spectral analyses. The geometry and magnetic properties of the new metalloporphyrins 1a–d and 2a–d have also been studied. Antioxidant and cytotoxic activities of the new compounds were evaluated and structure-activity relationships were performed. Porphyrin derivatives 2a and 4 showed exceptional antioxidant activity compared to ascorbic acid as a reference. While the derivatives 2, 3, and 5 exhibited very strong cytotoxic activity against two human cell lines, HePG-2 and MCF-7. Docking for the most promising antioxidant porphyrins, 2a and 4, into the binding active site of antioxidant protein Human Peroxiredoxin (code: 1HD2) has been carried out to detect the degree of recognition antioxidant activity. Molecular docking of the most cytotoxic active porphyrins, 3 and 5, into the biding site of telomerase inhibitor enzyme has been carried out to assess the degree of recognition cytotoxic activity. Compound 5 with gigantic phenothiazine functions is one of the promising lead in the treatment of cancer as it showed highest cytotoxic activity against MCF7 cell line and proper complementarity with G-quartet 2A5R protein. Image 1 • One-pot synthesis using DMF as a solvent and a capping agent is the most effective synthetic route for porphyrins. • Copper complexes of porphyrins are the most effective antioxidants among other metalloporphyrin derivatives. • The antioxidant activity of copper porphyrins is due to the ability of the central metal to get reduced from Cu(II) to Cu(I). [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]

The synthesis, description, and demonstration of dye-sensitive solar cell sensitizers containing bifuran/biphenyl derivatives with cyanoacetic acid, barbiturate, thiobarbituric acid, and 4-carboxylcyanoacetamides have been reported. A photovoltaic performance measurement was conducted using the Ru(ii) dye N3 as a reference to examine the effects of different electron acceptor units and replacement of the π-spacer bifuran by biphenyl units on the photophysical, electrochemical, and photovoltaic properties of eight new distinct organic dyes HB-1-8. The new organic dyes HB-1-8 were prepared and compared with the N3 metal dye. Density functional theory calculations were carried out to explore the ground state geometrical structures and electronic structures of the eight dyes. Under standard global AM 1.5 solar condition, the solar cells based on HB-1-8 show the overall power conversion efficiencies of 2.93-5.51%. The presented research shows that the organic dye photovoltaic performances can vary greatly depending on the type of electron donor and acceptor used. Dye HB-3 exhibited the highest efficiency among the eight investigated dyes, reaching 5.51% with a V OC value higher than N3., Competing Interests: The authors declare no conflict of interest, financial or otherwise., (This journal is © The Royal Society of Chemistry.)

A new series of metal-free organic dyes (SM1-5) with dual anchors are synthesized for application in dye-sensitized solar cells (DSSC). Here, a simple triphenylamine (TPA) moiety serves as the electron donor, while di-cyanoacrylamide and di-thiazolidine-5-one units serve as the electron acceptors and anchoring groups. To understand the effect of dye structure on the photovoltaic characteristics of DSSCs, the photophysical and electrochemical properties, as well as molecular geometries calculated from density functional theory (DFT), are used for dyes SM1-5. The extinction coefficients of the organic dyes SM1-5 are high (5.36-9.54 10 4  M -1  cm -1 ), indicating a high aptitude for light harvesting. The photovoltaic studies indicated that using dye SM4 as a sensitizer showed a power conversion efficiency (PCE) of 6.09% (J SC  = 14.13 mA cm -2 , V OC  = 0.624 V, FF = 68.89%). Interestingly, SM4 showed the highest values of V OC among all dyes, including N-719, due to its maximum dye coverage on the TiO 2 surface, enhancing charge recombination resistance in the sensitized cell. The good agreement between the theoretically and experimentally obtained data indicates that the energy functional and basis set employed in this study can be successfully utilized to predict new photosensitizers' absorption spectra with great precision before synthesis. Also, these results show that bi-anchoring molecules have a lot of potentials to improve the overall performance of dye-sensitized solar cells., (© 2022. The Author(s).)

New phthalonitrile derivatives formed from reactions of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) were considered as the key intermediates for the synthesis of new phthalocyanines. Moreover, new phthalonitrile derivatives 2, 5, 9, 10, 15 and 16 reacted with 1,4-diazabicyclo[2.2.2]octane (DBO) or hydroquinone to afford the corresponding new phthalocyanine dyes 3, 6, 11, 12, 17 and 18. In addition, the cyclotetramerization of phthalic anhydride derivative 20 afforded new phthalocyanine dye 22. Spectral and elemental investigations revealed the structures of the newly synthesized phthalocyanines. The antioxidant and cytotoxic properties of the novel compounds were investigated, and it has been established that compounds 17 and 18 have very strong anticancer and antioxidant action against all cell lines., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)

In this study, some novel cyanine dyes, 1, 3, and 5-15, were synthesized by a one-pot step reaction of pyridinium salts 2 and/or 4 with benzenaminium salt 1. N-{[1-Chloro-3,4-dihydronaphthalen-2-yl)methylene]benzenaminium} chloride 1 was obtained by the reaction of α-tetralone with Vilsmeier-Haack reagent, followed by a mixture of an equimolar ratio of anilin/ethanol (1:1). All new cyanine dyes were evaluated in vitro for their anticancer activity against two cell lines, that is, HepG2 (human hepatocellular liver carcinoma) and MCF-7 (breast cancer). The obtained results were compared with human lung fibroblasts (WI-38) and Vero cells (derived from the kidney of an African green monkey) as normal cells. In particular, some of these compounds, 6, 9, 13, and 14, were found to be the most potent derivatives against all the cancer cell lines, without effect on the normal cells. According to the structure-activity relationship, compound 13 (IC 50  = 8.8 µg/ml) exhibited a higher activity against HepG2 cells, as it contains the azo group and two phenyl rings and due to the presence of the π-conjugated system attached to the two pyridine rings. Compound 6 (IC 50  = 8 µg/ml) exhibited a higher activity against MCF-7 cells, as it contains two chlorine atoms and the π-conjugated system of the pyridine rings., (© 2020 Deutsche Pharmazeutische Gesellschaft.)

The reaction of 2-(cyanomethyl)benzonitrile (1) with different diazonium salts gave the corresponding aryldiazenyl derivatives 2a-e which reacted with sodium hydroxide and ethyl chloroacetate and hydroxylamine hydrochloride to afford the corresponding acetamides 4a-e, pyrazoloisoquinolines 6a-e and triazoloisoquinoline derivatives 8a-e, respectively. Moreover, the reaction of 1 with arylidene malononitriles 9a-c afforded dihydronaphthalenes 11a, b and naphthalene derivative 12, respectively. The newly synthesized compounds were characterized by analytical and spectral data. The investigated compounds were screened for their antibacterial activity against Gram-positive bacteria, Gram-negative bacteria and antifungal activity. Among the synthesized compounds, (E)-2-(cyano((4-nitrophenyl)diazenyl)methyl)benzonitrile (2e) exhibited a significant activity toward both Gram-positive, Gram-negative bacteria and exhibit the most potent in vitro antifungal with MIC's (6.25 μg/mL) against Botrytis fabae., (Copyright © 2012 Elsevier Masson SAS. All rights reserved.)

The base-catalyzed reaction of benzoyl acetone 1 with phenyl isothiocyanate yields the non-isolable intermediate 2. Treatment of 2 with dilute HCl afforded the corresponding thiocarbamoyl derivative 3. Reaction of the intermediate 2 with phenacyl bromide, ethyl bromoacetate, chloroacetonitrile, chloroacetyl chloride, bromodiethyl malonate and chloroacetone afforded the corresponding thiophene derivatives 5, 8, 15 and 17. The thiocarbamoyl derivative 3 reacts with arylazophenacyl bromide and/or hydrazine hydrate to afford the corresponding thiadiazole and pyrazole derivatives 20a-c and 22, respectively. These new synthesized compounds show generally a moderate molluscicidal activity to Biomphalaria alexandrina snails.

The thiosemicarbazones (3 and 6) and N-arylidene cyanoacetohydrazide (12) were prepared and used as key intermediates for the synthesis of 4-thiazolidinones (4, 5, 7-9), thiazoles (10a,b and 11a-d) and thiazoline (13) derivatives. Treatment of 13 with a mixture of triethylorthoformate and acetic anhydride afforded thiazolo[5,4-d]pyrimidinone derivative (14). The newly synthesized compounds were characterized by IR, (1)H NMR and mass spectral studies. Representative compounds of the synthesized products were tested and evaluated as antimicrobial agents.