Synthesis Of New Thiazole Derivatives Research Articles

The immobilization of L-Valine on superparamagnetic Fe3O4 nanoparticles as a novel, recoverable and green nanocatalyst for the synthesis of new thiazole derivatives

The novel immobilization of L-Valine on superparamagnetic Fe3O4 nanoparticles was prepared using a simple protocol for the first time. This compound acts as a highly efficient and recyclable heterogeneous nanocatalyst for the synthesis of thiazole derivatives via a one-pot and multi-component condensation reaction of arylglyoxals monohydrate, cyclic 1,3-dicarbonyls, and thiobenzamides in a water solvent. The structure of the nanocatalyst was characterized and confirmed using various techniques, such as Fourier transform infrared spectroscopy (FT-IR), Energy Dispersive X-ray (XRD), scanning electron microscopy (SEM), thermogravimetric analysis (TG/DTA), and vibrating sample magnetometry (VSM). This heterogeneous nanocatalyst can be easily recovered from the reaction mixture by an external magnetic field and reused for subsequent reactions at least five times without losing significant catalytic activity.

TFE assisted mechanochemical synthesis of new pyrazolones from Meldrum acid carbothioamides-Experimental and theoretical studies

Facile synthesis of Meldrum acid carbothioamides 3 from condensation of Meldrum acid and aryl isothiocyanates under ultrasonication is reported. The structure of carbothioamides was investigated in solid and solution state from X-ray diffraction and spectroscopic studies, respectively. Studies on photo-tautomerism emanating from proton switching between O and S under UV irradiation have been reported. S-methyl derivatives 4 of carbothioamides 3 were also prepared and solid state structure of the representative compound was described. Novel synthetic mechanochemical route to synthesis of functionalized pyrazolones 5 from reaction of carbothioamides 3 or their S-methyl derivatives and hydrazine hydrate in presence of 2,2,2-trifluoroethanol has been developed. The structure and proton tautomerism of pyrazolones has been assigned on spectroscopic grounds and authenticated by single crystal X-ray diffraction (SCXRD) studies. The tautomeric equilibrium between different forms of pyrazolone 5a has been studied by ab initio calculations. Experimental studies are in congruous with theoretical results. Further, synthesis of new thiazole derivatives 6 and thiazolidin-5-one derivatives 7 linked with Meldrum's acid (MA) moiety was achieved from reaction of 3 with 3-chloro-2,4-pentanedione and chloroacetyl chloride, respectively. Spectroscopic studies confirmed the structure of new developed products.

Synthesis of new thiazole derivatives and evaluation of their antimicrobial and cytotoxic activities

Novel 2-heteroaryl-N-[4-(substituted aryl)thiazol-2-yl]propanamide derivatives (7a–7o) were synthesized and investigated for their antimicrobial activity. Among the tested compounds, 2-[(1H-Benzimidazol-2-yl)thio]-N-[4-(naphthalen-2-yl)thiazol-2-yl]propanamide (7e) and N-[4-(4-Chlorophenyl)thiazol-2-yl]-2-[(1-methyl-1H-tetrazol-5-yl)thio]propanamide (7f) showed the highest antibacterial activity, whereas 2-[Benzothiazol-2-ylthio]-N-[4-(4-chlorophenyl)thiazol-2-yl]propanamide (7i) and 2-[(1H-Benzimidazol-2-yl)thio]-N-[4-(4-chlorophenyl)thiazol-2-yl]propanamide (7j) displayed anticandidal effect against C. parapsilosis and C. glabrata. The cytotoxic activity of the compounds (7a–7o) was also tested against HL-60 human leukemia cells, THP-1 human monocytic leukemia cells, and NIH/3T3 mouse embryonic fibroblast cells. Compound N-[4-(4-Chlorophenyl)thiazol-2-yl]-2-[(1-methyl-1H-imidazol-2-yl)thio]propanamide (7 g) and compound 7j exhibited high cytotoxicity against HL-60; and compounds 2-[(1-Methyl-1H-imidazol-2-yl)thio]-N-[4-(naphthalen-2-yl)thiazol-2-yl]propanamide (7b), 7 g and N-[4-(4-Methoxyphenyl)thiazol-2-yl]-2-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]propanamide (7 m) also had cytotoxic activity against THP-1 compared with standard drug with selective profile. Additionally, in silico physicochemical properties of the compounds were described.

Stereoselective synthesis, X-ray analysis, computational studies and biological evaluation of new thiazole derivatives as potential anticancer agents

BackgroundThe synthesis of new thiazole derivatives is very important because of their diverse biological activities. Also , many drugs containing thiazole ring in their skeletons are available in the market such as Abafungin, Acotiamide, Alagebrium, Amiphenazole, Brecanavir, Carumonam, Cefepime, and Cefmatilen.ResultsEthyl cyanoacetate reacted with phenylisothiocyanate, chloroacetone, in two different basic mediums to afford the thiazole derivative 6, which reacted with dimethylformamide- dimethyl acetal in the presence of DMF to afford the unexpected thiazole derivative 11. The structures of the thiazoles 6 and 11 were optimized using B3LYP/6-31G(d,p) method. The experimentally and theoretically geometric parameters agreed very well. Also, the natural charges at the different atomic sites were predicted. HOMO and LUMO demands were discussed. The anticancer activity of the prepared compounds was evaluated and showed moderate activity.ConclusionsSynthesis of novel thiazole derivatives was done. The structure was established using X-ray and spectral analysis. Optimized molecular structures at the B3LYP/6-31G(d,p) level were investigated. Thiazole derivative 11 has more electropositive S-atom than thiazole 6. The HOMO–LUMO energy gap is lower in the former compared to the latter. The synthesized compounds showed moderate anticancer activity.

Novel Thiazole Derivatives of Medicinal Potential: Synthesis and Modeling

This paper reports on the synthesis of new thiazole derivatives that could be profitably exploited in medical treatment of tumors. Molecular electronic structures have been modeled within density function theory (DFT) framework. Reactivity indices obtained from the frontier orbital energies as well as electrostatic potential energy maps are discussed and correlated with the molecular structure. X-ray crystallographic data of one of the new compounds is measured and used to support and verify the theoretical results.

Synthesis, in vitro α-glucosidase inhibitory activity and molecular docking studies of new thiazole derivatives

Current study based on the synthesis of new thiazole derivatives via “one pot” multicomponent reaction, evaluation of their in vitro α-glucosidase inhibitory activities, and in silico studies. All synthetic compounds were fully characterized by 1H NMR, 13C NMR and EIMS. CHN analysis was also performed. These newly synthesized compounds showed activities in the range of IC50=9.06±0.10–82.50±1.70μM as compared to standard acarbose (IC50=38.25±0.12μM). It is worth mentioning that most of the compounds such as 1 (IC50=23.60±0.39μM), 2 (IC50=22.70±0.60μM), 3 (IC50=22.40±0.32μM), 4 (IC50=26.5±0.40μM), 6 (IC50=34.60±0.60μM), 7 (IC50=26.20±0.43μM), 8 (IC50=14.06±0.18μM), 9 (IC50=17.60±0.28μM), 10 (IC50=27.16±0.41μM), 11 (IC50=19.16±0.19μM), 12 (IC50=9.06±0.10μM), 13 (IC50=12.80±0.21μM), 14 (IC50=11.94±0.18μM), 15 (IC50=16.90±0.20μM), 16 (IC50=12.60±0.14μM), 17 (IC50=16.30±0.29μM), and 18 (IC50=32.60±0.61μM) exhibited potent inhibitory potential. Molecular docking study was performed in order to understand the molecular interactions between the molecule and enzyme. Newly identified α-glucosidase inhibitors except few were found to be completely non-toxic.

Synthesis of New Thiazole Derivatives as Antitumor Agents

Synthesis of New Thiazole Derivatives as Antitumor Agents

Thiazole-Based Thiazolidinones as Potent Antimicrobial Agents. Design, Synthesis and Biological Evaluation

As a part of our ongoing project on the design and synthesis of new thiazole derivatives with antimicrobial activity, fourteen new ethyl 2-(2-((E)-((Z)-5-(4-benzyliden)- 4-oxothiazolidin-2-yliden)amino-4-yl)acetates, carrying halogens, methoxy and other groups were synthesized. Compounds were tested against eight Gram positive and negative bacteria as well as eight yeasts and mold by microdilution assay. All compounds showed good activity against all bacteria tested with MIC ranging between 2.3-39.8 µmol/ml x 10(-2) and MBC of 9.2-79.6 µmol/ml x 10(-2). As reference drugs Ampicillin (MIC 24.8-74.4 and MBC 37.2-124.0 µmol/ml x 10(-2)) and Streptomycin (MIC 4,3-17.2 and MBC 8.6-51.6 µmol/ml x 10(-2)) were used. The best activity was observed for 4-bromo derivative. All tested compounds showed excellent antifungal activity against all fungi tested with MIC in the range between 0.3-38.6 µmol/ml x 10(-2) and MFC range of 0.6-77.2 µmol/ml x 10(-2), better than that of reference drugs, Ketoconazole (MIC 38.0-475.0 and MFC 95.0-570 µmol/ml x 10(-2)) and Bifonazole (MIC 48.0-64.0 and MFC 64.0-80.0 µmol/ml x 10(-2)). The best activity was observed for 3-nitro derivative. It was found that among the 5-arylidene derivatives the inhibitory effect appears to be dependent on the substitution at the benzene ring. Fourteen new ethyl 2-(2-((E)-((Z)-5-(4-benzyliden)-4-oxothiazolidin-2-yliden)amino-4-yl)acetates were synthesized and evaluated for antibacterial and antifungal activity.

A Convenient and Facile Synthesis of New Thiazole Derivatives

4-Chloro-2,3-dihydrothiazole-5-carboxaldehyde reacted with some nucleophilic reagents such as hydrazine hydrate, phenyl hydrazine, urea, thiourea, semicarbazide, cyanoacetamide, cyanothio-acetamide, cyanoacetohydrazide, 2-phenylenediamine, 2-aminophenol, 5-amino[1,2,4]triazole and 3-aminopyrazole in ethanol solution at reflux in the presence of catalytic amount of triethyl-amine afforded new polysubstituted thiazolo[4,5-c]pyrazole, thiazolo[4,5-d]-pyrimidine, thiazolo[4,5-b]-pyridine, thiazolo[4,5-b][1,5]benzodiazepine, thiazolo[4,5-b] [1,5]benzoxazepine, thiazolo[4′, 5′:6,5]-pyrimido[1,2-b][1,2,4]triazole and thiazolo[4′, 5′:6,5]pyrimido[1,2-b]pyrazole derivatives in good yields. The structure of the new compounds were confirmed based on IR, 1 H-,13C-NMR, mass spectral, and elemental analysis.