A new series of thiophene anchored 1,3,4-thiadiazole, 1,2,4-triazole, 2-heteryl chromone, 1,5-benzothiazepine, pyrazoline, 2-styryl chromone derivatives containing fluorine are synthesized, characterized by spectral methods and screened them for various biological activities.
Novel 1‐benzyl‐3‐(4‐fluorophenyl)‐1H‐pyrazole‐4‐carbaldehydes 3a to 3e were synthesized via Vilsmeier‐Haack reaction of the appropriate 1‐benzyl‐2‐(1‐(4‐fluorophenyl)ethylidene)hydrazines, derived from 4‐fluoroacetophenone 1 with substituted 2‐benzylhydrazines 2a to 2e. The base catalyzed condensation of 1‐benzyl‐3‐(4‐fluorophenyl)‐1H‐pyrazole‐4‐carbaldehydes 3a to 3e with 1‐(4‐fluoro‐2‐hydroxyphenyl)ethanone 4 gave (E)‐3‐(1‐benzyl‐3‐(4‐fluorophenyl)‐1H‐pyrazol‐4‐yl)‐1‐(4‐fluoro‐2‐hydroxyphenyl)prop‐2‐en‐1‐ones 5a to 5e. On cyclization with dimethyl sulfoxide (DMSO)/I2, compounds 5a to 5e gave 2‐(1‐benzyl‐3‐(4‐fluorophenyl)‐1H‐pyrazol‐4‐yl)‐7‐fluoro‐4H‐chromen‐4‐ones 6a to 6e. Structures of all novel compounds were confirmed by infrared (IR), proton nuclear magnetic resonance (1H NMR), carbon nuclear magnetic resonance (13C NMR), and mass spectral data. All the synthesized compounds were screened for their antibacterial activities.
A series of novel 1,3,4‐thiadiazoles, 1,2,4‐triazoles, and 1,3,4‐oxadiazoles were synthesized by cyclization of substituted 1‐(2‐(2‐chlorophenyl)‐2‐(4‐(2,3‐dichlorophenyl)piperazin‐1‐yl)acetyl)thiosemicarbazide. The structures of all newly synthesized compounds were elucidated on the basis of spectral studies. Some of them were screened for their antibacterial activity. The compounds 6b, 6c, 8e, 9a, and 9b have shown moderate activity towards Bacillus Subtilis and Escherichia Coli.
In search of new active molecules, a small focused library of the synthesis of 3‐(trifluoromethyl)‐1‐(perfluorophenyl)‐1H‐pyrazol‐5(4H)‐one derivatives (4a‐d, 5a‐f, and 6a‐e) has been efficiently prepared via the Knoevenagel condensation approach. All the derivatives were synthesized by conventional and nonconventional methods like ultrasonication and microwave irradiation, respectively. Several derivatives exhibited excellent anti‐inflammatory activity compared to the standard drug. Furthermore, the synthesized compounds were found to have potential antioxidant activity. In addition, to rationalize the observed biological activity data, an in silico absorption, distribution, metabolism, and excretion (ADME) prediction study also been carried out. The results of the in vitro and in silico studies suggest that the 3‐(trifluoromethyl)‐1‐(perfluorophenyl)‐1H‐pyrazol‐5(4H)‐one derivatives (4a‐d, 5a‐f, and 6a‐e) may possess the ideal structural requirements for the further development of novel therapeutic agents.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.