Synthesis and Antitumor Activity of 5-Phenyl-1,3-thiazole-4-sulfonamide Derivatives

Abstract

A method for the synthesis of 5-phenyl-1,3-thiazole-4-sulfonyl chloride was developed based on the cyclization of ethyl 2-{[1-(benzylsulfanyl)-2-oxo-2-phenylethyl]amino}-2-oxoacetate obtained from available reagents under the action of the Lawesson’s reagent and oxidative chlorination of the intermediate benzyl 5-phenyl-1,3thiazol-4-ylsulfide. The resulting sulfonyl chloride was converted into a series of 5-phenyl-1,3-thiazole-4-sulfonamide derivatives for which in vitro antitumor activity screening studies were performed on 60 cancer cell lines.

Tailoring of novel morpholine-sulphonamide linked thiazole moieties as dual targeting DHFR/DNA gyrase inhibitors: synthesis, antimicrobial and antibiofilm activities, and DFT with molecular modelling studies

“…The thiazole nucleus is present in many FDAapproved drugs, such as penicillin, ceftazidime, cefepime, aztreonam, and sulfathiazole (as antibiotics), abafungin (as an antifungal), ritonavir (as an anti-HIV), bleomycin (a cancer medication), pramipexole (Parkinson's disease treatment), dasatinib (chronic myeloid leukaemia treatment), meloxicam (a nonsteroidal antiinflammatory medication), nizatidine (a peptic ulcer treatment), thiamine (vitamin B 1 , as an essential micronutrient), etc. [19][20][21][22][23][24] Also importantly, it has been proven in the literature that thiazole-based sulfonamides are potent bioactive small molecules endowed with distinct inhibitory activities against several target enzymes such as carbonic anhydrase (as antiglaucoma, anticancer, etc. ), 20,25,26 SMYD3 (as anticancer), 27 aldose reductase (as antidiabetic cataract), 23 and acetylcholinesterase with butyrylcholinesterase (as anti-Alzheimer's).…”