Synthesis and anticancer activity of some thiophene, thienyl‐thiazole, and thienyl‐benzofuran analogues

Abstract

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.

Synthesis of Some Novel Thiophene Analogues as Potential Anticancer Agents

“…[3] Derivatives of thiophene are renowned for their extensive biological profiles, encompassing antimicrobial, [4] antiinflammatory, [5] and anti-thrombolytic properties. [6] The thiophene core, in particular, has garnered significant interest due to its observed biologically active properties. Several potential anticancer agents have been identified with the thiophene nucleus.…”

Synthesis of novel thiazol-2(3H)-imine derivatives as ergosterol biosynthesis inhibitors, and elucidation of their structures using a 2D NMR technique

“…There are also literature data showing the biological activities of imidazole and thiazole rings. 12–21…”

“…There are also literature data showing the biological activities of imidazole and thiazole rings. [12][13][14][15][16][17][18][19][20][21] There are two different reaction mechanisms for the 2,3dihydrothiazole ring system closed using N-substituted thiosemicarbazide and 2-bromoacetophenone. These predictive mechanisms are presented in Fig.…”