Synthesis and in‐vitro Cytotoxicity of Poly‐functionalized 4‐(2‐Arylthiazol‐4‐yl)‐4H‐chromenes

Abstract

A new series of 4-aryl-4H-chromenes bearing a 2-arylthiazol-4-yl moiety at the 4-position were prepared as potential cytotoxic agents. The in-vitro cytotoxic activity of the synthesized 4-aryl-4H-chromenes was investigated in comparison with etoposide, a well-known anticancer drug, using MTT colorimetric assay. Among them, the 2-(2-chlorophenyl)thiazol-4-yl analog 4b showed the most potent activity against nasopharyngeal epidermoid carcinoma KB, medulloblastoma DAOY, and astrocytoma 1321N1, and compound 4d bearing a 2-(4-chlorophenyl)thiazol-4-yl moiety at the 4-position of the chromene ring exhibited the best inhibitory activity against breast cancer cells MCF-7, lung cancer cells A549, and colon adenocarcinoma cells SW480 with IC(50 )values less than 5 microM. The ability of compound 4b to induce apoptosis was confirmed in a nuclear morphological assay by DAPI staining in the KB and MCF-7 cells.

Crystal structure of 3-amino-8-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2

“…In recent years, they have attracted considerable attention due to their antimicrobial [2,3], antileishmanial [4][5][6][7][8][9], anticancer [10][11][12][13][14][15], antiproliferative [22], antioxidant [16][17][18], hypertensive [14], antitumor [19][20][21] effects and activities, as well as proving potentially useful in the treatment of Alzheimer's disease [23] and schizophrenia disorder [24].…”

Crystal structure of 3-amino-9-methoxy-1-phenyl-1H-benzo[f]chromene-2-carbonitrile, C21H16N2O2

“…Chromene and benzochromene derivatives have attracted considerable interest owing to their biological and pharmaceutical activities such as antibacterial [1][2][3], antifungal [4][5][6], vascular-disrupting [7], antioxidant [8,9], anticancer [10][11][12][13], estrogenic anticoagulant and antispasmolytic [14], antileishmanial [15], antiproliferative and apoptosis inducing [16][17][18][19].…”

Synthesis, Cytotoxicity Assessment, and Molecular Docking of 4-Substituted-2-p-tolylthiazole Derivatives as Probable c-Src and erb Tyrosine Kinase Inhibitors

“…Diethyl ether was evaporated under reduced pressure and the product was crystallized from ethanol. 10 …”