Synthesis and biological evaluation of 2-phenylthiazole-4-carboxamide derivatives as anticancer agents

• Published in: European journal of medicinal chemistry Vol. 45; no. 11; pp. 5384 - 5389
• Main Authors: Aliabadi, Alireza, Shamsa, Fazel, Ostad, Seyed Nasser, Emami, Saeed, Shafiee, Abbas, Davoodi, Jamshid, Foroumadi, Alireza
• Format: Journal Article
• Language: English
• Published: ISSY-LES-MOULINEAUX Elsevier Masson SAS 01.11.2010; Elsevier
• Subjects: 2-Phenylthiazole-4-carboxamide; Amides - chemistry; Antineoplastic agents; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Biological and medical sciences; Cell Line, Tumor; Chemistry, Medicinal; Cytotoxicity; General aspects; Humans; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Mass Spectrometry; Medical sciences; MTT assay; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Science & Technology; Spectrophotometry, Infrared; Structure-Activity Relationship; Synthesis; Thiazole; Thiazolidines - chemical synthesis; Thiazolidines - chemistry; Thiazolidines - pharmacology; 2-Phenylthiazole-4-carboxamide; Cytotoxicity; Synthesis; Thiazole; MTT assay; SERIES; APOPTOSIS INDUCERS; DISCOVERY; Antineoplastic agent; Human; Benzene derivatives; In vitro; Cell line; Structure activity relation; Piperidine derivatives; Carboxamide; Colon; Mammary gland; Chemical synthesis; Tumor cell; Halogen Organic compounds
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2010.08.063

A series of substituted 2-phenylthiazole-4-carboxamide derivatives were synthesized as potential cytotoxic agents and evaluated against three human cancer cell lines including T47D (Breast cancer), Caco-2 (Colorectal cancer) and HT-29 (Colon cancer). The SAR of the arylacetamido pendent connected to the para-position of 2-phenylthiazole were explored. It was found that substitution at the 4-position by a methoxy group led to improvement of activity against Caco-2 cells while 2-methoxy substituent could maintain the high activity against HT-29 and T47D cell lines. Also, 3-fluoro analog showed good cytotoxic activity profile against all cell lines with IC 50 values less than 10 μg/mL. A series of substituted 2-phenylthiazole-4-carboxamide analogs were synthesized and evaluated against three human cancer cell lines. [Display omitted]