Facile Synthesis of Some Novel Pyrido[3', 2': 4, 5]thieno[2,3-b][1,4]thiazine-8-carboxylic Acids

Molecules

关键词: 2-Chloro-7-cyclopropyl-3-nitro-4-oxothieno[2;    3-b]pyridine-5-carboxylic acid;    α-mercaptoalkanoic acids;    SN-Ar reaction;    reductive lactamization;    tetrahydropyrido[3';    2':4;    5]thieno[2;    3-b][1;    4] thiazines;    antitumor activity;   

DOI  :  10.3390/12030497

来源: DOAJ

【 摘 要 】

Model tetrahydropyrido[3',2':4,5]thieno[2,3-b][1,4]thiazines 9a-c were synthesized via reductive lactamization, using sodium dithionite, of the respective 2-[(carboxyalkyl)thio]-3-nitro-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acids 7a-c. The latter derivatives were made via interaction of 2-chloro-7-cyclopropyl-3-nitro-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid (6) with each of α–mercaptoacetic, α-mercaptopropionic, and α-mercaptosuccinic acids and triethylamine in aqueous acetone at room temperature. The structures of 7a-7c and 9a-9c are supported by microanalytical and spectral (IR, MS, NMR) data. Compounds 9a and 9c showed potent inhibitory activity against the IGROV1 (Ovarian Cancer) cell line.

【 授权许可】

Unknown