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Facile Synthesis of Some Novel Pyrido[3', 2': 4, 5]thieno[2,3-b][1,4]thiazine-8-carboxylic Acids
Chemistry Department, Faculty of Science, The University of Jordan, Amman 11942, Jordan
University of Sharjah, Sharjah, P. O. Box 27272, United Arab Emirates (UAE)
Bruker Daltonik GmbH, Fahrenheitstr. 4, D-28359 Bremen, Germany
* Author to whom correspondence should be addressed.
Received: 8 March 2007; in revised form: 14 March 2007 / Accepted: 15 March 2007 / Published: 15 March 2007
Abstract: 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.
Keywords: 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
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Al-Huniti, M.H.; El-Abadelah, M.M.; Zahra, J.A.; Sabri, S.S.; Ingendoh, A. Facile Synthesis of Some Novel Pyrido[3', 2': 4, 5]thieno[2,3-b][1,4]thiazine-8-carboxylic Acids. Molecules 2007, 12, 497-503.
Al-Huniti MH, El-Abadelah MM, Zahra JA, Sabri SS, Ingendoh A. Facile Synthesis of Some Novel Pyrido[3', 2': 4, 5]thieno[2,3-b][1,4]thiazine-8-carboxylic Acids. Molecules. 2007; 12(3):497-503.
Al-Huniti, Mohammed H.; El-Abadelah, Mustafa M.; Zahra, Jalal A.; Sabri, Salim S.; Ingendoh, Arnd. 2007. "Facile Synthesis of Some Novel Pyrido[3', 2': 4, 5]thieno[2,3-b][1,4]thiazine-8-carboxylic Acids." Molecules 12, no. 3: 497-503.