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Molecules 2007, 12(3), 497-503; doi:10.3390/12030497
Article

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

1
,
1
,
1,* , 2
 and
3
1 Chemistry Department, Faculty of Science, The University of Jordan, Amman 11942, Jordan 2 University of Sharjah, Sharjah, P. O. Box 27272, United Arab Emirates (UAE) 3 Bruker Daltonik GmbH, Fahrenheitstr. 4, D-28359 Bremen, Germany
* Author to whom correspondence should be addressed.
Received: 8 March 2007 / Revised: 14 March 2007 / Accepted: 15 March 2007 / Published: 15 March 2007
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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 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.

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