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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

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Received: 8 March 2007; in revised form: 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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.



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