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Heterocycles [h]fused onto 4-oxoquinoline-3-carboxylic acid, part IV. Convenient synthesis of substituted hexahydro [1,4]thiazepino[2,3-h]quinoline-9-carboxylic acid and its tetrahydroquino[7,8-b]benzothiazepine homolog.稠合于4-氧代喹啉-3-羧酸上的杂环[h]，第四部分。取代的六氢[1,4]噻氮杂卓并[2,3-h]喹啉-9-羧酸及其四氢喹啉并[7,8-b]苯并噻嗪同系物的简便合成。
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Studies on the chemistry of thienoannelated O,N- and S,N-containing heterocycles. Part 19: thieno[2,3-b][1,4]thiazines with calcium antagonistic and potassium opening activities.
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一些新型吡啶并[3',2':4,5]噻吩并[2,3 - b][1,4]噻嗪 - 8 - 羧酸的简便合成

Facile synthesis of some novel pyrido[3',2':4,5]thieno[2,3-b][1,4]thiazine-8-carboxylic acids.

作者信息

Al-Huniti Mohammed H, El-Abadelah Mustafa M, Zahra Jalal A, Sabri Salim S, Ingendoh Arnd

机构信息

Chemistry Department, Faculty of Science, The University of Jordan, Amman 11942, Jordan.

出版信息

Molecules. 2007 Mar 15;12(3):497-503. doi: 10.3390/12030497.

DOI:10.3390/12030497
PMID:17851406
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6149376/
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 alpha-mercaptoacetic, alpha-mercaptopropionic, and alpha-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.

摘要

通过使用连二亚硫酸钠对相应的2-[(羧基烷基)硫基]-3-硝基-4,7-二氢噻吩并[2,3-b]吡啶-5-羧酸7a-c进行还原内酰胺化反应，合成了模型四氢吡啶并[3',2':4,5]噻吩并[2,3-b][1,4]噻嗪9a-c。后一种衍生物是通过2-氯-7-环丙基-3-硝基-4,7-二氢噻吩并[2,3-b]吡啶-5-羧酸(6)与α-巯基乙酸、α-巯基丙酸和α-巯基琥珀酸以及三乙胺在室温下于丙酮水溶液中相互作用制得的。7a-7c和9a-9c的结构得到了微量分析和光谱(红外、质谱、核磁共振)数据的支持。化合物9a和9c对IGROV1(卵巢癌)细胞系表现出强效抑制活性。