4H-Thieno(2',3':4,5)pyrimido(2,1-b)benzothiazole-2-carboxylic acid, 3-methyl-4-oxo-, ethyl ester | 159852-69-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 4H-Thieno(2',3':4,5)pyrimido(2,1-b)benzothiazole-2-carboxylic acid, 3-methyl-4-oxo-, ethyl ester
• 英文别名: ethyl 14-methyl-16-oxo-8,12-dithia-1,10-diazatetracyclo[7.7.0.02,7.011,15]hexadeca-2,4,6,9,11(15),13-hexaene-13-carboxylate
• CAS: 159852-69-4
• 化学式: C₁₆H₁₂N₂O₃S₂
• 分子量: 344.415
• InChiKey: LUKOMMUFCIOFLK-UHFFFAOYSA-N

物化性质

• 熔点：
  156-158 °C(Solv: 1,4-dioxane (123-91-1))
• 沸点：
  571.7±60.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氯苯并噻唑 、 2-氨-4-甲基噻吩-3,5-二羧酸二乙酯 反应 2.0h， 以58%的产率得到4H-Thieno(2',3':4,5)pyrimido(2,1-b)benzothiazole-2-carboxylic acid, 3-methyl-4-oxo-, ethyl ester
  参考文献：
  名称：

  Synthesis of new thienopyrimidobenzothiazoles and thienopyrimidobenzoxazoles with analgesic and antiinflammatory properties

  摘要：

  As an extension of research on analgesic and antiinflammatory compounds, a series of substituted analogues based on the novel 4H-thieno[2',3':4,5]pyrimido[2,1-b]benzothiazole and 4H-thieno[2',3':4,5]pyrimido[2,1-b]benzoxazole ring systems was synthesized. The compounds were obtained by reaction of 2 amino-3-carbethoxy-4,5-disubstituted thiophenes with 2-chlorobenzothiazole and 2-chlorobenzoxazole, respectively. Starting from 2-carbomethoxy-3-aminothiophene, 11H-thieno[3',2':4,5]pyrimido[2,1-b]benzothiazol-11-one and 11H-thieno[3',2':4,5]pyrimido[2,1-b]benzoxazol-11-one were prepared in the same way. Synthesized compounds were evaluated for their potential analgesic activity in phenylquinone-induced writhing test in mice and fdr their potential antiinflammatory activity in carrageenan-induced rat-paw oedema test, in acetic-acid peritonitis assay and in croton oil-induced mouse-ear oedema test. 9,10,11,12-Tetrahydro-12H-benzothieno[2',3':4,5]pyrimido[2,1-b]benzoxazol-12-one 12 was the most active derivative in the series in all performed tests. It showed remarkable analgesic and antiinflammatory activities associated with an excellent gastric tolerance.

  DOI：

  10.1016/0223-5234(94)90149-x

文献信息

• The Utility of Isothiocyanato Thiophenes in the Synthesis of Thieno[2,3-<i>d</i>]pyrimidine Derivatives as Possible Radioprotective and Anticancer Agents
  作者：M. M. Ghorab、A. N. Osman、E. Noaman、H. I. Heiba、N. H. Zaher

  DOI：10.1080/10426500500544238

  日期：2006.9.1

  The synthesis of novel thioureido derivatives 3, 8, and 10; biscompounds 7, 9, and 11; and tetracyclic compounds 5, 6, and 16 utilizing 5-isothiocyanato-3-methyl-thiophene-2,4-dicarboxylic acid diethyl ester 2 are reported. The structures of these compounds were confirmed by microanalyses and IR, H-1 NMR, and mass spectroscopy. Preliminary biological studies of some of the synthesized compounds showed promising radioprotective and anticancer activities.