11H-thieno<3',2':4,5>pyrimido<2,1-b>benzothiazol-11-one | 159852-73-0

• 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: 11H-thieno<3',2':4,5>pyrimido<2,1-b>benzothiazol-11-one
• 英文别名: 11H-Thieno(3'2':4,5)pyrimido(2,1-b)benzothiazol-11-one；8,14-dithia-1,10-diazatetracyclo[7.7.0.02,7.011,15]hexadeca-2,4,6,9,11(15),12-hexaen-16-one
• CAS: 159852-73-0
• 化学式: C₁₂H₆N₂OS₂
• 分子量: 258.324
• InChiKey: IQOVESQGPDBVAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  481.9±37.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯苯并噻唑 、 3-氨基-2-噻吩甲酸甲酯 反应 2.0h， 以73%的产率得到11H-thieno<3',2':4,5>pyrimido<2,1-b>benzothiazol-11-one
  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

• [EN] MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES<br/>[FR] MATÉRIAUX POUR DISPOSITIFS ÉLECTROLUMINESCENTS ORGANIQUES<br/>[DE] MATERIALIEN FÜR ORGANISCHE ELEKTROLUMINESZENZVORRICHTUNGEN
  申请人：[de]MERCK PATENT GMBH

  公开号：WO2022122682A2

  公开（公告）日：2022-06-16

  Die vorliegende Erfindung betrifft Verbindungen, die sich für die Verwendung in elektronischen Vorrichtungen eignen, sowie elektronische Vorrichtungen, insbesondere organischen Elektrolumineszenzvorrichtungen, enthaltend diese Verbindungen.
• Synthesis of new thienopyrimidobenzothiazoles and thienopyrimidobenzoxazoles with analgesic and antiinflammatory properties
  作者：F Russo、G Romeo、NA Santagati、A Caruso、V Cutuli、D Amore

  DOI：10.1016/0223-5234(94)90149-x

  日期：1994.1

  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.