3-chloro-benzo[b]thiophene-(5-cyanopyridin-2-yl)-2-carboxamide | 1147274-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-chloro-benzo[b]thiophene-(5-cyanopyridin-2-yl)-2-carboxamide
• 英文别名: 3-chloro-N-(5-cyanopyridin-2-yl)-1-benzothiophene-2-carboxamide
• CAS: 1147274-53-0
• 化学式: C₁₅H₈ClN₃OS
• 分子量: 313.767
• InChiKey: GLFHCCJGIFKSQV-UHFFFAOYSA-N

物化性质

• 熔点：
  244-246 °C(Solvent: Methanol)
• 沸点：
  459.5±45.0 °C(predicted)
• 密度：
  1.50±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-benzo[b]thiophene-(5-cyanopyridin-2-yl)-2-carboxamide 以 甲醇 、 甲苯 为溶剂， 反应 10.0h， 以55%的产率得到6-oxo-5H-[1]benzothiolo[2,3-c][1,8]naphthyridine-2-carbonitrile
  参考文献：
  名称：

  Novel Derivatives of Pyridylbenzo[b]thiophene-2-carboxamides and Benzo[b]thieno[2,3-c]naphthyridin-2-ones: Minor Structural Variations Provoke Major Differences of Antitumor Action Mechanisms

  摘要：

  Novel cyano- and 2-imidazolinyl-substituted derivatives of pyridylbenzo[b]thiophene-2-carboxamides 4, 5, 10-13 and benzo[b]thieno[2,3-c]naphthyridin-2-ones 6, 7, 14-17 were prepared. All derivatives showed a prominent antiproliferative effect. Extensive DNA binding studies and additional biological evaluations point to various modes/targets of action. The results strongly support intercalation into DNA as a dominant binding mode of fused analogues, which was substantiated using topoisomerase I inhibition assay. Most intriguingly, only minor structural difference between "nonfused" compounds 12 and 13 has strong impact on the interactions with DNA; while 13 binds within the DNA minor groove in the form of dimer, 12 does not form significant interactions with DNA. The assumption that severe mitotic impairment (G2/M phase arrest) induced by 12 could point to tubulin, another important target, was confirmed by its obvious anti-tubulin activity observed in immunofluorescence assay, whereby treated cells showed disruption of microtubule formation comparable to the effect obtained by paclitaxel. a well-known tubulin antagonist chemotherapeutic.

  DOI：

  10.1021/jm801573v
• 作为产物：
  描述：

  2-氨基-5-氰基吡啶 、 3-氯苯并ób]噻酚-2-羰酰氯 在 三乙胺 作用下， 以 甲苯 为溶剂， 以40%的产率得到3-chloro-benzo[b]thiophene-(5-cyanopyridin-2-yl)-2-carboxamide
  参考文献：
  名称：

  Novel Derivatives of Pyridylbenzo[b]thiophene-2-carboxamides and Benzo[b]thieno[2,3-c]naphthyridin-2-ones: Minor Structural Variations Provoke Major Differences of Antitumor Action Mechanisms

  摘要：

  Novel cyano- and 2-imidazolinyl-substituted derivatives of pyridylbenzo[b]thiophene-2-carboxamides 4, 5, 10-13 and benzo[b]thieno[2,3-c]naphthyridin-2-ones 6, 7, 14-17 were prepared. All derivatives showed a prominent antiproliferative effect. Extensive DNA binding studies and additional biological evaluations point to various modes/targets of action. The results strongly support intercalation into DNA as a dominant binding mode of fused analogues, which was substantiated using topoisomerase I inhibition assay. Most intriguingly, only minor structural difference between "nonfused" compounds 12 and 13 has strong impact on the interactions with DNA; while 13 binds within the DNA minor groove in the form of dimer, 12 does not form significant interactions with DNA. The assumption that severe mitotic impairment (G2/M phase arrest) induced by 12 could point to tubulin, another important target, was confirmed by its obvious anti-tubulin activity observed in immunofluorescence assay, whereby treated cells showed disruption of microtubule formation comparable to the effect obtained by paclitaxel. a well-known tubulin antagonist chemotherapeutic.

  DOI：

  10.1021/jm801573v

文献信息

• Novel Derivatives of Pyridylbenzo[<i>b</i>]thiophene-2-carboxamides and Benzo[<i>b</i>]thieno[2,3-<i>c</i>]naphthyridin-2-ones: Minor Structural Variations Provoke Major Differences of Antitumor Action Mechanisms
  作者：Katja Ester、Marijana Hranjec、Ivo Piantanida、Irena Ćaleta、Ivana Jarak、Krešimir Pavelić、Marijeta Kralj、Grace Karminski-Zamola

  DOI：10.1021/jm801573v

  日期：2009.4.23

  Novel cyano- and 2-imidazolinyl-substituted derivatives of pyridylbenzo[b]thiophene-2-carboxamides 4, 5, 10-13 and benzo[b]thieno[2,3-c]naphthyridin-2-ones 6, 7, 14-17 were prepared. All derivatives showed a prominent antiproliferative effect. Extensive DNA binding studies and additional biological evaluations point to various modes/targets of action. The results strongly support intercalation into DNA as a dominant binding mode of fused analogues, which was substantiated using topoisomerase I inhibition assay. Most intriguingly, only minor structural difference between "nonfused" compounds 12 and 13 has strong impact on the interactions with DNA; while 13 binds within the DNA minor groove in the form of dimer, 12 does not form significant interactions with DNA. The assumption that severe mitotic impairment (G2/M phase arrest) induced by 12 could point to tubulin, another important target, was confirmed by its obvious anti-tubulin activity observed in immunofluorescence assay, whereby treated cells showed disruption of microtubule formation comparable to the effect obtained by paclitaxel. a well-known tubulin antagonist chemotherapeutic.