3-chloro-N-(4-pyridyl)benzo[b]thiophene-2-carboxamide hydrochloride | 1147274-46-1

• 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-N-(4-pyridyl)benzo[b]thiophene-2-carboxamide hydrochloride
• 英文别名: 3-chloro-N-pyridin-1-ium-4-yl-1-benzothiophene-2-carboxamide;chloride
• CAS: 1147274-46-1
• 化学式: C₁₄H₉ClN₂OS*ClH
• 分子量: 325.218
• InChiKey: IJSIGKZRQSSASF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  20
• 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：
  70.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-chloro-N-(4-pyridyl)benzo<β>thiophene-2-carboxamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以80.2%的产率得到3-chloro-N-(4-pyridyl)benzo[b]thiophene-2-carboxamide hydrochloride
  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.