5-Methylbenzothiophen-3-carbaldehyd | 32969-19-0

• 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: 5-Methylbenzothiophen-3-carbaldehyd
• 英文别名: 5-methylbenzothiophene-3-carboxaldehyde；5-methyl-benzo[b]thiophene-3-carbaldehyde；5-Methylbenzo[b]thiophene-3-carbaldehyde；5-methyl-1-benzothiophene-3-carbaldehyde
• CAS: 32969-19-0
• 化学式: C₁₀H₈OS
• 分子量: 176.239
• InChiKey: CICXVKAEDHCPKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-甲基苯并噻吩 、 1,1-二氯甲醚 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到5-Methylbenzothiophen-3-carbaldehyd
  参考文献：
  名称：

  Antitumor Agents. 284. New Desmosdumotin B Analogues with Bicyclic B-Ring as Cytotoxic and Antitubulin Agents

  摘要：

  We previously reported that the biological activity of analogues of desmosdumotin B (1) was dramatically changed depending on the B-ring system. A naphthalene B-ring analogue 3 exerted potent in vitro activity against a diverse panel of human tumor cell lines with GI(50) values of 0.8-2.1 mu M. In contrast, 1 analogues with a phenyl B-ring showed unique selective activity against P-glycoprotein (P-gp) over-expressing multidrug resistant cell line. We have now prepared and evaluated, 1 analogues with bicyclic or tricyclic aromatic B-ring systems as in vitro inhibitors of human cancer cell line proliferation. Among all synthesized derivatives, 21 with a benzo[b]thiophenyl B-ring was highly active, with GI(50) values of 0.06-0.16 mu M, and this activity was not influenced by overexpression of P-gp. Furthermore, 21 inhibited tubulin assembly in vitro with an IC(50) value of 2.0 mu M and colchicine binding by 7896 as well as cellular microtubule polymerization and spindle formation.

  DOI：

  10.1021/jm1011947

文献信息

• Antitumor Agents. 284. New Desmosdumotin B Analogues with Bicyclic B-Ring as Cytotoxic and Antitubulin Agents
  作者：Kyoko Nakagawa-Goto、Pei-Chi Wu、Chin-Yu Lai、Ernest Hamel、Hao Zhu、Liying Zhang、Takashi Kozaka、Emika Ohkoshi、Masuo Goto、Kenneth F. Bastow、Kuo-Hsiung Lee

  DOI：10.1021/jm1011947

  日期：2011.3.10

  We previously reported that the biological activity of analogues of desmosdumotin B (1) was dramatically changed depending on the B-ring system. A naphthalene B-ring analogue 3 exerted potent in vitro activity against a diverse panel of human tumor cell lines with GI(50) values of 0.8-2.1 mu M. In contrast, 1 analogues with a phenyl B-ring showed unique selective activity against P-glycoprotein (P-gp) over-expressing multidrug resistant cell line. We have now prepared and evaluated, 1 analogues with bicyclic or tricyclic aromatic B-ring systems as in vitro inhibitors of human cancer cell line proliferation. Among all synthesized derivatives, 21 with a benzo[b]thiophenyl B-ring was highly active, with GI(50) values of 0.06-0.16 mu M, and this activity was not influenced by overexpression of P-gp. Furthermore, 21 inhibited tubulin assembly in vitro with an IC(50) value of 2.0 mu M and colchicine binding by 7896 as well as cellular microtubule polymerization and spindle formation.