6-[(Z)-2-(3-amino-4-methoxyphenyl)-ethenyl]-4-methoxybenzo[b]thiophene | 1067716-72-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 6-[(Z)-2-(3-amino-4-methoxyphenyl)-ethenyl]-4-methoxybenzo[b]thiophene
• 英文别名: 2-methoxy-5-[(Z)-2-(4-methoxy-1-benzothiophen-6-yl)ethenyl]aniline
• CAS: 1067716-72-6
• 化学式: C₁₈H₁₇NO₂S
• 分子量: 311.404
• InChiKey: SWHQLZRVYDRWHC-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-[(Z)-2-(3-amino-4-methoxyphenyl)-ethenyl]-4-methoxybenzo[b]thiophene 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.17h， 生成 6-[(Z)-2-(3-amino-4-methoxyphenyl)-ethenyl]-4-methoxybenzo[b]thiophene hydrochloride
  参考文献：
  名称：

  Novel A-Ring and B-Ring Modified Combretastatin A-4 (CA-4) Analogues Endowed with Interesting Cytotoxic Activity

  摘要：

  A novel class of combretastatins, modified at A-ring or both A- and B-rings, mainly by replacement with benzofuran or benzo[b]thiophene, were synthesized. The new heterocombretastatins showed good cytotoxic activity on BMEC and H-460 cell lines. The aminocombretastatin 9f potently inhibits cell growth of BMEC and combretastatin-resistant HT-29 cell lines, with potential interest to treat colon carcinoma. Heterocombretastatins 9a,b inhibit tubulin polymerization similarly to CA-4 by having a binding to colchicine site five times stronger.

  DOI：

  10.1021/jm8005004
• 作为产物：
  描述：

  6-[(Z)-2-(4-methoxy-3-nitrophenyl)-ethenyl]-4-methoxybenzo[b]thiophene 在 溶剂黄146 、 锌 作用下， 反应 2.0h， 生成 6-[(Z)-2-(3-amino-4-methoxyphenyl)-ethenyl]-4-methoxybenzo[b]thiophene
  参考文献：
  名称：

  Novel A-Ring and B-Ring Modified Combretastatin A-4 (CA-4) Analogues Endowed with Interesting Cytotoxic Activity

  摘要：

  A novel class of combretastatins, modified at A-ring or both A- and B-rings, mainly by replacement with benzofuran or benzo[b]thiophene, were synthesized. The new heterocombretastatins showed good cytotoxic activity on BMEC and H-460 cell lines. The aminocombretastatin 9f potently inhibits cell growth of BMEC and combretastatin-resistant HT-29 cell lines, with potential interest to treat colon carcinoma. Heterocombretastatins 9a,b inhibit tubulin polymerization similarly to CA-4 by having a binding to colchicine site five times stronger.

  DOI：

  10.1021/jm8005004

文献信息

• Novel A-Ring and B-Ring Modified Combretastatin A-4 (CA-4) Analogues Endowed with Interesting Cytotoxic Activity
  作者：Daniele Simoni、Romeo Romagnoli、Riccardo Baruchello、Riccardo Rondanin、Giuseppina Grisolia、Marco Eleopra、Michele Rizzi、Manlio Tolomeo、Giuseppe Giannini、Domenico Alloatti、Massimo Castorina、Marcella Marcellini、Claudio Pisano

  DOI：10.1021/jm8005004

  日期：2008.10.9

  A novel class of combretastatins, modified at A-ring or both A- and B-rings, mainly by replacement with benzofuran or benzo[b]thiophene, were synthesized. The new heterocombretastatins showed good cytotoxic activity on BMEC and H-460 cell lines. The aminocombretastatin 9f potently inhibits cell growth of BMEC and combretastatin-resistant HT-29 cell lines, with potential interest to treat colon carcinoma. Heterocombretastatins 9a,b inhibit tubulin polymerization similarly to CA-4 by having a binding to colchicine site five times stronger.