(2-acetylamino-6-p-fluorobenzylcarbamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone | 1078692-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-acetylamino-6-p-fluorobenzylcarbamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone
• CAS: 1078692-39-3
• 化学式: C₂₇H₂₈FN₃O₆S
• 分子量: 541.6
• InChiKey: GXRZTVKWLMEKLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  106.2
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2-acetylamino-6-p-fluorobenzylcarbamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以61%的产率得到(2-amino-6-p-fluorobenzylcarbamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-amino-3-(3′,4′,5′-trimethoxybenzoyl)-6-substituted-4,5,6,7-tetrahydrothieno[2,3-c]pyridine derivatives as antimitotic agents and inhibitors of tubulin polymerization

  摘要：

  Microtubules are among the most successful targets of compounds potentially useful for cancer therapy. A new series of inhibitors of tubulin polymerization based on the 2-amino-3-(3,4,5-trimethoxybenzoyl)-4,5,6,7-tetrahydrothieno[b]pyridine molecular skeleton was synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. The most promising compound in this series was 2-amino-3-(3,4,5-trimethoxybenzoyl)-6-methoxycarbonyl-4,5,6,7-tetrahydrothieno[b]pyridine, which inhibits cancer cell growth with IC50-values ranging from 25 to 90 nM against a panel of four cancer cell lines, and interacts strongly with tubulin by binding to the colchicine site. In this series of N-6-carbamate derivatives, any further increase in the length and in the size of the alkyl chain resulted in reduced activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.006
• 作为产物：
  描述：

  (2-acetylamino-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone 、 4-氟代苯异氰酸盐 以 二氯甲烷 为溶剂， 反应 2.0h， 以64%的产率得到(2-acetylamino-6-p-fluorobenzylcarbamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-amino-3-(3′,4′,5′-trimethoxybenzoyl)-6-substituted-4,5,6,7-tetrahydrothieno[2,3-c]pyridine derivatives as antimitotic agents and inhibitors of tubulin polymerization

  摘要：

  Microtubules are among the most successful targets of compounds potentially useful for cancer therapy. A new series of inhibitors of tubulin polymerization based on the 2-amino-3-(3,4,5-trimethoxybenzoyl)-4,5,6,7-tetrahydrothieno[b]pyridine molecular skeleton was synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. The most promising compound in this series was 2-amino-3-(3,4,5-trimethoxybenzoyl)-6-methoxycarbonyl-4,5,6,7-tetrahydrothieno[b]pyridine, which inhibits cancer cell growth with IC50-values ranging from 25 to 90 nM against a panel of four cancer cell lines, and interacts strongly with tubulin by binding to the colchicine site. In this series of N-6-carbamate derivatives, any further increase in the length and in the size of the alkyl chain resulted in reduced activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.006