(2-amino-6-cyclohexylthiocarbamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone | 1078692-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-amino-6-cyclohexylthiocarbamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone
• 英文别名: 2-amino-N-cyclohexyl-3-(3,4,5-trimethoxybenzoyl)-5,7-dihydro-4H-thieno[2,3-c]pyridine-6-carbothioamide
• CAS: 1078692-20-2
• 化学式: C₂₄H₃₁N₃O₄S₂
• 分子量: 489.66
• InChiKey: GLVUUJONLZKJIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2-acetylamino-6-cyclohexylthiocarbamoyl-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56%的产率得到(2-amino-6-cyclohexylthiocarbamoyl-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

文献信息

• 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
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Olga Cruz-Lopez、Carlota Lopez Cara、Manlio Tolomeo、Stefania Grimaudo、Antonietta Di Cristina、Maria Rosa Pipitone、Jan Balzarini、Sahar Kandil、Andrea Brancale、Taradas Sarkar、Ernest Hamel

  DOI：10.1016/j.bmcl.2008.08.006

  日期：2008.9

  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.