propyl 2-amino-3-(3,4,5-trimethoxybenzoyl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate | 1078691-86-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propyl 2-amino-3-(3,4,5-trimethoxybenzoyl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate
• 英文别名: propyl 2-amino-3-(3,4,5-trimethoxybenzoyl)-5,7-dihydro-4H-thieno[2,3-c]pyridine-6-carboxylate
• CAS: 1078691-86-7
• 化学式: C₂₁H₂₆N₂O₆S
• 分子量: 434.513
• InChiKey: WTBVMXMRARAFQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  n-propyl 4-oxopiperidine-1-carboxylate 、 3,4,5-三甲氧基苯甲酰乙腈 在 sulfur 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以74%的产率得到propyl 2-amino-3-(3,4,5-trimethoxybenzoyl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate
  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.