ethyl 2-amino-3-(3,4,5-trimethoxybenzoyl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate | 1078691-82-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-amino-3-(3,4,5-trimethoxybenzoyl)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxylate
• 英文别名: 2-Amino-3-(3',4',5'-trimethoxybenzoyl)-6-ethoxycarbonyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine；ethyl 2-amino-3-(3,4,5-trimethoxybenzoyl)-5,7-dihydro-4H-thieno[2,3-c]pyridine-6-carboxylate
• CAS: 1078691-82-3
• 化学式: C₂₀H₂₄N₂O₆S
• 分子量: 420.486
• InChiKey: SSKJTKDNJZBUOL-UHFFFAOYSA-N

物化性质

• 熔点：
  65-67 °C
• 沸点：
  649.2±55.0 °C(predicted)
• 密度：
  1.300±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  3,4,5-三甲氧基苯甲酰乙腈 、 N-乙氧羰基-4-哌啶酮 在 sulfur 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以62%的产率得到ethyl 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