Acetamide, N-[(7S)-5,6,7,9-tetrahydro-10-[[2-(3-hydroxy-1-piperidinyl)ethyl]amino]-1,2,3-trimethoxy-9-oxobenzo[a]heptalen-7-yl]- | 1415569-00-4

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: Acetamide, N-[(7S)-5,6,7,9-tetrahydro-10-[[2-(3-hydroxy-1-piperidinyl)ethyl]amino]-1,2,3-trimethoxy-9-oxobenzo[a]heptalen-7-yl]-
• 英文别名: N-[(7S)-10-[2-(3-hydroxypiperidin-1-yl)ethylamino]-1,2,3-trimethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• CAS: 1415569-00-4
• 化学式: C₂₈H₃₇N₃O₆
• 分子量: 511.618
• InChiKey: YAGNRHBMSJSKII-BPARTEKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-hydroxypiperidin-1-ylacetonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 Acetamide, N-[(7S)-5,6,7,9-tetrahydro-10-[[2-(3-hydroxy-1-piperidinyl)ethyl]amino]-1,2,3-trimethoxy-9-oxobenzo[a]heptalen-7-yl]-
  参考文献：
  名称：

  Synthesis and biological evaluation of colchicine C-ring analogues tethered with aliphatic linkers suitable for prodrug derivatisation

  摘要：

  Colchicine was modified at the 10-OCH3 position of the C-ring by reaction with heterocyclic amines or commercially available amines to afford a library of target colchicinoids in high yields (62-99%). Molecular modeling revealed that the incorporation of the linker groups led to a reduction in entropy and therefore binding affinity when compared with colchicine. Some colchicinoids were shown to be equicytotoxic with colchicine when evaluated in the DLD-1 colon cancer cells and retained activity in resistant A2780AD or HeLa cells with mutant Class III beta-tubulin. Importantly, unlike colchicine, the analogues in this study are amenable for prodrug derivatisation and with potential for tumor-selective delivery. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.104

文献信息

• Synthesis and biological evaluation of colchicine C-ring analogues tethered with aliphatic linkers suitable for prodrug derivatisation
  作者：Jérémie Fournier-Dit-Chabert、Victoria Vinader、Ana Rita Santos、Mariano Redondo-Horcajo、Aurore Dreneau、Ramkrishna Basak、Laura Cosentino、Gemma Marston、Hamdy Abdel-Rahman、Paul M. Loadman、Steven D. Shnyder、José Fernando Díaz、Isabel Barasoain、Robert A. Falconer、Klaus Pors

  DOI：10.1016/j.bmcl.2012.09.104

  日期：2012.12

  Colchicine was modified at the 10-OCH3 position of the C-ring by reaction with heterocyclic amines or commercially available amines to afford a library of target colchicinoids in high yields (62-99%). Molecular modeling revealed that the incorporation of the linker groups led to a reduction in entropy and therefore binding affinity when compared with colchicine. Some colchicinoids were shown to be equicytotoxic with colchicine when evaluated in the DLD-1 colon cancer cells and retained activity in resistant A2780AD or HeLa cells with mutant Class III beta-tubulin. Importantly, unlike colchicine, the analogues in this study are amenable for prodrug derivatisation and with potential for tumor-selective delivery. (C) 2012 Elsevier Ltd. All rights reserved.