N-((1S)-2''-(hydroxymethyl)-1',2',3'-trimethoxy-6,7-dihydro-1H-benzo[5',6':5,4]cyclohepta[3,2-f]benzofuran-1-yl)acetamide

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 别秋水仙碱生物碱
• 英文名称: N-((1S)-2''-(hydroxymethyl)-1',2',3'-trimethoxy-6,7-dihydro-1H-benzo[5',6':5,4]cyclohepta[3,2-f]benzofuran-1-yl)acetamide
• 英文别名: N-{(7S)-10-(hydroxymethyl)-1,2,3-trimethoxy-6,7-dihydro-5H-benzo[6',7']cyclohepta[1',2':4,5]benzo[1,2-b]furan-7-yl}acetamide；N-{(7s)-10-(hydroxymethyl)-1,2,3-trimethoxy-6,7-dihydro-5h-benzo[6',7']cyclohepta[1',2':4,5]-benzo[1,2-b]furan-7-yl}acetamide；N-[(10S)-15-(hydroxymethyl)-3,4,5-trimethoxy-14-oxatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2,4,6,12,15,17-heptaen-10-yl]acetamide
• 化学式: C₂₃H₂₅NO₆
• 分子量: 411.455
• InChiKey: JNONKELWRAOUTI-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  90.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  环戊硫醇 、 N-((1S)-2''-(hydroxymethyl)-1',2',3'-trimethoxy-6,7-dihydro-1H-benzo[5',6':5,4]cyclohepta[3,2-f]benzofuran-1-yl)acetamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以83%的产率得到N-{(7S)-1,2,3-trimethoxy-10-[(cyclopentylsulfanyl)methyl]-6,7-dihydro-5H-benzo[6',7']cyclohepta[1',2':4,5]benzo[1,2-b]furan-7-yl}acetamide
  参考文献：
  名称：

  Synthesis of new sulfur-containing derivatives of furanoallocolchicinoids

  摘要：

  Reaction of hydroxyl-containing heterocyclic colchicinoids with S-nucleophiles led to the formation of furanoallocolchicinoid sulfides in a high yield.

  DOI：

  10.1134/s1070428016080078
• 作为产物：
  描述：

  秋水仙碱 在 盐酸 、 copper(l) iodide 、 碘 、 potassium acetate 、 palladium diacetate 、 溶剂黄146 、 三苯基膦 、 sodium iodide 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 19.0h， 生成 N-((1S)-2''-(hydroxymethyl)-1',2',3'-trimethoxy-6,7-dihydro-1H-benzo[5',6':5,4]cyclohepta[3,2-f]benzofuran-1-yl)acetamide
  参考文献：
  名称：

  Synthesis of new sulfur-containing derivatives of furanoallocolchicinoids

  摘要：

  Reaction of hydroxyl-containing heterocyclic colchicinoids with S-nucleophiles led to the formation of furanoallocolchicinoid sulfides in a high yield.

  DOI：

  10.1134/s1070428016080078

文献信息

• Synthesis and Biological Evaluation of Furanoallocolchicinoids
  作者：Yuliya V. Voitovich、Ekaterina S. Shegravina、Nikolay S. Sitnikov、Vladimir I. Faerman、Valery V. Fokin、Hans-Gunther Schmalz、Sebastien Combes、Diane Allegro、Pascal Barbier、Irina P. Beletskaya、Elena V. Svirshchevskaya、Alexey Yu. Fedorov

  DOI：10.1021/jm501678w

  日期：2015.1.22

  A series of conformationally flexible furan-derived allocolchicinoids was prepared from commercially available colchicine in good to excellent yields using a three-step reaction sequence. Cytotoxicity studies indicated the potent activity of two compounds against human epithelial and lymphoid cell lines (AsPC-1, HEK293, and Jurkat) as well as against Wnt-1 related murine epithelial cell line W1308. The results of in vitro experiments demonstrated that the major effect of these compounds was the induction of cell cycle arrest in the G2/M phase as a direct consequence of effective tubulin binding. In vivo testing of the most potent furanoallocolchicinoid 10c using C57BL/6 mice inoculated with Wnt-1 tumor cells indicated significant inhibition of the tumor growth.
• Synthesis of new sulfur-containing derivatives of furanoallocolchicinoids
  作者：Yu. A. Gracheva、H.-G. Schmalz、E. V. Svirshchevskaya、A. Yu. Fedorov

  DOI：10.1134/s1070428016080078

  日期：2016.8

  Reaction of hydroxyl-containing heterocyclic colchicinoids with S-nucleophiles led to the formation of furanoallocolchicinoid sulfides in a high yield.