N-((1S)-2''-(8-(metoxycarbonyl)octyl)-1',2',3'-trimetoxy-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''-(8-(metoxycarbonyl)octyl)-1',2',3'-trimetoxy-6,7-dihydro-1H-benzo[5',6':5,4]cyclohepta[3,2-f]benzofuran-1-yl)acetamide
• 英文别名: methyl 9-[(10S)-10-acetamido-3,4,5-trimethoxy-14-oxatetracyclo[9.7.0.02,7.013,17]octadeca-1(11),2,4,6,12,15,17-heptaen-15-yl]nonanoate
• 化学式: C₃₂H₄₁NO₇
• 分子量: 551.68
• InChiKey: QBWYWTCBXWRXGH-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  96.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 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 hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 生成 N-((1S)-2''-(8-(metoxycarbonyl)octyl)-1',2',3'-trimetoxy-6,7-dihydro-1H-benzo[5',6':5,4]cyclohepta[3,2-f]benzofuran-1-yl)acetamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Furanoallocolchicinoids

  摘要：

  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.

  DOI：

  10.1021/jm501678w

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.