[(1R,2E,6E,10S,11E,13S)-13-hydroxy-3,7,13-trimethyl-10-propan-2-ylcyclotetradeca-2,6,11-trien-1-yl] N-(2-chloroethyl)carbamate | 1009081-78-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1R,2E,6E,10S,11E,13S)-13-hydroxy-3,7,13-trimethyl-10-propan-2-ylcyclotetradeca-2,6,11-trien-1-yl] N-(2-chloroethyl)carbamate
• CAS: 1009081-78-0
• 化学式: C₂₃H₃₈ClNO₃
• 分子量: 412.013
• InChiKey: ASERFLMHCJBCPH-UOOYGCKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氯乙基异氰酸酯 、 (4E,8E,13E)-(1S,3R,12S)-12-Isopropyl-1,5,9-trimethyl-cyclotetradeca-4,8,13-triene-1,3-diol 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以52%的产率得到[(1R,2E,6E,10S,11E,13S)-13-hydroxy-3,7,13-trimethyl-10-propan-2-ylcyclotetradeca-2,6,11-trien-1-yl] N-(2-chloroethyl)carbamate
  参考文献：
  名称：

  Semisynthetic and Biotransformation Studies of (1S,2E,4S,6R,7E,11E)-2,7,11-Cembratriene-4,6-diol

  摘要：

  Tobacco-derived (1S,2E,4S,6R,7E,11E)-2,7,11-cembratriene-4,6-diol (1) and (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol (2) were first shown to display potential antitumor-promoting activity in the mid-1980s. However, very little is currently understood regarding the structural activity relationships of tobacco cembranoids. The aim of this present study was to explore anti proliferative activity of various derivatives of (1S,2E,4S,6R,7E,11E)-2,7,11-cembratriene-4,6-diol (1) using semisynthetic and biotransformation approaches. Derivatives of 1 include esterified, oxidized, halogenated, and nitrogen- and sulfur-containing compounds (3-17). Biotransformation of 1 using Mucor ramannianus ATCC 9628 and Cunninghamella elegans ATCC 7929 afforded the known 10S,11S-epoxy analogue of 1 (4) as the main metabolite. Biotransformation of the 6-O-acetyl analogue (3) using the marine symbiotic Bacillus megaterium strain MO31 afforded (1S,2E,4S,6R,7E,11E,10R)-2,7,11-cembratriene-4,6,10-triol (18). (1S,2E,4S,6R,7E,11E,13R)-2,7,11-cembratriene-4,6,13-triol-6-O-acetate (6), (1S,2E,4S,6R,7E,11E,13S)-2,7,11-cembratriene-4,6,13-triol-6-O-acetate (7), the rearranged alpha-ketol (1S,2E,4S,7Z,11E)-2,7,11-cembratrien-4-ol-6-one (11), and the secocembranoid 12 showed antiproliferative activity against highly malignant +SA mammary epithelial cells with an IC50 range of 15-30 mu M.

  DOI：

  10.1021/np0704351

文献信息

• Semisynthetic and Biotransformation Studies of (1<i>S</i>,2<i>E</i>,4<i>S</i>,6<i>R</i>,7<i>E</i>,11<i>E</i>)-2,7,11-Cembratriene-4,6-diol
  作者：Khalid A. El Sayed、Surat Laphookhieo、Muhammad Yousaf、Justin A. Prestridge、Amit B. Shirode、Vikram B. Wali、Paul W. Sylvester

  DOI：10.1021/np0704351

  日期：2008.1.1

  Tobacco-derived (1S,2E,4S,6R,7E,11E)-2,7,11-cembratriene-4,6-diol (1) and (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol (2) were first shown to display potential antitumor-promoting activity in the mid-1980s. However, very little is currently understood regarding the structural activity relationships of tobacco cembranoids. The aim of this present study was to explore anti proliferative activity of various derivatives of (1S,2E,4S,6R,7E,11E)-2,7,11-cembratriene-4,6-diol (1) using semisynthetic and biotransformation approaches. Derivatives of 1 include esterified, oxidized, halogenated, and nitrogen- and sulfur-containing compounds (3-17). Biotransformation of 1 using Mucor ramannianus ATCC 9628 and Cunninghamella elegans ATCC 7929 afforded the known 10S,11S-epoxy analogue of 1 (4) as the main metabolite. Biotransformation of the 6-O-acetyl analogue (3) using the marine symbiotic Bacillus megaterium strain MO31 afforded (1S,2E,4S,6R,7E,11E,10R)-2,7,11-cembratriene-4,6,10-triol (18). (1S,2E,4S,6R,7E,11E,13R)-2,7,11-cembratriene-4,6,13-triol-6-O-acetate (6), (1S,2E,4S,6R,7E,11E,13S)-2,7,11-cembratriene-4,6,13-triol-6-O-acetate (7), the rearranged alpha-ketol (1S,2E,4S,7Z,11E)-2,7,11-cembratrien-4-ol-6-one (11), and the secocembranoid 12 showed antiproliferative activity against highly malignant +SA mammary epithelial cells with an IC50 range of 15-30 mu M.