[(1R,2E,6S,7S,10S,11E,13S)-6,13-dihydroxy-3,7,13-trimethyl-10-propan-2-yl-7-thiocyanatocyclotetradeca-2,11-dien-1-yl] acetate | 1009081-72-4

• 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,6S,7S,10S,11E,13S)-6,13-dihydroxy-3,7,13-trimethyl-10-propan-2-yl-7-thiocyanatocyclotetradeca-2,11-dien-1-yl] acetate
• CAS: 1009081-72-4
• 化学式: C₂₃H₃₇NO₄S
• 分子量: 423.617
• InChiKey: LMDUSAACXMMYTD-SRHANZHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  硫氰酸铵 、 (1S,2E,4S,6R,7E,11S,12S)-2,7-cembradiene-11,12-epoxy-4,6-diol-6-O-acetate 在 三氯化锑 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以13.7%的产率得到[(3aS,6S,7E,9S,11R,12E,15aS)-9-hydroxy-2-imino-3a,9,13-trimethyl-6-propan-2-yl-4,5,6,10,11,14,15,15a-octahydrocyclotetradeca[d][1,3]oxathiol-11-yl] acetate
  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.