[(1R,2E,6E,10S,11E,13R)-13-hydroxy-3,7,13-trimethyl-10-propan-2-ylcyclotetradeca-2,6,11-trien-1-yl] N-(2-chloroethyl)carbamate | 1026661-38-0

• 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,13R)-13-hydroxy-3,7,13-trimethyl-10-propan-2-ylcyclotetradeca-2,6,11-trien-1-yl] N-(2-chloroethyl)carbamate
• CAS: 1026661-38-0
• 化学式: C₂₃H₃₈ClNO₃
• 分子量: 412.013
• InChiKey: ASERFLMHCJBCPH-OJLKJCBCSA-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 、 (1S,2E,4R,6R,7E,11E)-cembra-2,7,11-triene-4,6-diol 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以63%的产率得到[(1R,2E,6E,10S,11E,13R)-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：

  Biocatalytic and semisynthetic optimization of the anti-invasive tobacco (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol

  摘要：

  Tobacco cembranoids were reported to inhibit tumorigenesis. Biocatalysis of (1S,2E,4R,6R,7E, 11E)-2,7,11-cembratriene4,6-diol (1) using the symbiotic Bacillus sp. NC5, Bacillus sp. NK8, and Bacillus sp. NK7, isolated from the Red Sea sponge Negombata magnifica, afforded two new and four known hydroxylated metabolites 3-8. The use of symbiotic marine bacteria as biocatalysts for bioactive natural product scaffolds is very rare. Cembranoid 1 carbamate analogs 9-11 were prepared by its reaction with corresponding isocyanates. Cembranoid 1 and its bioconversion and carabamate products show anti-invasive activity against the human highly metastatic prostate PC-3M cancer cell line at 10-50 nM doses in Matrigel assay. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.056

文献信息

• Biocatalytic and semisynthetic optimization of the anti-invasive tobacco (1S,2E,4R,6R,7E,11E)-2,7,11-cembratriene-4,6-diol
  作者：Khalid A. El Sayed、Surat Laphookhieo、Hany N. Baraka、Muhammad Yousaf、Anne Hebert、Danielle Bagaley、Frederick A. Rainey、A. Muralidharan、Shibu Thomas、Girish V. Shah

  DOI：10.1016/j.bmc.2007.12.056

  日期：2008.3.15

  Tobacco cembranoids were reported to inhibit tumorigenesis. Biocatalysis of (1S,2E,4R,6R,7E, 11E)-2,7,11-cembratriene4,6-diol (1) using the symbiotic Bacillus sp. NC5, Bacillus sp. NK8, and Bacillus sp. NK7, isolated from the Red Sea sponge Negombata magnifica, afforded two new and four known hydroxylated metabolites 3-8. The use of symbiotic marine bacteria as biocatalysts for bioactive natural product scaffolds is very rare. Cembranoid 1 carbamate analogs 9-11 were prepared by its reaction with corresponding isocyanates. Cembranoid 1 and its bioconversion and carabamate products show anti-invasive activity against the human highly metastatic prostate PC-3M cancer cell line at 10-50 nM doses in Matrigel assay. (C) 2008 Elsevier Ltd. All rights reserved.