(4S)-11(13)-carabren-8β,12-olide-4-O-(S)-MTPA ester | 1268269-96-0

• 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: (4S)-11(13)-carabren-8β,12-olide-4-O-(S)-MTPA ester
• CAS: 1268269-96-0
• 化学式: C₂₅H₂₉F₃O₅
• 分子量: 466.497
• InChiKey: RTQDKZNPNQURSR-QBGAVBSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  carabrol 、 (S)-(-)-α-甲氧基-α-(三氟甲基)苯乙酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以3.5 mg的产率得到(4S)-11(13)-carabren-8β,12-olide-4-O-(S)-MTPA ester
  参考文献：
  名称：

  Antiproliferative and apoptotic sesquiterpene lactones from Carpesium faberi

  摘要：

  Four new (1-4) and 13 known (5-17) sesquiterpene lactones along with two known diterpenes (18, 19) were isolated from the whole plant of Carpesium faberi. The new structures were elucidated by means of spectroscopic techniques and some chemical transformations to be pseudoguaian-1 alpha(H)-8 alpha,12-olide-4 beta-O-beta-D-glucopyranoside (1), 4 beta,10 alpha-dihydroxy-5 alpha(H)-1,11(13)-guaidien-8 alpha,12-olide (2), 4 beta,10 beta-dihydroxy-5 alpha(H)-1, 11(13)-guaidien-8 beta,12-olide (3), and (4S)-acetyloxyl-11(13)-carabren-8 beta,12-olide (4). All isolates were tested against MCF-7 human breast cancer cells using the MTT assay. Among them, the sesquiterpene lactones (except tomentosin 17) possessing an alpha-methylene-gamma-lactone moiety were found to have in vitro antiproliferative activities, with IC50 values of 3.0-38.8 mu g/mL. The effects of four selected sesquiterpene lactones (guaianolide 2, carabranolide 4, pseudoguaianolide 9, eudesmanolide 13) on the cell cycle were examined using flow cytometry (FCM). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.138