((1aR,7aS,10aS,10bS,E)-1a-methyl-8-methylene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-decahydrooxireno[2',3':9,10]-cyclodeca[1,2-b]furan-5-yl)-methyl(2-morpholinoethyl)carbamate | 1619942-34-5

• 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: ((1aR,7aS,10aS,10bS,E)-1a-methyl-8-methylene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-decahydrooxireno[2',3':9,10]-cyclodeca[1,2-b]furan-5-yl)-methyl(2-morpholinoethyl)carbamate
• 英文别名: [(1S,2S,4R,7E,11S)-4-methyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-8-yl]methyl N-(2-morpholin-4-ylethyl)carbamate
• CAS: 1619942-34-5
• 化学式: C₂₂H₃₂N₂O₆
• 分子量: 420.506
• InChiKey: SPZJKUBWCKFMLK-YUPLBTLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  89.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  melampomagnolide B 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 ((1aR,7aS,10aS,10bS,E)-1a-methyl-8-methylene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-decahydrooxireno[2',3':9,10]-cyclodeca[1,2-b]furan-5-yl)-methyl(2-morpholinoethyl)carbamate
  参考文献：
  名称：

  Anti-cancer activity of carbamate derivatives of melampomagnolide B

  摘要：

  Melampomagnolide B (MMB) is a natural sesquiterpene structurally related to parthenolide (PTL). We have shown that MMB exhibits anti-leukemic properties similar to PTL. Unlike PTL, the presence of a primary hydroxyl group in the MMB molecule allows the opportunity for examining the biological activity of a variety of conjugated analogs of MMB. We have now synthesized a series of carbamate analogs of MMB and evaluated these derivatives for anti-cancer activity against a panel of sixty human cancer cell lines. Analogs 6a and 6e exhibited promising anti-leukemic activity against human leukemia cell line CCRF-CEM with GI(50) values of 680 and 620 nM, respectively. Analog 6a also showed GI(50) values of 1.98 and 1.38 mu M respectively, against RPMI-8226 and SR leukemia cell lines and GI(50) values of 460 and 570 nM against MDA-MB-435 melanoma and MDA-MB-468 breast cancer cell lines, respectively. Analog 6e had GI(50) values of 650 and 900 nM against HOP-92 non-small cell lung and RXF 393 renal cancer cell lines. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.05.059

文献信息

• MELAMPOMAGNOLIDE B DERIVATIVES
  申请人：Janganati Venumadhav

  公开号：US20150133444A1

  公开（公告）日：2015-05-14

  The present disclosure provides derivatives of melampomagnolide B (MMB), including carbonates, carbamates, and thiocarbamates. The derivatives may be synthesized via an MMB triazole intermediate. These derivatives are useful for treating cancer in humans.

  本公开提供了槲皮素B（MMB）的衍生物，包括碳酸酯、氨基甲酸酯和硫代氨基甲酸酯。这些衍生物可以通过MMB三唑中间体合成。这些衍生物对于治疗人类癌症是有用的。
• US9469650B2
  申请人：——

  公开号：US9469650B2

  公开（公告）日：2016-10-18
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  公开号：US9487536B2

  公开（公告）日：2016-11-08
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  申请人：——

  公开号：US9908892B2

  公开（公告）日：2018-03-06
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  申请人：——

  公开号：US9920063B2

  公开（公告）日：2018-03-20