butane-1,4-diylbis(((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)dicarbonate

• 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: butane-1,4-diylbis(((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)dicarbonate
• 英文别名: 4-[[(1S,2S,4R,7E,11S)-4-methyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-8-yl]methoxycarbonyloxy]butyl [(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 carbonate
• 化学式: C₃₆H₄₆O₁₂
• 分子量: 670.754
• InChiKey: FTFAOGWLIAOJEQ-IPZJNBEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  12

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 17.0h， 生成 butane-1,4-diylbis(((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)dicarbonate
  参考文献：
  名称：

  [EN] MELAMPOMAGNOLIDE B DIMERS
  [FR] DIMÈRES DE MÉLAMPOMAGNOLIDE B

  摘要：

  本公开提供了美拉波木内酯B（MMB）的二聚体，包括MMB的氨基甲酸酯、碳酸酯、琥珀酰胺、酯和羧酰胺二聚体。这些衍生物对于治疗人类癌症特别有用，尤其是治疗白血病，包括急性髓性白血病（AML）。一种包含如下式（1）的化合物：其中：Z独立地选自由CH2、O、C（O）和CH组成的群，当Z为CH时，Z通过双键连接到Y，而Y为N。

  公开号：

  WO2016090166A1

文献信息

• [EN] MELAMPOMAGNOLIDE B DIMERS<br/>[FR] DIMÈRES DE MÉLAMPOMAGNOLIDE B
  申请人：UNIV ARKANSAS

  公开号：WO2016090166A1

  公开（公告）日：2016-06-09

  The present disclosure provides dimers of melampomagnolide B (MMB), including carbamate, carbonate, succinic amide, ester and carboxamide dimers of MMB. These derivatives are useful for treating cancer in humans, in particular in treating leukemia, including acute myelogenous leukemia (AML). A compound comprising Formula (1 ) wherein: Z is independently selected from the group consisting of CH2, O, C(O), and CH, wherein when Z is CH, Z is connected to Y via a double bond and Y is N.

  本公开提供了美拉波木内酯B（MMB）的二聚体，包括MMB的氨基甲酸酯、碳酸酯、琥珀酰胺、酯和羧酰胺二聚体。这些衍生物对于治疗人类癌症特别有用，尤其是治疗白血病，包括急性髓性白血病（AML）。一种包含如下式（1）的化合物：其中：Z独立地选自由CH2、O、C（O）和CH组成的群，当Z为CH时，Z通过双键连接到Y，而Y为N。
• MELAMPOMAGNOLIDE B DIMERS
  申请人：BioVentures, LLC

  公开号：US20170362254A1

  公开（公告）日：2017-12-21

  The present disclosure provides dimers of melampomagnolide B (MMB), including carbamate, carbonate, succinic amide, ester and carboxamide dimers of MMB. These derivatives are useful for treating cancer in humans, in particular in treating leukemia, including acute myelogenous leukemia (AML). A compound comprising Formula (1) wherein: Z is independently selected from the group consisting of CH2, O, C(O), and CH, wherein when Z is CH, Z is connected to Y via a double bond and Y is N.
• US9981990B2
  申请人：——

  公开号：US9981990B2

  公开（公告）日：2018-05-29
• Dimers of Melampomagnolide B Exhibit Potent Anticancer Activity against Hematological and Solid Tumor Cells
  作者：Venumadhav Janganati、Jessica Ponder、Craig T. Jordan、Michael J. Borrelli、Narsimha Reddy Penthala、Peter A. Crooks

  DOI：10.1021/acs.jmedchem.5b01187

  日期：2015.11.25

  Novel carbamate (7a-7h) and carbonate (7i, 7j, and 8) dimers of melampomagnolide B have been synthesized by reaction of the melampomagnolide-B-triazole carbamate synthon 6 with various terminal diamino- and dihydroxyalkanes. Dimeric carbamate products 7b, 7c, and 7f exhibited potent growth inhibition (GI(50) = 0.16-0.99 mu M) against the majority of cell lines in the NCI panel of 60 human hematological and solid tumor cell lines. Compound 7f and 8 exhibited anticancer activity that was 300-fold and 1 x 10(6)-fold more cytotoxic that DMAPT, respectively, at a concentration of 10 mu M against rat 9L-SF gliosarcoma cells. Compounds 7a-7j and 8 were also screened against M9-ENL1 and acute myelogeous leukemia (AML) primary cell lines and exhibited 2- to 10-fold more potent antileukemic activity against M9-ENL1 cells (EC50 = 0.57-2.90 mu M) when compared to parthenolide (EC50 = 6.0) and showed potent antileukemic activity against five primary AML cell lines (EC50 = 0.76-7.3 mu M).