(2aR,3R,4S,5aS,5bS,7aS,8S,11aS,12aS)-3-((2S,3R,6R)-3-acetoxy-7-hydroxy-6-methyl-5-methylene-4-oxoheptan-2-yl)-9-(hydroxyimino)-2a,5a,8-trimethyl-2,2a,3,4,5,5a,5b,6,7,7a,8,9-dodecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-4-yl acetate | 1356964-35-6

• 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: (2aR,3R,4S,5aS,5bS,7aS,8S,11aS,12aS)-3-((2S,3R,6R)-3-acetoxy-7-hydroxy-6-methyl-5-methylene-4-oxoheptan-2-yl)-9-(hydroxyimino)-2a,5a,8-trimethyl-2,2a,3,4,5,5a,5b,6,7,7a,8,9-dodecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-4-yl acetate
• CAS: 1356964-35-6
• 化学式: C₃₄H₄₉NO₇
• 分子量: 583.766
• InChiKey: FZYWAYGWHYVVDK-QDNFKKIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  122.49
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  neoboutomellerone 在 盐酸羟胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 20.0h， 以17%的产率得到(2aR,3R,4S,5aS,5bS,7aS,8S,11aS,12aS)-3-((2S,3R,6R)-3-acetoxy-7-hydroxy-6-methyl-5-methylene-4-oxoheptan-2-yl)-9-(hydroxyimino)-2a,5a,8-trimethyl-2,2a,3,4,5,5a,5b,6,7,7a,8,9-dodecahydro-1H,12H-cyclopenta[a]cyclopropa[e]phenanthren-4-yl acetate
  参考文献：
  名称：

  Semisynthetic neoboutomellerone derivatives as ubiquitin-proteasome pathway inhibitors

  摘要：

  The interesting pharmacological properties of neoboutomellerones 1 and 2 were the basis for the assembly of a small library of analogues consisting of natural products isolated from the plant Neoboutonia melleri and of semisynthetic derivatives. As the two enone systems (C23-C24a and C1-C3) and the two hydroxyls groups (C22 and C26) of neoboutomellerones are required for activity, modifications were focused on these functional groups. Biological evaluation by using a cellular assay for proteasome activity provided clues regarding the mechanism of action of these natural products and synthetic derivatives. Certain neoboutomellerone derivatives inhibited the proliferation of human WM-266-4 melanoma tumor cells at submicromolar concentration and warrant evaluation as anticancer agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.066