(3R,4R)-5-hydroxy-5-methyl-3-(2-methyl-2-undecenoyl)-3,4-epoxy-2-pyrrolidone | 762288-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (3R,4R)-5-hydroxy-5-methyl-3-(2-methyl-2-undecenoyl)-3,4-epoxy-2-pyrrolidone
• 英文别名: (1R,5R)-4-hydroxy-4-methyl-1-[(E)-2-methylundec-2-enoyl]-6-oxa-3-azabicyclo[3.1.0]hexan-2-one
• CAS: 762288-43-7
• 化学式: C₁₇H₂₇NO₄
• 分子量: 309.406
• InChiKey: GOFJLTCWAYYYKT-SHMBNMPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R)-5-hydroxy-5-methyl-3-(2-methyl-2-undecenoyl)-3,4-epoxy-2-pyrrolidone 在 palladium on activated charcoal 氢气 作用下， 以84%的产率得到(1R,5R)-4-Hydroxy-4-methyl-1-(2-methyl-undecanoyl)-6-oxa-3-aza-bicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Structure–activity relationships of epolactaene derivatives: structural requirements for inhibition of Hsp60 chaperone activity

  摘要：

  Epolactaene is a microbial metabolite isolated from the fungal strain Penicillium sp. It arrests the cell cycle at the G(0)/G(1), phase and induces the outgrowth of neurites in human neuroblastoma SH-SY5Y cells. In this communication, we report the structure-activity relationships (SARs) of new epolactaene derivatives, including those lacking the epoxylactam moiety and having various side chains. These derivatives were evaluated for their ability to inhibit the growth of human cancer cell lines. They were also analyzed for their ability to affect human heat shock protein 60 (Hsp60), which we have already identified as a protein that binds to epolactaene. We also identified the important structural framework of epolactaene/ETB (epolactaene tertiary butyl ester) for not only binding to Hsp60 but also inhibiting Hsp60 chaperone activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.054
• 作为产物：
  描述：

  壬醛 在 氟化铵 、 正丁基锂 、 pyridine-SO3 complex 、 三苯甲基氢过氧化物 、 potassium tert-butylate 、 silica gel 、 溶剂黄146 、 ethylenediamine Tetraacetic Acid 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (3R,4R)-5-hydroxy-5-methyl-3-(2-methyl-2-undecenoyl)-3,4-epoxy-2-pyrrolidone
  参考文献：
  名称：

  Structure–activity relationships of epolactaene derivatives: structural requirements for inhibition of Hsp60 chaperone activity

  摘要：

  Epolactaene is a microbial metabolite isolated from the fungal strain Penicillium sp. It arrests the cell cycle at the G(0)/G(1), phase and induces the outgrowth of neurites in human neuroblastoma SH-SY5Y cells. In this communication, we report the structure-activity relationships (SARs) of new epolactaene derivatives, including those lacking the epoxylactam moiety and having various side chains. These derivatives were evaluated for their ability to inhibit the growth of human cancer cell lines. They were also analyzed for their ability to affect human heat shock protein 60 (Hsp60), which we have already identified as a protein that binds to epolactaene. We also identified the important structural framework of epolactaene/ETB (epolactaene tertiary butyl ester) for not only binding to Hsp60 but also inhibiting Hsp60 chaperone activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.054

文献信息

• Determination by Asymmetric Total Synthesis of the Absolute Configuration of Lucilactaene, a Cell-Cycle Inhibitor in p53-Transfected Cancer Cells
  作者：Junichiro Yamaguchi、Hideaki Kakeya、Takao Uno、Mitsuru Shoji、Hiroyuki Osada、Yujiro Hayashi

  DOI：10.1002/anie.200500060

  日期：2005.5.13