epolactaene tertiary butyl ester | 634589-47-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: epolactaene tertiary butyl ester
• 英文别名: (3E,5E,9E)-tert-butyl-2-ethylidene-11-(4-hydroxy-4-methyl-2-oxo-6-oxa-3-aza-bicyclo[3.1.0]hex-1-yl)-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate；tert-butyl (2E,3E,5E,9E)-2-ethylidene-11-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate
• CAS: 634589-47-2
• 化学式: C₂₄H₃₃NO₆
• 分子量: 431.529
• InChiKey: JNWXPFBGHSIYFC-SCMHSPARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  epolactaene tertiary butyl ester 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 、 三氟乙酸 作用下， 反应 4.0h， 生成 (3E,5E,9E)-2-Eth-(E)-ylidene-11-((1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-aza-bicyclo[3.1.0]hex-1-yl)-4,10-dimethyl-11-oxo-undeca-3,5,9-trienoic acid 11-amino-undecyl ester
  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：

  tert-butyl (2E,3E,5E,9E)-11-[(2R,3S)-2-carbamoyl-3-[(1S)-1-hydroxyethyl]oxiran-2-yl]-2-ethylidene-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate 在 pyridine-SO3 complex 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 以48%的产率得到epolactaene tertiary butyl ester
  参考文献：
  名称：

  Novel compound having antitumor activity and process for producing the same

  摘要：

  一个由一般式(I)表示的化合物：(I)其中R代表线性、支链或环烷基或芳基；一种生产该化合物的方法；以及含有该化合物作为活性成分的抗肿瘤剂。

  公开号：

  US20050209463A1

文献信息

• US7612213B2
  申请人：——

  公开号：US7612213B2

  公开（公告）日：2009-11-03
• Novel compound having antitumor activity and process for producing the same
  申请人：Osada Hiroyuki

  公开号：US20050209463A1

  公开（公告）日：2005-09-22

  A compound represented by the general formula (I): (I) wherein R represents linear, branched, or cyclic alkyl or aryl; a process for producing the compound; and an antitumor agent containing the compound as an active ingredient.

  一个由一般式(I)表示的化合物：(I)其中R代表线性、支链或环烷基或芳基；一种生产该化合物的方法；以及含有该化合物作为活性成分的抗肿瘤剂。
• Structure–activity relationships of epolactaene derivatives: structural requirements for inhibition of Hsp60 chaperone activity
  作者：Yoko Nagumo、Hideaki Kakeya、Junichiro Yamaguchi、Takao Uno、Mitsuru Shoji、Yujiro Hayashi、Hiroyuki Osada

  DOI：10.1016/j.bmcl.2004.06.054

  日期：2004.9

  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.