(1S,2R,6S,9S,10S)-10-hydroxy-1,9-dimethyl-5-methylidene-3,14-dioxatricyclo[8.4.0.02,6]tetradec-11-ene-4,13-dione | 1186473-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (1S,2R,6S,9S,10S)-10-hydroxy-1,9-dimethyl-5-methylidene-3,14-dioxatricyclo[8.4.0.02,6]tetradec-11-ene-4,13-dione
• CAS: 1186473-39-1
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: HEVWMFVJZUUZKV-JISBIHODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,6S,9S,10S)-10-hydroxy-1,9-dimethyl-5-methylidene-3,14-dioxatricyclo[8.4.0.02,6]tetradec-11-ene-4,13-dione 在 三氟乙酸 作用下， 生成 (3aS,6S,7S,8S,8aR)-8-hydroxy-6,8-dimethyl-3-methylidenespiro[4,5,6,8a-tetrahydro-3aH-cyclohepta[b]furan-7,5'-furan]-2,2'-dione
  参考文献：
  名称：

  Psilostachyin, acetylated pseudoguaianolides and their analogues: Preparation and evaluation of their anti-inflammatory potential

  摘要：

  Naturally occurring acetylated pseudoguaianolides and psilostachyin including their analogues were synthesized. The structure of semi-synthetic psilostachyin was also confirmed by X-ray crystallography. The anti-inflammatory potential of all the derivatives has been evaluated through in vitro expression of TNF-alpha, IL-1 beta and IL-6 in murine neutrophils. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.037
• 作为产物：
  描述：

  银胶菊宁 在 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 氯仿 为溶剂， 以70%的产率得到(1S,2R,6S,9S,10S)-10-hydroxy-1,9-dimethyl-5-methylidene-3,14-dioxatricyclo[8.4.0.02,6]tetradec-11-ene-4,13-dione
  参考文献：
  名称：

  Structure–activity relationship (SAR) of parthenin analogues with pro-apoptotic activity: Development of novel anti-cancer leads

  摘要：

  Analogues of parthenin were synthesized by substitutions at different reaction centres to establish a structure-activity relationship (SAR). Some of the molecules have displayed significant cytotoxicity in human cervical carcinoma (HeLa) and human myeloid leukemia (HL-60) cells. A few of the compounds also induced apoptosis in HL-60 cells measured in terms of sub-Go/G1 DNA fraction. Also one of the lead molecules has been shown to be the inhibitor of both telomerase and topoisomerase-II. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.089

文献信息

• Structure–activity relationship (SAR) of parthenin analogues with pro-apoptotic activity: Development of novel anti-cancer leads
  作者：Bhahwal Ali Shah、Rajbir Kaur、Pankaj Gupta、Ajay Kumar、Vijay Kumar Sethi、Samar Singh Andotra、Jaswant Singh、Ajit Kumar Saxena、Subhash Chandra Taneja

  DOI：10.1016/j.bmcl.2009.05.089

  日期：2009.8

  Analogues of parthenin were synthesized by substitutions at different reaction centres to establish a structure-activity relationship (SAR). Some of the molecules have displayed significant cytotoxicity in human cervical carcinoma (HeLa) and human myeloid leukemia (HL-60) cells. A few of the compounds also induced apoptosis in HL-60 cells measured in terms of sub-Go/G1 DNA fraction. Also one of the lead molecules has been shown to be the inhibitor of both telomerase and topoisomerase-II. (C) 2009 Elsevier Ltd. All rights reserved.
• Psilostachyin, acetylated pseudoguaianolides and their analogues: Preparation and evaluation of their anti-inflammatory potential
  作者：Renu Chib、Bhahwal Ali Shah、Naveen Anand、Anjali Pandey、Kamini Kapoor、Sarang Bani、Vivek K. Gupta、Rajnikant、Vijay K. Sethi、Subhash Chandra Taneja

  DOI：10.1016/j.bmcl.2011.06.037

  日期：2011.8

  Naturally occurring acetylated pseudoguaianolides and psilostachyin including their analogues were synthesized. The structure of semi-synthetic psilostachyin was also confirmed by X-ray crystallography. The anti-inflammatory potential of all the derivatives has been evaluated through in vitro expression of TNF-alpha, IL-1 beta and IL-6 in murine neutrophils. (C) 2011 Elsevier Ltd. All rights reserved.