(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-6-methylidene-3-[(2-methylphenyl)sulfanylmethyl]-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione | 248584-39-6

• 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: (3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-6-methylidene-3-[(2-methylphenyl)sulfanylmethyl]-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione
• CAS: 248584-39-6
• 化学式: C₂₂H₂₆O₄S
• 分子量: 386.512
• InChiKey: DZVCSSRSWOPGQQ-HIZKJQGSSA-N

物化性质

• 沸点：
  590.6±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-6-methylidene-3-[(2-methylphenyl)sulfanylmethyl]-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione 在 phosphate buffer 、 双氧水 作用下， 以 甲醇 为溶剂， 生成 grosheimin 、 2-甲基苯磺酸
  参考文献：
  名称：

  Phenylthio-derivatives of α-methylene-γ-lactones as pro-drugs of cytotoxic agents§

  摘要：

  A series of substituted phenylthio-derivatives of grosheimin (1), a natural cytotoxic guaianolide, were investigated with the aim of providing insight into their mechanism of action as cytotoxic agents against KB cell lines. Hydrolysis data, kinetics, in the presence and in the absence of H2O2, and the valuation of lipophilicity were correlated with cytotoxicity values and with Hammett-sigma-values of substituents (R) at the thiophenol ring. These compounds behave as 'pro-drugs' which release the cytotoxic agent grosheimin by sulphur-oxidation promoted by H2O2 and subsequent retro-elimination which depends on the nature and position of the R substituent. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80100-7
• 作为产物：
  描述：

  grosheimin 、 2-巯基甲苯 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以77%的产率得到(3S,3aR,4S,6aR,9S,9aR,9bR)-4-hydroxy-9-methyl-6-methylidene-3-[(2-methylphenyl)sulfanylmethyl]-3a,4,5,6a,7,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2,8-dione
  参考文献：
  名称：

  Phenylthio-derivatives of α-methylene-γ-lactones as pro-drugs of cytotoxic agents§

  摘要：

  A series of substituted phenylthio-derivatives of grosheimin (1), a natural cytotoxic guaianolide, were investigated with the aim of providing insight into their mechanism of action as cytotoxic agents against KB cell lines. Hydrolysis data, kinetics, in the presence and in the absence of H2O2, and the valuation of lipophilicity were correlated with cytotoxicity values and with Hammett-sigma-values of substituents (R) at the thiophenol ring. These compounds behave as 'pro-drugs' which release the cytotoxic agent grosheimin by sulphur-oxidation promoted by H2O2 and subsequent retro-elimination which depends on the nature and position of the R substituent. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80100-7

文献信息

• Phenylthio-derivatives of α-methylene-γ-lactones as pro-drugs of cytotoxic agents§
  作者：Giuseppe Fardella、Paolo Barbetti、Giuliano Grandolini、Ione Chiappini、Valeria Ambrogi、Vito Scarcia、Ariella Furlani Candiani

  DOI：10.1016/s0223-5234(99)80100-7

  日期：1999.6

  A series of substituted phenylthio-derivatives of grosheimin (1), a natural cytotoxic guaianolide, were investigated with the aim of providing insight into their mechanism of action as cytotoxic agents against KB cell lines. Hydrolysis data, kinetics, in the presence and in the absence of H2O2, and the valuation of lipophilicity were correlated with cytotoxicity values and with Hammett-sigma-values of substituents (R) at the thiophenol ring. These compounds behave as 'pro-drugs' which release the cytotoxic agent grosheimin by sulphur-oxidation promoted by H2O2 and subsequent retro-elimination which depends on the nature and position of the R substituent. (C) Elsevier, Paris.