2-crotonyloxymethyl-2-cyclopentenone | 106281-46-3

• 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: 2-crotonyloxymethyl-2-cyclopentenone
• 英文别名: (5-Oxocyclopent-1-en-1-yl)methyl but-2-enoate；(5-oxocyclopenten-1-yl)methyl but-2-enoate
• CAS: 106281-46-3
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: VWBLMJQSBXLUNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基甲基-2-环戊酮 、 巴豆酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以71%的产率得到2-crotonyloxymethyl-2-cyclopentenone
  参考文献：
  名称：

  Molecular Basis of the Antitumor Activities of 2-Crotonyloxymethyl-2-cycloalkenones

  摘要：

  The antitumor activity of 2 crotonyloxymethyl-2-cyclohexenone (COMC-6) is not the result of the GSH conjugate (GSMC-6) formed inside tumor cells, as the diethyl ester prodrug form of GSMC-6 displays little antitumor activity with B16 melanotic melanoma in vitro IC50 > 460 muM) versus COMC-6 (IC50 0.041 muM) and its five- and seven-membered ring homologues. Antitumor activity probably results from a reactive intermediate that forms during conjugation of the COMCs with intracellular GSH.

  DOI：

  10.1021/jm0203027

文献信息

• Molecular Basis of the Antitumor Activities of 2-Crotonyloxymethyl-2-cycloalkenones
  作者：Erin Joseph、Julie L. Eiseman、Diana S. Hamilton、Haibo Wang、Heekyung Tak、Zhebo Ding、Bruce Ganem、Donald J. Creighton

  DOI：10.1021/jm0203027

  日期：2003.1.1

  The antitumor activity of 2 crotonyloxymethyl-2-cyclohexenone (COMC-6) is not the result of the GSH conjugate (GSMC-6) formed inside tumor cells, as the diethyl ester prodrug form of GSMC-6 displays little antitumor activity with B16 melanotic melanoma in vitro IC50 > 460 muM) versus COMC-6 (IC50 0.041 muM) and its five- and seven-membered ring homologues. Antitumor activity probably results from a reactive intermediate that forms during conjugation of the COMCs with intracellular GSH.