Methyl 3-benzyl-2-methyl-5-oxo-2-phenyloxolane-3-carboxylate | 1349703-77-0

• 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: Methyl 3-benzyl-2-methyl-5-oxo-2-phenyloxolane-3-carboxylate
• CAS: 1349703-77-0
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: MVFDAGHVAFZJTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  溴苯 、 衣康酸二甲酯 、 苯乙酮 在 cobalt(II) bromide 、 锌 作用下， 以 乙腈 为溶剂， 以82%的产率得到Methyl 3-benzyl-2-methyl-5-oxo-2-phenyloxolane-3-carboxylate
  参考文献：
  名称：

  Synthesis and cytotoxic evaluation of novel paraconic acid analogs

  摘要：

  A novel class of 2,3-tri- and tetrasubstituted gamma-butyrolactones analogous to paraconic acids has been synthesized in one step using a straightforward three-component reaction among aryl bromides, dimethyl itaconate and carbonyl compounds. The in vitro cytotoxic activity of representative compounds has been evaluated against a panel of human cancer cell lines (KB, HCT116, MCF7, HL60). While most molecules exhibit a low to moderate background activity on both KB and HL60 cancer cell lines, one compound shows increased antiproliferative activities against both cell lines with IC50 values in the 10(-7)-10(-6) mol/L range. An extended evaluation indicated that this compound also inhibits PC3, SK-OV3, MCF7R and HL60R cell growth in the same fashion. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.092

文献信息

• Synthesis and cytotoxic evaluation of novel paraconic acid analogs
  作者：Camille Le Floch、Erwan Le Gall、Eric Léonel、Thierry Martens、Thierry Cresteil

  DOI：10.1016/j.bmcl.2011.09.092

  日期：2011.12

  A novel class of 2,3-tri- and tetrasubstituted gamma-butyrolactones analogous to paraconic acids has been synthesized in one step using a straightforward three-component reaction among aryl bromides, dimethyl itaconate and carbonyl compounds. The in vitro cytotoxic activity of representative compounds has been evaluated against a panel of human cancer cell lines (KB, HCT116, MCF7, HL60). While most molecules exhibit a low to moderate background activity on both KB and HL60 cancer cell lines, one compound shows increased antiproliferative activities against both cell lines with IC50 values in the 10(-7)-10(-6) mol/L range. An extended evaluation indicated that this compound also inhibits PC3, SK-OV3, MCF7R and HL60R cell growth in the same fashion. (C) 2011 Elsevier Ltd. All rights reserved.