3-<1-(4-chlorophenyl)-2-nitro-ethyl>-perhydro-3,3a,6-trihydroxy-furo<3,2-b>furan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 3-<1-(4-chlorophenyl)-2-nitro-ethyl>-perhydro-3,3a,6-trihydroxy-furo<3,2-b>furan-2-one
• 英文别名: (3S,3aR,6S,6aS)-6-[1-(4-chlorophenyl)-2-nitroethyl]-3,6,6a-trihydroxy-3,3a-dihydro-2H-furo[3,2-b]furan-5-one
• 化学式: C₁₄H₁₄ClNO₈
• 分子量: 359.72
• InChiKey: QMKFYBFLRUQGKY-RZZUOMTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-nitro-2-(4-chlorophenyl)ethylene 、 维生素 C 以 乙醇 、 水 为溶剂， 反应 120.0h， 以81%的产率得到3-<1-(4-chlorophenyl)-2-nitro-ethyl>-perhydro-3,3a,6-trihydroxy-furo<3,2-b>furan-2-one
  参考文献：
  名称：

  Schmidt; Eger, Pharmazie, 1996, vol. 51, # 1, p. 11 - 16

  摘要：

  DOI：

文献信息

• Michael adducts of ascorbic acid as inhibitors of protein phosphatase 2A and inducers of apoptosis
  作者：A.R. Fathi、A. Krautheim、S. Kaap、K. Eger、H.J. Steinfelder

  DOI：10.1016/s0960-894x(00)00294-8

  日期：2000.7

  Michael adducts of ascorbic acid with alpha,beta-unsaturated carbonyl compounds have been shown to be potent inhibitors of protein phosphatase 1 (PPI) without affecting cell viability at the respective concentrations. Here we were able to show that higher concentrations can partially inhibit PP2A activity and concomitantly induce apoptotic cell death. A nitrostyrene adduct of ascorbic acid proved to be a more potent and effective inhibitor of PP2A as well as a stronger inducer of apoptosis. These adducts only slightly lost their cytotoxic potential in multidrug resistant cells that were 10-fold less sensitive to apoptosis induction by okadaic acid and vinblastine. (C) 2000 Elsevier Science Ltd. All rights reserved.