Ochratoxin A methyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 赭曲霉毒素及相关物质
• 英文名称: Ochratoxin A methyl ester
• 英文别名: methyl (2R)-2-[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl)amino]-3-phenylpropanoate
• 化学式: C₂₁H₂₀ClNO₆
• 分子量: 417.846
• InChiKey: IHPSAIGCKPYNDR-WVQRXBFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  101.93
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Ochratoxin A methyl ester 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 14.0h， 生成 (3S,14R)-ochratoxin A 、 ochratoxin A
  参考文献：
  名称：

  Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers

  摘要：

  The mycotoxin ochratoxin A is a potent inhibitor of the protein biosynthesis and known to be cytotoxic in nanomolar concentrations. In order to investigate the relationship between stereochemistry and cytotoxicity of this compound, all four ochratoxin A stereoisomers have been synthesized. Using the liver cell line Hep G2, the compounds were tested for cytotoxic and apoptotic potential. It could be shown, that the L-configuration of the phenylalanine moiety of the molecule is mostly responsible for the high cytotoxicity of ochratoxin A while the stereocenter at the dihydroisocoumarine structure is of less importance. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.050
• 作为产物：
  描述：

  1H-2-苯并吡喃-7-羧基LIC酸,5-氯-3,4-二氢-8-羟基-3-甲基-1-氧代 、 D-苯丙氨酸甲酯盐酸盐 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 Ochratoxin A methyl ester
  参考文献：
  名称：

  Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers

  摘要：

  The mycotoxin ochratoxin A is a potent inhibitor of the protein biosynthesis and known to be cytotoxic in nanomolar concentrations. In order to investigate the relationship between stereochemistry and cytotoxicity of this compound, all four ochratoxin A stereoisomers have been synthesized. Using the liver cell line Hep G2, the compounds were tested for cytotoxic and apoptotic potential. It could be shown, that the L-configuration of the phenylalanine moiety of the molecule is mostly responsible for the high cytotoxicity of ochratoxin A while the stereocenter at the dihydroisocoumarine structure is of less importance. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.050

文献信息

• Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers
  作者：Benedikt Cramer、Henning Harrer、Kazuhiko Nakamura、Daisuke Uemura、Hans-Ulrich Humpf

  DOI：10.1016/j.bmc.2009.10.050

  日期：2010.1

  The mycotoxin ochratoxin A is a potent inhibitor of the protein biosynthesis and known to be cytotoxic in nanomolar concentrations. In order to investigate the relationship between stereochemistry and cytotoxicity of this compound, all four ochratoxin A stereoisomers have been synthesized. Using the liver cell line Hep G2, the compounds were tested for cytotoxic and apoptotic potential. It could be shown, that the L-configuration of the phenylalanine moiety of the molecule is mostly responsible for the high cytotoxicity of ochratoxin A while the stereocenter at the dihydroisocoumarine structure is of less importance. (C) 2009 Elsevier Ltd. All rights reserved.