(3R)-(+)-methyl-N-(2',4'-difluorophenyl)succinimide | 1451750-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R)-(+)-methyl-N-(2',4'-difluorophenyl)succinimide
• 英文别名: (3R)-1-(2,4-difluorophenyl)-3-methyl-pyrrolidine-2,5-dione；(3R)-1-(2,4-difluorophenyl)-3-methylpyrrolidine-2,5-dione
• CAS: 1451750-83-6
• 化学式: C₁₁H₉F₂NO₂
• 分子量: 225.195
• InChiKey: OYQAFFFPKOYHMG-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-methyl-N-(2',4'-difluorophenyl)maleimide 在 Aspergillus Fumigatus ATCC 26934 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 以99%的产率得到
  参考文献：
  名称：

  Effects of Chirality on the Antifungal Potency of Methylated Succinimides Obtained by Aspergillus fumigatus Biotransformations. Comparison with Racemic Ones

  摘要：

  利用烟曲霉菌对马来酰亚胺进行生物转化，制备了 18 种 (3R) 和 (3R,4R) -N-苯基、N-苯基烷基和 N-芳基丁二酰亚胺，具有很高的对映选择性。这一环保、清洁、经济的过程是通过全细胞真菌生物转化方法实现的。相应的 18 种外消旋琥珀酰亚胺是通过合成方法制备的。外消旋琥珀酰亚胺和手性琥珀酰亚胺同时通过 CLSI 的微流稀释法对一组具有临床重要性的人类机会致病真菌进行了测试。手性琥珀酰亚胺的抗真菌活性高于相应的外消旋琥珀酰亚胺，其活性差异已通过统计方法确定。开发手性药物的瓶颈在于如何通过低成本程序获得高对映体过量的药物。本文介绍的结果实现了这两个目标，为开发不对称琥珀酰亚胺作为新的抗真菌药物开辟了一条途径。

  DOI：

  10.3390/molecules18055669

文献信息

• Effects of Chirality on the Antifungal Potency of Methylated Succinimides Obtained by Aspergillus fumigatus Biotransformations. Comparison with Racemic Ones
  作者：Maximiliano Sortino、Agustina Postigo、Susana Zacchino

  DOI：10.3390/molecules18055669

  日期：——

  Eighteen (3R) and (3R,4R)-N-phenyl-, N-phenylalkyl and N-arylsuccinimides were prepared with high enantioselectivity by biotransformation of maleimides with A. fumigatus. This environmentally friendly, clean and economical procedure was performed by the whole-cell fungal bioconversion methodology. Their corresponding eighteen racemic succinimides were prepared instead by synthetic methods. Both, the racemic and the chiral succinimides were tested simultaneously by the microbroth dilution method of CLSI against a panel of human opportunistic pathogenic fungi of clinical importance. Chiral succinimides showed higher antifungal activity than the corresponding racemic ones and the differences in activity were established by statistical methods. The bottlenecks for developing chiral drugs are how to obtain them through a low-cost procedure and with high enantiomeric excess. Results presented here accomplish both these objectives, opening an avenue for the development of asymmetric succinimides as new antifungal drugs for pharmaceutical use.

  利用烟曲霉菌对马来酰亚胺进行生物转化，制备了 18 种 (3R) 和 (3R,4R) -N-苯基、N-苯基烷基和 N-芳基丁二酰亚胺，具有很高的对映选择性。这一环保、清洁、经济的过程是通过全细胞真菌生物转化方法实现的。相应的 18 种外消旋琥珀酰亚胺是通过合成方法制备的。外消旋琥珀酰亚胺和手性琥珀酰亚胺同时通过 CLSI 的微流稀释法对一组具有临床重要性的人类机会致病真菌进行了测试。手性琥珀酰亚胺的抗真菌活性高于相应的外消旋琥珀酰亚胺，其活性差异已通过统计方法确定。开发手性药物的瓶颈在于如何通过低成本程序获得高对映体过量的药物。本文介绍的结果实现了这两个目标，为开发不对称琥珀酰亚胺作为新的抗真菌药物开辟了一条途径。