5-[(2-Phenylethyl)Sulfanyl]Phthalimide | 1403670-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5-[(2-Phenylethyl)Sulfanyl]Phthalimide
• 英文别名: 5-(2-phenylethylsulfanyl)isoindole-1,3-dione
• CAS: 1403670-98-3
• 化学式: C₁₆H₁₃NO₂S
• 分子量: 283.351
• InChiKey: LYRVBHRAOSHOJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯乙硫醇 、 4-硝基邻苯二甲酰亚胺 在 potassium carbonate 、 盐酸 作用下， 以 丙酮 、 水 为溶剂， 反应 24.0h， 以75%的产率得到5-[(2-Phenylethyl)Sulfanyl]Phthalimide
  参考文献：
  名称：

  Novel sulfanylphthalimide analogues as highly potent inhibitors of monoamine oxidase B

  摘要：

  Monoamine oxidase (MAO) plays an essential role in the catabolism of neurotransmitter amines. The two isoforms of this enzyme, MAO-A and -B, are considered to be drug targets for the therapy of depression and neurodegenerative diseases, respectively. Based on a recent report that the phthalimide moiety may be a useful scaffold for the design of potent MAO-B inhibitors, the present study examines a series of 5-sulfanylphthalimide analogues as potential inhibitors of both human MAO isoforms. The results document that 5-sulfanylphthalimides are highly potent and selective MAO-B inhibitors with all of the examined compounds possessing IC50 values in the nanomolar range. The most potent inhibitor, 5-(benzylsulfanyl)phthalimide, exhibits an IC50 value of 0.0045 mu M for the inhibition of MAO-B with a 427-fold selectivity for MAO-B compared to MAO-A. We conclude that 5-sulfanylphthalimides represent an interesting class of MAO-B inhibitors and may serve as lead compounds for the design of antiparkinsonian therapy. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.113

文献信息

• Novel sulfanylphthalimide analogues as highly potent inhibitors of monoamine oxidase B
  作者：Mietha M. Van der Walt、Gisella Terre’Blanche、Anél Petzer、Jacobus P. Petzer

  DOI：10.1016/j.bmcl.2012.08.113

  日期：2012.11

  Monoamine oxidase (MAO) plays an essential role in the catabolism of neurotransmitter amines. The two isoforms of this enzyme, MAO-A and -B, are considered to be drug targets for the therapy of depression and neurodegenerative diseases, respectively. Based on a recent report that the phthalimide moiety may be a useful scaffold for the design of potent MAO-B inhibitors, the present study examines a series of 5-sulfanylphthalimide analogues as potential inhibitors of both human MAO isoforms. The results document that 5-sulfanylphthalimides are highly potent and selective MAO-B inhibitors with all of the examined compounds possessing IC50 values in the nanomolar range. The most potent inhibitor, 5-(benzylsulfanyl)phthalimide, exhibits an IC50 value of 0.0045 mu M for the inhibition of MAO-B with a 427-fold selectivity for MAO-B compared to MAO-A. We conclude that 5-sulfanylphthalimides represent an interesting class of MAO-B inhibitors and may serve as lead compounds for the design of antiparkinsonian therapy. (C) 2012 Elsevier Ltd. All rights reserved.