(S)-7-[4-(1,2-dithiolan-3-yl)butylcarboxamido]isochroman-3-carboxylic acid | 938042-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: (S)-7-[4-(1,2-dithiolan-3-yl)butylcarboxamido]isochroman-3-carboxylic acid
• 英文别名: (3S)-7-[4-(1,2-Dithiolan-3-yl)butylcarboxamido]-isochroman-3-carboxylic acid；(3S)-7-[5-(dithiolan-3-yl)pentanoylamino]-3,4-dihydro-1H-isochromene-3-carboxylic acid
• CAS: 938042-63-8
• 化学式: C₁₈H₂₃NO₄S₂
• 分子量: 381.517
• InChiKey: KRQHPRIBLJFGIT-LYKKTTPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl (3S)-7-(5-(1,2-dithiolan-3-yl)pentanamido)isochromane-3-carboxylate 在 水 、 potassium carbonate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 (S)-7-[4-(1,2-dithiolan-3-yl)butylcarboxamido]isochroman-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of some novel isochroman carboxylic acid derivatives as potential anti-diabetic agents

  摘要：

  A series of novel isochroman mono-carboxylic acid derivatives were synthesized, characterized and evaluated for their ability to inhibit protein tyrosine phosphatase 1B (PTP1B) in vitro in order to use them as potential anti-diabetic agents. Analysis of structure-activity relationships led to the identification of potent compound 4n which inhibited PTP1B with IC50 value of 51.63 +/- 0.91 nM. In general, high potency was associated with a dithiolane ring with a spacer of five carbons to the isochroman ring. Compound 4n has been selected for in vivo evaluation as drug candidate for anti-diabetic activity. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.009

文献信息

• Synthesis and evaluation of some novel isochroman carboxylic acid derivatives as potential anti-diabetic agents
  作者：N. Lakshminarayana、Y. Rajendra Prasad、Laxmikant Gharat、Abraham Thomas、P. Ravikumar、Shridhar Narayanan、C.V. Srinivasan、Balasubramanian Gopalan

  DOI：10.1016/j.ejmech.2009.03.009

  日期：2009.8

  A series of novel isochroman mono-carboxylic acid derivatives were synthesized, characterized and evaluated for their ability to inhibit protein tyrosine phosphatase 1B (PTP1B) in vitro in order to use them as potential anti-diabetic agents. Analysis of structure-activity relationships led to the identification of potent compound 4n which inhibited PTP1B with IC50 value of 51.63 +/- 0.91 nM. In general, high potency was associated with a dithiolane ring with a spacer of five carbons to the isochroman ring. Compound 4n has been selected for in vivo evaluation as drug candidate for anti-diabetic activity. (C) 2009 Elsevier Masson SAS. All rights reserved.