(S)-7-[4-(2-thienyl)butylcarboxamido]isochroman-3-carboxylic acid | 1170960-59-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-7-[4-(2-thienyl)butylcarboxamido]isochroman-3-carboxylic acid
• 英文别名: (3S)-7-[4-(2-Thienyl)butylcarboxamido]-isochroman-3-carboxylic acid；(3S)-7-(5-thiophen-2-ylpentanoylamino)-3,4-dihydro-1H-isochromene-3-carboxylic acid
• CAS: 1170960-59-4
• 化学式: C₁₉H₂₁NO₄S
• 分子量: 359.446
• InChiKey: NFXYGJNCWVDKLI-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 水 、 potassium carbonate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 (S)-7-[4-(2-thienyl)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