(S)-6-aminoisochroman-3-carboxylic acid methyl ester | 938042-52-5

• 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)-6-aminoisochroman-3-carboxylic acid methyl ester
• 英文别名: methyl (3S)-6-amino-3,4-dihydro-1H-isochromene-3-carboxylate
• CAS: 938042-52-5
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: MMAUREFYWOLOCH-JTQLQIEISA-N

物化性质

• 熔点：
  121 °C
• 沸点：
  361.3±42.0 °C(predicted)
• 密度：
  1.239±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-6-aminoisochroman-3-carboxylic acid methyl ester 、 R-(+)-硫辛酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  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
• 作为产物：
  描述：

  (S)-isochroman-3-carboxylic acid methyl ester 在 硝酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， -40.0 ℃ 、413.69 kPa 条件下， 反应 3.67h， 生成 (S)-7-aminoisochroman-3-carboxylic acid methyl ester 、 (S)-6-aminoisochroman-3-carboxylic acid methyl ester
  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.