(2S)-2-[(trans-4-isopropyl-cyclohexanecarbonyl)amino]-3-(4-hydroxyphenyl)propionic acid methyl ester | 727985-87-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-[(trans-4-isopropyl-cyclohexanecarbonyl)amino]-3-(4-hydroxyphenyl)propionic acid methyl ester
• 英文别名: (2S)-2-[N-(trans-4-isopropylcyclohexylcarbonyl)amino]-3-(4-hydroxyphenyl)-propionic acid methyl ester
• CAS: 727985-87-7
• 化学式: C₂₀H₂₉NO₄
• 分子量: 347.455
• InChiKey: SPVCLBZJUUQTTK-BQFCYCMXSA-N

物化性质

• 熔点：
  123-126 °C
• 沸点：
  537.7±38.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(trans-4-isopropyl-cyclohexanecarbonyl)amino]-3-(4-hydroxyphenyl)propionic acid methyl ester 在 lithium hydroxide 、 水 作用下， 以81.1%的产率得到(2S)-2-[N-(trans-4-isopropylcyclohexylcarbonyl)amino]-3-(4-hydroxyphenyl)-propionic acid
  参考文献：
  名称：

  Insulin-releasing activity of a series of phenylalanine derivatives

  摘要：

  A series of phenylalanine derivatives were synthesized and their biological activities were evaluated. Compounds (S)-3 and (R)-3 exhibited more potent insulin-releasing activity than that of nateglinide, compound (S)-3 also showed insulin-sensitizing activity in vitro. Both compounds were tested for hypoglycemia effect in vivo. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.11.018
• 作为产物：
  描述：

  L-酪氨酸甲酯 、 Trans-4-Isopropylcyclohexane Carboxylic Acid 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 27.0h， 以37.8%的产率得到(2S)-2-[(trans-4-isopropyl-cyclohexanecarbonyl)amino]-3-(4-hydroxyphenyl)propionic acid methyl ester
  参考文献：
  名称：

  Insulin-releasing activity of a series of phenylalanine derivatives

  摘要：

  A series of phenylalanine derivatives were synthesized and their biological activities were evaluated. Compounds (S)-3 and (R)-3 exhibited more potent insulin-releasing activity than that of nateglinide, compound (S)-3 also showed insulin-sensitizing activity in vitro. Both compounds were tested for hypoglycemia effect in vivo. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.11.018

文献信息

• Alanines compounds, method of preparing them and their use
  申请人：Yang Yushe

  公开号：US20060154970A1

  公开（公告）日：2006-07-13

  The present invention provides alanines compounds of formula (I) or their salts: In the formula (I), the configuration of α-Carbon atom of alanine is R or S; R 1 is hydrogen, unsubstituted or substituted C 1-6 alkyl, unsubstituted or substituted aryl or aromatic heterocyclic group; R 2 is hydrogen or unsubstituted or substituted C 1-6 alkyl. The present invention also provides two methods of preparing these compounds or their salts, and their use in preparing anti II type diabetic medicine.

  本发明提供了公式(I)的丙氨酸化合物或其盐： 在公式(I)中，丙氨酸的α-碳原子的构型为R或S；R1是氢，未取代或取代的C1-6烷基，未取代或取代的芳基或芳香杂环基；R2是氢或未取代或取代的C1-6烷基。本发明还提供了制备这些化合物或其盐的两种方法，并将其用于制备抗II型糖尿病药物。
• ALANINES COMPOUNDS, METHOD OF PREPARING THEM AND THEIR USE
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：EP1591440A1

  公开（公告）日：2005-11-02

  The present invention provides alanine compounds of formula (I) or their salts: In the formula (I), the configuration of α ― Carbon atom of alanine is R or S; R1 is hydrogen, unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted aromatic ring or aromatic heterocyclic ring; R2 is hydrogen or unsubstituted or substituted C1-6 alkyl. The present invention also provides two methods of preparing these compounds or their salts, and their use in preparing anti II type diabetic medicine.

  本发明提供了式 (I) 的丙氨酸化合物或其盐类： 式（I）中，丙氨酸的α-碳原子的构型为R或S；R1为氢、未取代或取代的C1-6烷基、未取代或取代的芳香环或芳香杂环；R2为氢或未取代或取代的C1-6烷基。本发明还提供了制备这些化合物或其盐的两种方法，以及它们在制备抗 II 型糖尿病药物中的用途。
• EP1591440
  申请人：——

  公开号：——

  公开（公告）日：——
• Insulin-releasing activity of a series of phenylalanine derivatives
  作者：Lei Tang、Juanhong Yu、Haoshu Wu、Houxing Fan、Yushe Yang、Ruyun Ji

  DOI：10.1016/j.ejmech.2007.11.018

  日期：2008.9

  A series of phenylalanine derivatives were synthesized and their biological activities were evaluated. Compounds (S)-3 and (R)-3 exhibited more potent insulin-releasing activity than that of nateglinide, compound (S)-3 also showed insulin-sensitizing activity in vitro. Both compounds were tested for hypoglycemia effect in vivo. (C) 2007 Elsevier Masson SAS. All rights reserved.