(RS)-3-carboxy-4-chlorophenylalanine | 13406-46-7

• 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: (RS)-3-carboxy-4-chlorophenylalanine
• 英文别名: (3-Carboxy-4-chlorphenyl)-alanin；DL-alpha-Amino-3-carboxy-4-chlorohydrocinnamic acid；5-(2-amino-2-carboxyethyl)-2-chlorobenzoic acid
• CAS: 13406-46-7
• 化学式: C₁₀H₁₀ClNO₄
• 分子量: 243.647
• InChiKey: CZQFEVBWZSZLCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  459.5±45.0 °C(Predicted)
• 密度：
  1.504±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯-5-甲基苯甲酸 在 盐酸 作用下， 生成 (RS)-3-carboxy-4-chlorophenylalanine
  参考文献：
  名称：

  非天然氨基酸。二。DL -3-羧基-4-甲氧基苯基丙氨酸的同类物。

  摘要：

  DOI：

  10.1021/jm00315a040

文献信息

• Structure-activity relationships of new agonists and antagonists of different metabotropic glutamate receptor subtypes
  作者：N. Sekiyama、Y. Hayashi、S. Nakanishi、D.E. Jane、H-W. Tse、E.F. Birse、J.C. Watkins

  DOI：10.1111/j.1476-5381.1996.tb15312.x

  日期：1996.4

  1 We investigated the agonist and atagonist activities of 22 new phenylglycine and phenylalamine derivatives for metabotropic glutamate receptors (mGluRs) by examining their effects on the signal transduction of mGluR(1), mGluR(2) and mGluR(6) subtypes expressed in Chinese hamster ovary cells. This analysis revealed several structural characteristics that govern receptor subtype specificity of the agonist and antagonist activities of phenylglycine derivatives.2 Hydroxyphenylglycine derivatives possessed either an agonist activity on mGluR(1) mGluR(6) or an antagonist activity on mGluR(1).3 Carboxyphenylglycine derivatives showed an agonist activity on mGluR(2) but an antagonist activity on mGluR(1).4 alpha-Methylation or alpha-ethylation of the carboxyphenylglycine derivatives converts the agonist property For mGluR(2) to an antagonist property, thus producing antagonists at both mGluR(1) and mGluR(2).5 Structurally-corresponding phenylalanine derivatives showed little or no agonist or antagonist activity on any subtypes of the receptors.6 This investigation demonstrates that the nature and positions of side chains and ring substituents incorporated into the phenylglycine structure are critical in determining the agonist and antagonist activities of members of this group of compounds on different subtypes of the mGluR family.7 We also tested two alpha-methyl derivatives of mGluR agonists. (2S, 1'S, 2'S)-2-(2-Carboxycyciopropyl)glycine (L-CCG-I) is a potent agonist for mGluR(2) but alpha-methylation of this compound changes its activity to that of an mGluR(2)-selective antagonist. In contrast, alpha-methylation of L-2-amino-4-phosphonobutyrate (L-AP4) results in retention of an agonist activity on mCluR(6). Thus, alpha-methylation produces different effects, depending on the chemical structures of lead compounds and/or on the subtype of mGluR tested.
• Unnatural Amino Acids. II. Congeners of <scp>DL</scp>-3-Carboxy-4-methoxyphenylalanine
  作者：Frederick. Leonard、Abraham. Wajngurt、Walter. Tschannen、M. Klein

  DOI：10.1021/jm00315a040

  日期：1967.5