(RS)-α-ethyl-4-carboxyphenylglycine

• 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)-α-ethyl-4-carboxyphenylglycine
• 英文别名: (RS)-alpha-ethyl-4-carboxyphenylglycine；4-(1-Amino-1-carboxypropyl)benzoic acid
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: AIEFWRHRHFRLFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  4-丙酰苯甲酸 、 氰化钾 在 乙酰胺 、 碳酸氢铵 、 盐酸 作用下， 生成 (RS)-α-ethyl-4-carboxyphenylglycine
  参考文献：
  名称：

  Structure-activity relationships of new agonists and antagonists of different metabotropic glutamate receptor subtypes

  摘要：

  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.

  DOI：

  10.1111/j.1476-5381.1996.tb15312.x

文献信息

• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Kõster Hubert

  公开号：US20100248264A1

  公开（公告）日：2010-09-30

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了捕获化合物及其集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。
• US8569481B2
  申请人：——

  公开号：US8569481B2

  公开（公告）日：2013-10-29
• US9034798B2
  申请人：——

  公开号：US9034798B2

  公开（公告）日：2015-05-19
• 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.