(R)-2-(4-amino-4-carboxybutyl)benzoic acid | 1587692-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-(4-amino-4-carboxybutyl)benzoic acid
• 英文别名: 2-[(4R)-4-amino-4-carboxybutyl]benzoic acid
• CAS: 1587692-45-2
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: CXFUXDHRXUFBFW-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (R)-甲基-2-Boc-氨基-4-戊烯酸 在 5%-palladium/activated carbon 、 水 、 氢气 、 palladium diacetate 、 N,N-二异丙基乙胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 7.0h， 生成 (R)-2-(4-amino-4-carboxybutyl)benzoic acid
  参考文献：
  名称：

  Efficient synthesis of novel glutamate homologues and investigation of their affinity and selectivity profile at ionotropic glutamate receptors

  摘要：

  A convenient synthesis of four new enantiomerically pure acidic amino acids is reported and their affinity at ionotropic glutamate receptors was determined. The new compounds are higher homologues of glutamic acid in which the molecular complexity has been increased by introducing an aromatic/heteroaromatic ring, that is a phenyl or a thiophene ring, that could give additional electronic interactions with the receptors. The results of the present investigation indicate that the insertion of an aromatic/heteroaromatic ring into the amino acid skeleton of glutamate higher homologues is well tolerated and this modification could be exploited to generate a new class of NMDA antagonists. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.058

文献信息

• Efficient synthesis of novel glutamate homologues and investigation of their affinity and selectivity profile at ionotropic glutamate receptors
  作者：Andrea Pinto、Lucia Tamborini、Federica Mastronardi、Roberta Ettari、Diego Romano、Birgitte Nielsen、Carlo De Micheli、Paola Conti

  DOI：10.1016/j.bmcl.2014.02.058

  日期：2014.4

  A convenient synthesis of four new enantiomerically pure acidic amino acids is reported and their affinity at ionotropic glutamate receptors was determined. The new compounds are higher homologues of glutamic acid in which the molecular complexity has been increased by introducing an aromatic/heteroaromatic ring, that is a phenyl or a thiophene ring, that could give additional electronic interactions with the receptors. The results of the present investigation indicate that the insertion of an aromatic/heteroaromatic ring into the amino acid skeleton of glutamate higher homologues is well tolerated and this modification could be exploited to generate a new class of NMDA antagonists. (C) 2014 Elsevier Ltd. All rights reserved.