(S)-3-hydroxy-2-(3-phenylpropionylamino)propionic acid | 130766-04-0

• 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: (S)-3-hydroxy-2-(3-phenylpropionylamino)propionic acid
• 英文别名: N-(3-phenylpropanoyl)-L-Ser-OH；(2S)-3-hydroxy-2-(3-phenylpropanoylamino)propanoic acid
• CAS: 130766-04-0
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: ZKAJWHICESOZDJ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 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：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-丝氨酸 、 3-苯丙酰氯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以40%的产率得到(S)-3-hydroxy-2-(3-phenylpropionylamino)propionic acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of N-(2-Oxo-3-oxetanyl)amides as N-Acylethanolamine-hydrolyzing Acid Amidase Inhibitors

  摘要：

  The fatty acid ethanolamides (FAEs) are a family of bioactive lipid mediators that include the endogenous agonist of peroxisome proliferator-activated receptor-alpha, palmitoylethanolamide (PEA). FAEs are hydrolyzed intracellularly by either fatty acid amide hydrolase or N-acylethanolamine-hydrolyzing acid amidase (NAAA). Selective inhibition of NAAA by (S)-N-(2-oxo-3-oxetanyl)-3-phenylpropionamide [(S)-OOPP, 7a] prevents PEA degradation in mouse leukocytes and attenuates responses to proinflammatory stimuli. Starting from the structure of 7a, a series of beta-lactones was prepared and tested on recombinant rat NAAA to explore structure-activity relationships (SARs) for this class of inhibitors and improve their in vitro potency. Following the hypothesis that these compounds inhibit NAAA by acylation of the catalytic cysteine, we identified several requirements for recognition at the active site and obtained new potent inhibitors. In particular, (S)-N-(2-oxo-3-oxetanyl)biphenyl-4-carboxamide (7h) was more potent than 7a at inhibiting recombinant rat NAAA activity (7a, IC(50) = 420 nM; 7h, IC(50) = 115 nM) in vitro and at reducing carrageenan-induced leukocyte infiltration in vivo.

  DOI：

  10.1021/jm100582w

文献信息

• Ecological Base-Conditioned Preparation of Dipeptides Using Unprotected α-Amino Acids Containing Hydrophilic Side Chains
  作者：Tetsuya Ezawa、Seunghee Jung、Yuya Kawashima、Takuya Noguchi、Nobuyuki Imai

  DOI：10.1246/bcsj.20170035

  日期：2017.6.15

  The coupling reactions of 3-phenylpropanoic acid and N-carboxybenzyl α-amino acids with unprotected α-amino acids containing hydrophilic side chains such as aliphatic alcohol, aromatic alcohol, thiol, carboxylic acid, and amide afforded the corresponding amides in 66–96% yield without racemization via the corresponding mixed carbonic carboxylic anhydrides under basic conditions through an ecological

  3-苯基丙酸和N-羧基苄基α-氨基酸与含有亲水侧链的未保护α-氨基酸如脂肪醇、芳香醇、硫醇、羧酸和酰胺的偶联反应得到66-96%的相应酰胺通过生态绿色合成方法，在碱性条件下通过相应的混合碳酸酐不发生外消旋化的收率。
• Convenient Peptide Synthesis Using Unprotected α-Amino Acids Containing Another Hydrophilic Moiety under Basic Conditions
  作者：Takuya Noguchi、Seunghee Jung、Nobuyuki Imai

  DOI：10.1246/cl.2012.577

  日期：2012.6.5

  Carboxylic acids 1 and 7 reacted effectively with unprotected α-amino acids 2 containing another hydrophilic moiety under basic conditions via activation by ethyl chloroformate and triethylamine to afford the corresponding amides in 74–99% yields.

  在碱性条件下，羧酸 1 和 7 通过氯甲酸乙酯和三乙胺的活化作用，与含有另一个亲水分子的未受保护的 α- 氨基酸 2 发生有效反应，生成相应的酰胺，产率为 74-99%。
• Compositions and methods of inhibiting N-acylethanolamine-hydrolyzing acid amidase
  申请人：The Regents of the University of California

  公开号：US10363237B2

  公开（公告）日：2019-07-30

  Compounds and pharmaceutical compositions are contemplated that inhibit N-acyl-ethanolamine-hydrolyzing acid amidase (NAAA) to so increase the concentration of the substrate of NAAA, palmitoylethanolamide (PEA). NAAA inhibition is contemplated to be effective to alleviate conditions associated with a reduced concentration of PEA. Among other uses, various NAAA inhibitors are especially contemplated as therapeutic agents in the treatment of inflammatory diseases.

  考虑使用抑制 N-酰基乙醇胺水解酸酰胺酶（NAAA）的化合物和药物组合物，以提高 NAAA 底物棕榈酰乙醇酰胺（PEA）的浓度。NAAA 抑制可有效缓解与 PEA 浓度降低有关的状况。除其他用途外，特别考虑将各种 NAAA 抑制剂作为治疗炎症性疾病的治疗剂。
• ALPHA-AMIDES OF L-AMINO ACIDS AS FRAGRANCE PRECURSORS
  申请人：THE GILLETTE COMPANY

  公开号：EP1047391A1

  公开（公告）日：2000-11-02
• EP1047391A4
  申请人：——

  公开号：EP1047391A4

  公开（公告）日：2005-01-19