2-(2-(((S)-1-(3-(4-hydroxybenzyl)-5-((S)-2-amino-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)methyl)phenyl)acetic acid | 1062260-88-1

• 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: 2-(2-(((S)-1-(3-(4-hydroxybenzyl)-5-((S)-2-amino-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)methyl)phenyl)acetic acid
• 英文别名: 2-[2-[[[(2S)-1-[3-[[(2S)-2-amino-3-methylbutanoyl]amino]-5-[(4-hydroxyphenyl)methyl]benzoyl]pyrrolidine-2-carbonyl]amino]methyl]phenyl]acetic acid
• CAS: 1062260-88-1
• 化学式: C₃₃H₃₈N₄O₆
• 分子量: 586.688
• InChiKey: LNXGXUXEWRYUPG-JDXGNMNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  162
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-(9H-fluoren-ylmethoxycarbonylamino)-5-(4-hydroxybenzyl)benzoic acid 、 [2-(叠氮基甲基)苯基]乙酸 、 Fmoc-L-缬氨酸 、 Fmoc-L-脯氨酸 以5.9 mg的产率得到2-(2-(((S)-1-(3-(4-hydroxybenzyl)-5-((S)-2-amino-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)methyl)phenyl)acetic acid
  参考文献：
  名称：

  Ligands to the (IRAP)/AT4 receptor encompassing a 4-hydroxydiphenylmethane scaffold replacing Tyr2

  摘要：

  Analogues of the hexapeptide angiotensin IV (Ang IV, Val(1)-Tyr(2)-Ile(3)-His(4)-Pro(5)-Phe(6)) encompassing a 4-hydroxydiphenylmethane scaffold replacing Tyr(2) and a phenylacetic or benzoic acid moiety replacing His4-Pro5-Phe6 have been synthesized and evaluated in biological assays. The analogues inhibited the proteolytic activity of cystinyl aminopeptidase ( CAP), frequently referred to as the insulin-regulated aminopeptidase ( IRAP), and were found less efficient as inhibitors of aminopeptidase N (AP-N). The best Ang IV mimetics in the series were approximately 20 times less potent than Ang IV as IRAP inhibitors. Furthermore, it was found that the ligands at best exhibited a 140 times lower binding affinity to the membrane-bound IRAP/AT4 receptor than Ang IV. Although the best compounds still exert lower activities than Ang IV, it is notable that these compounds comprise only two amino acid residues and are considerably less peptidic in character than the majority of the Ang IV analogues previously reported as IRAP inhibitors in the literature. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.046