Epibestatin | 61046-23-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: Epibestatin
• 英文别名: ubenimex；(2S)-2-[[(2R,3R)-3-azaniumyl-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoate
• CAS: 61046-23-9
• 化学式: C₁₆H₂₄N₂O₄
• 分子量: 308.378
• InChiKey: VGGGPCQERPFHOB-HZSPNIEDSA-N

物化性质

• 沸点：
  604.7±55.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-cbz-(2r,3r)-3-氨基-2-羟基-4-苯基丁酸 在 钯 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 Epibestatin
  参考文献：
  名称：

  Synthesis and structure-activity relations of bestatin analogs, inhibitors of aminopeptidase B

  摘要：

  Stereoisomers and analogues of bestatin, [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-leucine, were synthesized and tested for aminopeptidase B and leucine aminopeptidase inhibiting activity. Among the eight stereoisomers, the 2S stereoisomers exhibited strong activity. In a series of compounds in which the L-leucine residue of bestatin was substituted with other amino acids, only the one containing isoleucine showed more activity than bestatin. Norleucine, norvaline, methionine, valine, serine, glutamine, phenylalanine, glutamic acid, proline, and lysine analogues gave, in that order, decreasing activity. Alkyl and phenyl sub stitution for the benzyl group of bestatin decreased the activity markedly. p-Methyl-, p-chloro-, and p-nitrobestatins showed greater activity than bestatin.

  DOI：

  10.1021/jm00214a010

文献信息

• 一种乌苯美司的新型合成工艺
  申请人：成都傲飞生物化学品有限责任公司

  公开号：CN104447394B

  公开（公告）日：2017-01-18

  本发明公开一种乌苯美司的新型合成工艺，以（2S，3R）‑3‑氨基‑2‑羟基‑4‑苯基丁酸为原料，与二碳酸二叔丁酯反应，且二碳酸二叔丁酯采用分批逐次的加入方式，制备获得中间体I，中间体I与L‑亮氨酸叔丁酯盐酸盐反应制备获得中间体II，其中L‑亮氨酸叔丁酯盐酸盐作为优选，有利于提高中间体II的收率和纯度，中间体II在酸碱体系下分别脱去保护基团叔丁氧羰酰基和叔丁酯，此操作只需通过酸碱体系调节酸碱值就能有效将保护基团高效脱去，提高乌苯美司成品的收率和纯度。
• Plasminogen Activator Inhibitor-1 Inhibitors and Methods of Use Thereof to Modulate Lipid Metabolism
  申请人：Lawrence Daniel A.

  公开号：US20100137194A1

  公开（公告）日：2010-06-03

  The invention relates to plasminogen activator-1 (PAI-1) inhibitor compounds and uses thereof in the treatment of any disease or condition associated with elevated PAI-1. The invention includes, but is not limited to, the use of such compounds to modulate lipid metabolism and treat conditions associated with elevated PAI-1, cholesterol, or lipid levels.

  本发明涉及纤溶酶原激活剂-1（PAI-1）抑制剂化合物及其在治疗任何与升高的PAI-1相关的疾病或病状中的应用。本发明包括但不限于使用这些化合物来调节脂质代谢并治疗与升高的PAI-1、胆固醇或脂质水平相关的病症。
• PLASMINOGEN ACTIVATOR INHIBITOR-1 INHIBITORS AND METHODS OF USE THEREOF TO MODULATE LIPID METABOLISM
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20160009748A1

  公开（公告）日：2016-01-14

  The invention relates to plasminogen activator-1 (PAI-1) inhibitor compounds and uses thereof in the treatment of any disease or condition associated with elevated PAI-1. The invention includes, but is not limited to, the use of such compounds to modulate lipid metabolism and treat conditions associated with elevated PAI-1, cholesterol, or lipid levels.

  本发明涉及纤溶酶原激活物-1（PAI-1）抑制剂化合物及其在治疗与升高的PAI-1相关的任何疾病或病况中的用途。本发明包括但不限于使用这样的化合物来调节脂质代谢并治疗与升高的PAI-1、胆固醇或脂质水平相关的病症。
• Treatment of aging-associated disease with modulators of leukotriene A4 hydrolase
  申请人：Alkahest, Inc.

  公开号：US11344542B2

  公开（公告）日：2022-05-31

  Methods and compositions for treating and/or preventing aging-related conditions are described. The compositions used in the methods include inhibitors or antagonists of leukotriene A4 hydrolase (“LTA4H”) with efficacy in treating and/or preventing aging-related conditions such as neurocognitive disorders.

  本文描述了治疗和/或预防衰老相关疾病的方法和组合物。这些方法中使用的组合物包括白三烯 A4水解酶（"LTA4H"）的抑制剂或拮抗剂，具有治疗和/或预防神经认知障碍等衰老相关疾病的功效。
• STABILIZING SOLUTIONS FOR TROPONIN
  申请人：DADE BEHRING INC.

  公开号：EP0759074B1

  公开（公告）日：1998-07-08