(S)-2-((S)-2-Hydroxy-3-methyl-butyrylamino)-propionic acid | 669074-35-5

• 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)-2-((S)-2-Hydroxy-3-methyl-butyrylamino)-propionic acid
• 英文别名: (2S)-2-[[(2S)-2-hydroxy-3-methylbutanoyl]amino]propanoic acid
• CAS: 669074-35-5
• 化学式: C₈H₁₅NO₄
• 分子量: 189.211
• InChiKey: OXNBDTKGTGHILO-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-((S)-2-Hydroxy-3-methyl-butyrylamino)-propionic acid 、 (2R,4S,5S)-5-Amino-2-ethyl-4-hydroxy-6-phenyl-hexanoic acid [(S)-2-methyl-1-((R)-1-phenyl-ethylcarbamoyl)-propyl]-amide 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,4S,5S)-2-Ethyl-4-hydroxy-5-[(S)-2-((S)-2-hydroxy-3-methyl-butyrylamino)-propionylamino]-6-phenyl-hexanoic acid [(S)-2-methyl-1-((R)-1-phenyl-ethylcarbamoyl)-propyl]-amide
  参考文献：
  名称：

  P3 cap modified Phe*-Ala series BACE inhibitors

  摘要：

  With the aim of reducing molecular weight and adjusting log D value of BACE inhibitors to more favorable range for BBB penetration and better bioavailability, we synthesized and evaluated several series of P3 cap modified BACE inhibitors obtained via replacement of the P3 NHBoc moiety as seen in 3 with other polar functional groups such as amino, hydroxyl and fluorine. Several promising inhibitors emerging from this P3 cap SAR study (e.g., 15 and 19) demonstrated good enzyme inhibitory potencies (BACE-1 IC50 < 50 nM) and whole cell activities (IC50 similar to 1 muM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.085
• 作为产物：
  描述：

  (S)-2-((S)-2-Hydroxy-3-methyl-butyrylamino)-propionic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (S)-2-((S)-2-Hydroxy-3-methyl-butyrylamino)-propionic acid
  参考文献：
  名称：

  P3 cap modified Phe*-Ala series BACE inhibitors

  摘要：

  With the aim of reducing molecular weight and adjusting log D value of BACE inhibitors to more favorable range for BBB penetration and better bioavailability, we synthesized and evaluated several series of P3 cap modified BACE inhibitors obtained via replacement of the P3 NHBoc moiety as seen in 3 with other polar functional groups such as amino, hydroxyl and fluorine. Several promising inhibitors emerging from this P3 cap SAR study (e.g., 15 and 19) demonstrated good enzyme inhibitory potencies (BACE-1 IC50 < 50 nM) and whole cell activities (IC50 similar to 1 muM). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.085

文献信息

• [EN] MACROCYCLIC COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS MACROCYCLIQUES ET LEURS UTILISATIONS
  申请人：[en]CYPRALIS LIMITED

  公开号：WO2023223057A1

  公开（公告）日：2023-11-23

  The invention relates to selected macrocyclic compounds, and their use in the treatment or prevention of diseases and disorders. In particular, though not exclusively, the invention relates to the use of selected macrocyclic compounds in the treatment or prevention of diseases that are caused by (1) cell death due to various causes and (2) inflammation. Such diseases can affect all parts of the body, including the central and peripheral nervous systems, all organs and tissues, the muscles, the vasculature and the bones.
• P3 cap modified Phe*-Ala series BACE inhibitors
  作者：Shu-Hui Chen、Jason Lamar、Deqi Guo、Todd Kohn、Hsiu-Chiung Yang、James McGee、David Timm、Jon Erickson、Yvonne Yip、Patrick May、James McCarthy

  DOI：10.1016/j.bmcl.2003.09.085

  日期：2004.1

  With the aim of reducing molecular weight and adjusting log D value of BACE inhibitors to more favorable range for BBB penetration and better bioavailability, we synthesized and evaluated several series of P3 cap modified BACE inhibitors obtained via replacement of the P3 NHBoc moiety as seen in 3 with other polar functional groups such as amino, hydroxyl and fluorine. Several promising inhibitors emerging from this P3 cap SAR study (e.g., 15 and 19) demonstrated good enzyme inhibitory potencies (BACE-1 IC50 < 50 nM) and whole cell activities (IC50 similar to 1 muM). (C) 2003 Elsevier Ltd. All rights reserved.