(S)-3-amino-2-methylpropionic acid methyl ester hydrochloride | 168828-17-9

• 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-amino-2-methylpropionic acid methyl ester hydrochloride
• 英文别名: (S)-β-Aib-OCH3；(S)-Methyl 3-amino-2-methylpropanoate hydrochloride；methyl (2S)-3-amino-2-methylpropanoate;hydrochloride
• CAS: 168828-17-9
• 化学式: C₅H₁₁NO₂*ClH
• 分子量: 153.609
• InChiKey: RVPWGKBKRYTOHJ-WCCKRBBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.18
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-1-苯乙基异氰酸酯 、 (S)-3-amino-2-methylpropionic acid methyl ester hydrochloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  3-甲基氮杂环丁烷-2-酮及其前体：光学分辨率和绝对构型

  摘要：

  3-甲基氮杂环丁烷-2-酮-（3 R）-（+）-和（3S）-（-）-1的对映体以及3-氨基-2-甲基丙酸-（2R）-（-）-和从（αS）-N-α-甲基苄基-3-氨基-2-甲基丙酸甲酯3A，B的相应非对映异构体获得（2S）-（+）-2 ，该化合物已通过将其盐4A，B与p重结晶而分离-甲苯磺酸。氮杂环丁烷酮（+）-和（-）- 1及其非对映异构体前体的绝对构型，即氨基酯3A，B，（αS）-N - α-甲基苄基-3-氨基-2-甲基丙酸5A，B和（αS）-通过将（+）- 1转化为氨基酸（2R）-（-）-2和将氨基酸（2S）-（+）-转化为N - α-甲基苄基-3-甲基氮杂环丁烷-2-酮6A，B。 2至（-）- 1。

  DOI：

  10.1016/0957-4166(96)00065-1
• 作为产物：
  描述：

  (S)-3-叠氮基-2-甲基丙酸甲酯 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以2.0 g的产率得到(S)-3-amino-2-methylpropionic acid methyl ester hydrochloride
  参考文献：
  名称：

  Structural Modification of the P2‘ Position of 2,7-Dialkyl-Substituted 5(S)-Amino-4(S)-hydroxy-8-phenyl-octanecarboxamides:  The Discovery of Aliskiren, a Potent Nonpeptide Human Renin Inhibitor Active after Once Daily Dosing in Marmosets

  摘要：

  Due to its function in the rate limiting initial step of the renin-angiotensin system, renin is a particularly promising target for drugs designed to control hypertension, a growing risk to health worldwide. Despite vast efforts over more than two decades, no orally efficacious renin inhibitor had reached the market. As a result of a structure-based topological design approach, we have identified a novel class of small-molecule inhibitors with good oral blood-pressure lowering effects in primates. Further lead optimization aimed for improvement of in vivo potency and duration of action, mainly by P2' modifications at the hydroxyethylene transition-state isostere. These efforts resulted in the discovery of aliskiren (46, CGP060536B, SPP100), a highly potent, selective inhibitor of renin, demonstrating excellent efficacy in sodium-depleted marmosets after oral administration, with sustained duration of action in reducing dose-dependently mean arterial blood pressure. Aliskiren has recently received regulatory approval by the U.S. Food and Drug Administration for the treatment of hypertension.

  DOI：

  10.1021/jm070316i

文献信息

• Methods of treating alzheimer's disease using aryl alkanoic acid amides
  申请人：John Varghese

  公开号：US20060154926A1

  公开（公告）日：2006-07-13

  Disclosed are methods for treating Alzheimer's disease, and other diseases, and/or inhibiting beta-secretase enzyme, and/or inhibiting deposition of A beta peptide in a mammal, by use of compounds of formula (1) wherein the variables R 1 -R 8 and X are defined herein.

  本发明涉及使用式（1）中所述的化合物治疗阿尔茨海默病和其他疾病，抑制β-分泌酶酶活性和/或抑制Aβ肽在哺乳动物体内的沉积的方法，其中变量R1-R8和X在此定义。
• Delta-Amino-gamma-hydroxy-omega-aryl-alkansäureamide mit Enzym-, insbesondere Renin-hemmenden Eigenschaften
  申请人：Novartis AG

  公开号：EP0678503B1

  公开（公告）日：1999-09-01
• Bioconjugates of 1′‐Aminoferrocene‐1‐carboxylic Acid with ( <i>S</i> )‐3‐Amino‐2‐methylpropanoic Acid and <scp>L</scp> ‐Alanine
  作者：Mojca Čakić Semenčić、Katja Heinze、Christoph Förster、Vladimir Rapić

  DOI：10.1002/ejic.200901146

  日期：2010.3

  AbstractFormal CH2 insertion in bioconjugates composed of 1′‐aminoferrocene‐1‐carboxylic acid (Fca) and alanine Boc‐Ala‐Fca‐Ala‐OCH3 gives Fca bioconjugates with the β‐amino acid (S)‐3‐amino‐2‐methylpropanoic acid (Aib). The novel homologous conjugates of ferrocene were fully characterized by spectroscopic and analytical methods. NMR, CD and IR spectroscopy in concert with DFT calculations suggest that the formal “L‐Ala–to–(S)‐β‐Aib mutations” can exert ferrocene helix inversion due to the different stereogenic carbon atoms of L‐Ala and (S)‐β‐Aib. Furthermore, the mutation (de‐)stabilizes the conserved secondary structure with two intramolecular hydrogen bonds, depending on the “mutation site”. The systematic work presented provides a firm basis for understanding the factors that determine folding in bioconjugates of ferrocene and β‐amino acids and will guide the rational design of metallocene peptidomimetics incorporating β‐amino acids.
• US5559111A
  申请人：——

  公开号：US5559111A

  公开（公告）日：1996-09-24
• US5627182A
  申请人：——

  公开号：US5627182A

  公开（公告）日：1997-05-06