3-(N,N-二甲基氨基)-L-丙氨酸 | 10138-99-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 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
• 中文名称: 3-(N,N-二甲基氨基)-L-丙氨酸
• 中文别名: L-Β-(N,N-二甲基氨基)丙氨酸
• 英文名称: (S)-2-amino-3-(dimethylamino)propanoic acid
• 英文别名: 3-(Dimethylamino)-l-alanine；(2S)-2-amino-3-(dimethylamino)propanoic acid
• CAS: 10138-99-5
• 化学式: C₅H₁₂N₂O₂
• 分子量: 132.162
• InChiKey: KEZRWUUMKVVUPT-BYPYZUCNSA-N

物化性质

• 沸点：
  214.3±30.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 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：
  66.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate 、 3-(N,N-二甲基氨基)-L-丙氨酸 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Inhibitors of HIV-1 maturation: Development of structure–activity relationship for C-28 amides based on C-3 benzoic acid-modified triterpenoids

  摘要：

  We have recently reported on the discovery of a C-3 benzoic acid (1) as a suitable replacement for the dimethyl succinate side chain of bevirimat (2), an HIV-1 maturation inhibitor that reached Phase II clinical trials before being discontinued. Recent SAR studies aimed at improving the antiviral properties of 2 have shown that the benzoic acid moiety conferred topographical constraint to the pharmacophore and was associated with a lower shift in potency in the presence of human serum albumin. In this manuscript, we describe efforts to improve the polymorphic coverage of the C-3 benzoic acid chemotype through modifications at the C-28 position of the triterpenoid core. The dimethylaminoethyl amides 17 and 23 delivered improved potency toward bevirimat-resistant viruses while increasing C-24 in rat oral PK studies. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.03.019
• 作为产物：
  描述：

  N-benzyloxycarbonyl-(S)-2-amino-3-(dimethylamino)propanoic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以96.3 %的产率得到3-(N,N-二甲基氨基)-L-丙氨酸
  参考文献：
  名称：

  [EN] COMPOUNDS AS IMMUNOMODULATORS OF PD-L1 INTERACTIONS
  [FR] COMPOSÉS À UTILISER EN TANT QU'IMMUNOMODULATEURS D'INTERACTIONS PD-L1

  摘要：

  PD-L1 inhibitors of various compound formulas, both generically and specifically are disclosed. Methods of making such PD-L1 inhibitor compounds are disclosed, both generically and specifically. Methods of using such PD-L1 inhibitor compounds singly or in combination with additional agents and compositions of such PD-L1 inhibitor compounds for the treatment of cancer and other conditions are disclosed.

  公开号：

  WO2023019430A1

文献信息

• Asymmetric synthesis of β-substituted α-amino acids via a chiral nlii complex of dehydroalanine
  作者：Yuri N. Belokon'、Ashot S. Sagyan、Silva M. Djamgaryan、Vladimir I. Bakhmutov、Vasili M. Belikov

  DOI：10.1016/s0040-4020(01)86056-7

  日期：1988.1
• Inhibitors of HIV-1 maturation: Development of structure–activity relationship for C-28 amides based on C-3 benzoic acid-modified triterpenoids
  作者：Jacob J. Swidorski、Zheng Liu、Sing-Yuen Sit、Jie Chen、Yan Chen、Ny Sin、Brian L. Venables、Dawn D. Parker、Beata Nowicka-Sans、Brian J. Terry、Tricia Protack、Sandhya Rahematpura、Umesh Hanumegowda、Susan Jenkins、Mark Krystal、Ira B. Dicker、Nicholas A. Meanwell、Alicia Regueiro-Ren

  DOI：10.1016/j.bmcl.2016.03.019

  日期：2016.4

  We have recently reported on the discovery of a C-3 benzoic acid (1) as a suitable replacement for the dimethyl succinate side chain of bevirimat (2), an HIV-1 maturation inhibitor that reached Phase II clinical trials before being discontinued. Recent SAR studies aimed at improving the antiviral properties of 2 have shown that the benzoic acid moiety conferred topographical constraint to the pharmacophore and was associated with a lower shift in potency in the presence of human serum albumin. In this manuscript, we describe efforts to improve the polymorphic coverage of the C-3 benzoic acid chemotype through modifications at the C-28 position of the triterpenoid core. The dimethylaminoethyl amides 17 and 23 delivered improved potency toward bevirimat-resistant viruses while increasing C-24 in rat oral PK studies. (C) 2016 Elsevier Ltd. All rights reserved.
• [EN] COMPOUNDS AS IMMUNOMODULATORS OF PD-L1 INTERACTIONS<br/>[FR] COMPOSÉS À UTILISER EN TANT QU'IMMUNOMODULATEURS D'INTERACTIONS PD-L1
  申请人：[en]ASCLETIS BIOSCIENCE CO., LTD.

  公开号：WO2023019430A1

  公开（公告）日：2023-02-23

  PD-L1 inhibitors of various compound formulas, both generically and specifically are disclosed. Methods of making such PD-L1 inhibitor compounds are disclosed, both generically and specifically. Methods of using such PD-L1 inhibitor compounds singly or in combination with additional agents and compositions of such PD-L1 inhibitor compounds for the treatment of cancer and other conditions are disclosed.