H-Pro-Ser-OMe | 71018-08-1

• 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: H-Pro-Ser-OMe
• 英文别名: (S)-methyl 3-hydroxy-2-((S)-pyrrolidine-2-carboxamido)propionate；methyl (2S)-3-hydroxy-2-[[(2S)-pyrrolidine-2-carbonyl]amino]propanoate
• CAS: 71018-08-1
• 化学式: C₉H₁₆N₂O₄
• 分子量: 216.237
• InChiKey: LHCPYLFIHPYSDS-BQBZGAKWSA-N

物化性质

• 沸点：
  462.7±45.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  H-Pro-Ser-OMe 在 lithium aluminium tetrahydride 、 盐酸羟胺 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 206.0h， 生成 tert-butyl (3R,8aS)-3-(hydroxymethyl)hexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate
  参考文献：
  名称：

  Synthesis of (2R, 5S)- and (2S, 5S)-2-carboxy-1,4-diaza-[4.3.0]bicyclononane as building blocks for the synthesis of new potential HIV protease inhibitors

  摘要：

  A procedure for the preparation of optically active (2R,5S)- and (2S,5S)-2-Carboxy-1,4-diaza-[4.3.0]bicyclononane is described. The method is based on the reduction of diketopiperazines obtained from cyclization of Pro-L-Ser or Pro-D-Ser and occurs without loss of enantiomeric purity. The synthesis is based on readily available starting materials and can be easily arranged for multigram scale preparations. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00241-8
• 作为产物：
  描述：

  N--(S)-serine methylester 在 氢气 作用下， 生成 H-Pro-Ser-OMe
  参考文献：
  名称：

  Human chorionic gonadotropin. III. Synthesis of a dotriacontapeptide corresponding to the C-terminal sequence 116-147 of the .BETA.-subunit of human chorionic gonadotropin (hCG).

  摘要：

  通过分步片段缩合，将五个片段[Z-Gln-Asp(OBzl)-OH、Z-Ser(Bzl)-Ser-Ser-Lys(Boc)-NHNH2、Z-Ala-Pro-Pro-NHNHBoc、Z-Ser(Bzl)-Leu-Pro-NHNHBoc 和 Z-Ser(Bzl)-Pro-Ser-NHNH2]连接到前一篇论文中报告的十六肽上，合成了该化合物。

  DOI：

  10.1248/cpb.28.2699

文献信息

• Chiral ligands containing heteroatoms. 11. Optically active 2-hydroxymethyl piperazincs as catalysts in the enantioselective addition of diethylzinc to benzaldehyde
  作者：Massimo Falorni、Michele Satta、Sandra Conti、Giampaolo Giacomelli

  DOI：10.1016/s0957-4166(00)80107-x

  日期：1993.11

  (2R,5S) and (2S,5S)-2-hydroxymethyl-5-alkyl piperazines 1–5 were prepared in good yields without any racemization. The use of these compounds as chiral catalysts for the enantioselective addition of diethylzinc to aldehydes is described. This paper reports the first example of the use of piperazine methanols in asymmetric synthesis.

  从对映体纯的丝氨酸开始，以高收率制备了一系列（2 R，5 S）和（2 S，5 S）-2-羟甲基-5-烷基哌嗪1-5，没有任何消旋作用。描述了将这些化合物用作手性催化剂以将二乙基锌对映异构地加成到醛中。本文报道了在不对称合成中使用哌嗪甲醇的第一个实例。
• Carbamoylation of Azomethine Imines via Visible-Light Photoredox Catalysis
  作者：Bianca T. Matsuo、Pedro H. R. Oliveira、José Tiago M. Correia、Márcio W. Paixão

  DOI：10.1021/acs.orglett.1c02353

  日期：2021.9.3

  versatile and robust photocatalytic methodology to install the amide functional group into azomethine imine ions is described. This protocol is distinguished by its broad scope and mild reaction conditions, which are well suited for the preparation of structurally complex compounds in the form of amino acids, peptides, and small drug-like molecules. Moreover, the generated pyrazolidinone core could

  描述了一种将酰胺官能团安装到偶氮甲碱亚胺离子中的通用且稳健的光催化方法。该协议以其广泛的范围和温和的反应条件而著称，非常适合以氨基酸、肽和类药物小分子的形式制备结构复杂的化合物。此外，生成的吡唑烷酮核心可以很容易地转化为 β-丙氨酸类似物。
• 用于治疗精神分裂症、双相障碍、认知损害和重度抑郁障碍的非典型抗精神病药和NMDA调节剂的药物组合
  申请人：西北大学

  公开号：CN108601814A

  公开（公告）日：2018-09-28

  本公开的特征在于NMDA调节剂和非典型抗精神病药的组合。本公开提供例如治疗有需要的患者的精神分裂症、双相障碍和/或认知损害病症的方法，其包括施用例如雷帕替奈和非典型抗精神病药。
• NMDA Receptors Modulators and Uses Thereof
  申请人：Moskal Joseph

  公开号：US20130035292A1

  公开（公告）日：2013-02-07

  Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of diseases and disorders, such as learning, cognitive activities, and analgesia, particularly in alleviating and/or reducing neuropathic pain. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

  本发明涉及具有增强效力的化合物，其可调节NMDA受体活性。这样的化合物可用于治疗疾病和疾病，如学习、认知活动和镇痛，特别是减轻和/或减少神经病理性疼痛。本发明还公开了口服制剂和其他药学上可接受的化合物给药形式，包括静脉给药制剂。
• NMDA receptors modulators and uses thereof
  申请人：Moskal Joseph

  公开号：US08673843B2

  公开（公告）日：2014-03-18

  Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of diseases and disorders, such as learning, cognitive activities, and analgesia, particularly in alleviating and/or reducing neuropathic pain. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

  本发明涉及具有增强的NMDA受体活性调节效能的化合物。这样的化合物可用于治疗疾病和疾病，如学习、认知活动和镇痛，特别是在缓解和/或减轻神经病性疼痛方面。还揭示了口服制剂和其他药学上可接受的化合物递送形式，包括静脉制剂。