N-(N-benzyloxycarbonyl-DL-phenylalanyl)-glycine methyl ester | 21685-41-6

• 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: N-(N-benzyloxycarbonyl-DL-phenylalanyl)-glycine methyl ester
• 英文别名: N-(N-Benzyloxycarbonyl-DL-phenylalanyl)-glycin-methylester；methyl 2-[[3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetate
• CAS: 21685-41-6
• 化学式: C₂₀H₂₂N₂O₅
• 分子量: 370.405
• InChiKey: AHHJUQKRJZLHNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(N-benzyloxycarbonyl-DL-phenylalanyl)-glycine methyl ester 在 sodium hydroxide 作用下， 生成 N-(N-benzyloxycarbonyl-DL-phenylalanyl)-glycine
  参考文献：
  名称：

  Morosowa; Shenodarowa, Zhurnal Obshchei Khimii, 1958, vol. 28, p. 1661,1667; engl. Ausg. S. 1711, 1715

  摘要：

  DOI：
• 作为产物：
  描述：

  氯甲酸乙酯 、 Cbz-DL-苯丙氨酸 在 1,4-二氧六环 作用下， 生成 N-(N-benzyloxycarbonyl-DL-phenylalanyl)-glycine methyl ester
  参考文献：
  名称：

  氨酰基夹杂物。第一次沟通。定义，概述及其与肽合成的关系†

  摘要：

  描述了一种新型的重排，其名称为氨酰基插层，其从O-氨基酰化的β-羟基酰胺衍生为β-羟酰基氨基酸酰胺。β-羟基酸可以是脂族或芳族的。由于酰胺氮可以被取代，因此该反应允许构建肽链。到现在为止，肽似乎只能通过氨酰基加成反应来获得。氨酰基插入反应显示出根本上的新途径。

  DOI：

  10.1002/hlca.19570400533

文献信息

• Peptide bond formation by intermolecular aminolysis of d-glucopyranosyl esters of amino acids
  作者：Štefica Horvat、Dina Keglević

  DOI：10.1016/s0008-6215(00)81893-5

  日期：1982.10

  HO-protected and -unprotected d -glucopyranosyl esters of N -acylamino acids (Gly, Ala, Phe) with glycine and phenylalanine methyl esters in N , N -dimethylformamide at 38° and dichloromethane at 40°, respectively, led to rupture of the C-1 ester bond and formation of the corresponding N -acyldipeptide methyl ester. The relative reactivity of the C-1 ester bond toward aminolysis was greatly influenced by

  摘要N-酰基氨基酸（Gly，Ala，Phe）的HO保护和未保护的d-吡喃葡萄糖基酯与N，N-二甲基甲酰胺中的甘氨酸和苯丙氨酸甲酯分别在38°和40°C下反应C-1酯键断裂并形成相应的N-酰基肽肽甲酯。C-1酯键对氨解的相对反应性受氨基酸亲核试剂的结构，糖苷配基侧链基团的性质以及所涉及的d-吡喃葡萄糖基酯的异头构型的影响很大。通过对两个完全乙酰化的2-O-（酰基氨基酰基）-β-d-吡喃葡萄糖进行氨解，得到与C-1相比酯在C-2上明显更低的酰化效率的证据。
• Novel Heterocyclic Substituted Carbonyl Derivatives and Their Use as Dopamine D3 Receptor Ligands
  申请人：Hendrix James A.

  公开号：US20090247509A1

  公开（公告）日：2009-10-01

  The invention relates to heterocyclic substituted carbonyl derivatives that display selective binding to dopamine D 3 receptors. In another aspect, the invention relates to a method for treating central nervous system disorders associated with the dopamine D 3 receptor activity in a patient in need of such treatment comprising administering to the subject a therapeutically effective amount of said compounds for alleviation of such disorder. The central nervous system disorders that may be treated with these compounds include Psychotic Disorders, Substance Dependence, Substance Abuse, Dyskinetic Disorders (e.g. Parkinson's Disease, Parkinsonism, Neuroleptic-Induced Tardive Dyskinesia, Gilles de la Tourette Syndrome and Huntington's Disease), Dementia, Anxiety Disorders, Sleep Disorders, Circadian Rhythm Disorders and Mood Disorders. The subject invention is also directed towards processes for the preparation of the compounds described herein as well as methods for making and using the compounds as imaging agents for dopamine D 3 receptors.

  本发明涉及杂环取代羰基衍生物，其表现出对多巴胺D3受体的选择性结合。另一方面，本发明涉及一种治疗与多巴胺D3受体活性相关的中枢神经系统疾病的方法，该方法包括向需要此类治疗的患者施用所述化合物的治疗有效量，以缓解此类疾病。这些化合物可以治疗的中枢神经系统疾病包括精神疾病、物质依赖、物质滥用、运动障碍（例如帕金森病、帕金森综合症、神经阻滞引起的迟发性运动障碍、吉尔斯-德-拉-图雷综合症和亨廷顿病）、痴呆、焦虑症、睡眠障碍、昼夜节律紊乱和情绪障碍。本发明还涉及制备所述化合物的方法以及将所述化合物作为多巴胺D3受体成像剂的制备和使用方法。
• Novel heterocyclic amide derivatives and their use as dopamine D3 receptor ligands
  申请人：Hendrix A. James

  公开号：US20070142351A1

  公开（公告）日：2007-06-21

  The invention relates to heterocyclic substituted amide derivatives that display selective binding to dopamine D 3 receptors. In another aspect, the invention relates to a method for treating central nervous system disorders associated with the dopamine D 3 receptor activity in a patient in need of such treatment comprising administering to the subject a therapeutically effective amount of said compounds for alleviation of such disorder. The central nervous system disorders that may be treated with these compounds include Psychotic Disorders, Substance Dependence, Substance Abuse, Dyskinetic Disorders (e.g. Parkinson's Disease, Parkinsonism, Neuroleptic-Induced Tardive Dyskinesia, Gilles de la Tourette Syndrome and Huntington's Disease), Dementia, Anxiety Disorders, Sleep Disorders, Circadian Rhythm Disorders and Mood Disorders. The subject invention is also directed towards processes for the preparation of the compounds described herein as well as methods for making and using the compounds as imaging agents for dopamine D 3 receptors.

  本发明涉及杂环取代酰胺衍生物，其显示对多巴胺D3受体的选择性结合。另一方面，本发明涉及一种治疗中枢神经系统疾病的方法，该疾病与需要该治疗的患者的多巴胺D3受体活性有关，包括向受试者投予所述化合物的治疗有效量以缓解该疾病。这些化合物可以治疗的中枢神经系统疾病包括精神病性障碍、物质依赖、物质滥用、运动障碍（如帕金森病、帕金森综合征、神经阻滞剂引起的迟发性运动障碍、吉尔·德·拉·图雷特综合征和亨廷顿病）、痴呆、焦虑症、睡眠障碍、昼夜节律障碍和情绪障碍。本发明还涉及制备上述化合物的过程，以及将这些化合物用作多巴胺D3受体成像剂的方法。
• Novel heterocyclic substituted carbonyl derivatives and their use as dopamine D3 receptor ligands
  申请人：Hendrix A. James

  公开号：US20070161641A1

  公开（公告）日：2007-07-12

  The invention relates to heterocyclic substituted carbonyl derivatives that display selective binding to dopamine D 3 receptors. In another aspect, the invention relates is to a method for treating central nervous system disorders associated with the dopamine D 3 receptor activity in a patient in need of such treatment comprising administering to the subject a therapeutically effective amount of said compounds for alleviation of such disorder. The central nervous system disorders that may be treated with these compounds include Psychotic Disorders, Substance Dependence, Substance Abuse, Dyskinetic Disorders (e.g. Parkinson's Disease, Parkinsonism, Neuroleptic-Induced Tardive Dyskinesia, Gilles de la Tourette Syndrome and Huntington's Disease), Dementia, Anxiety Disorders, Sleep Disorders, Circadian Rhythm Disorders and Mood Disorders. The subject invention is also directed towards processes for the preparation of the compounds described herein as well as methods for making and using the compounds as imaging agents for dopamine D 3 receptors.

  本发明涉及杂环取代羰基衍生物，其具有选择性地与多巴胺D3受体结合。另一方面，本发明涉及一种治疗中枢神经系统疾病的方法，该疾病与多巴胺D3受体活性有关，包括对患者进行治疗，向患者施用所述化合物的治疗有效量，以缓解此类疾病。这些化合物可以治疗的中枢神经系统疾病包括精神病性障碍、物质依赖、物质滥用、运动障碍（例如帕金森病、帕金森综合症、神经阻滞剂引起的迟发性运动障碍、吉尔·德·拉·图雷特综合症和亨廷顿病）、痴呆、焦虑症、睡眠障碍、昼夜节律紊乱和情绪障碍。本发明还涉及所述化合物的制备过程，以及将所述化合物作为多巴胺D3受体成像剂的制备和使用方法。
• Heterocyclic substituted carbonyl derivatives and their use as dopamine D3 receptor ligands
  申请人：Aventis Pharmaceuticals Inc.

  公开号：EP1935887A1

  公开（公告）日：2008-06-25

  The invention relates to heterocyclic substituted carbonyl derivatives of the formula I that display selective binding to dopamine D3 receptors and are useful for treating central nervous system disorders associated with the dopamine D3 receptor activity in a patient in need of such treatment comprising administering to the subject a therapeutically effective amount of said compounds for alleviation of such disorder. The central nervous system disorders that may be treated with these compounds include Psychotic Disorders, Substance Dependence, Substance Abuse, Dyskinetic Disorders (e.g. Parkinson's Disease, Parkinsonism, Neuroleptic-Induced Tardive Dyskinesia, Gilles de la Tourette Syndrome and Huntington's Disease), Dementia, Anxiety Disorders, Sleep Disorders, Circadian Rhythm Disorders and Mood Disorders. The subject invention is also directed towards processes for the preparation of the compounds described herein as well as methods for making and using the compounds as imaging agents for dopamine D3 receptors.

  本发明涉及式 I 的杂环取代的羰基衍生物 本发明涉及式 I 的杂环取代羰基衍生物，该衍生物与多巴胺 D3 受体具有选择性结合，可用于治疗需要此类治疗的患者中与多巴胺 D3 受体活性相关的中枢神经系统紊乱，包括向受试者施用治疗有效量的所述化合物以缓解此类紊乱。可用这些化合物治疗的中枢神经系统疾病包括精神障碍、药物依赖、药物滥用、运动障碍（如帕金森病、帕金森氏症、神经抑制剂诱发的迟发性运动障碍、吉勒-德拉图雷特综合征和亨廷顿氏病）、痴呆、焦虑症、睡眠障碍、昼夜节律紊乱和情绪障碍。本发明还涉及本文所述化合物的制备过程以及将这些化合物用作多巴胺 D3 受体成像剂的制备和使用方法。