2-(4-氰基苄基)肼羧酸叔丁酯 | 149267-90-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-氰基苄基)肼羧酸叔丁酯
• 英文名称: tert-butyl 2-(4-cyanobenzyl)-1-hydrazine carboxylate
• 英文别名: tert-butyl 2-(4-cyanobenzyl)hydrazinecarboxylate；tert-butyl-3-(4-cyanophenyl-methyl)-carbazate；tert-butyl N-[(4-cyanophenyl)methylamino]carbamate
• CAS: 149267-90-3
• 化学式: C₁₃H₁₇N₃O₂
• 分子量: 247.297
• InChiKey: POKKJVNZXJKYSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  74.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-氰基苄基)肼羧酸叔丁酯 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 N'-(4-cyanobenzyl)-N'-[(4-methyl-1-piperidinyl)carbonyl]-2-naphthalenesulfonohydrazide
  参考文献：
  名称：

  凝血酶抑制剂与氮杂苯丙氨酸支架的设计与构效关系：通过P2优化提高效能和选择性。

  摘要：

  理论和结构研究，然后进行定向合成和体外生物学测试，使我们获得了新型的非共价凝血酶假肽抑制剂。我们已经将氮杂肽支架整合到经典三肽D-Phe-Pro-Arg抑制剂结构的中心部分，从而从分子中消除了一个立体定位中心。设计了一系列化合物以优化凝血酶S2口袋的占用率。在P2处增加的疏水性增强了对该活性位点S2口袋的贴合性。在本文中，我们还报告了这些抑制剂在溶液中的结构以及活性位点中抑制剂的构象分析，以评估氮官能团取代中心α-CH的后果。

  DOI：

  10.1016/s0968-0896(01)00202-4
• 作为产物：
  描述：

  肼基甲酸叔丁酯 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2-(4-氰基苄基)肼羧酸叔丁酯
  参考文献：
  名称：

  Thrombin inhibitors built on an azaphenylalanine scaffold

  摘要：

  A series of azaphenylalanine derivatives were investigated as novel thrombin inhibitors based on the prodrug principle. By systematic structural modifications we have identified optimal groups for this series that led us to potent inhibitors of thrombin incorporating the benzamidine fragment at the PI position, and their potentially orally active benzamidoxime prodrugs. The binding modes in the thrombin active site of two representative compounds were identified by X-ray crystallographic analysis. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2003.12.083

文献信息

• Design and structure–activity relationship of thrombin inhibitors with an azaphenylalanine scaffold: potency and selectivity enhancements via P2 optimization
  作者：A Zega、G Mlinšek、P Šepic、S Golič Grdadolnik、T Šolmajer、T.B Tschopp、B Steiner、D Kikelj、U Urleb

  DOI：10.1016/s0968-0896(01)00202-4

  日期：2001.10

  provides an enhanced fit into this active site S2 pocket. In the present paper, we also report on the structure of these inhibitors in solution and conformational analysis of inhibitors in the active site in order to asses the consequences of the replacement of the central alpha-CH by a nitrogen functionality. In vitro biological testing of the designed inhibitors shows that elimination of R, S stereoisomerism

  理论和结构研究，然后进行定向合成和体外生物学测试，使我们获得了新型的非共价凝血酶假肽抑制剂。我们已经将氮杂肽支架整合到经典三肽D-Phe-Pro-Arg抑制剂结构的中心部分，从而从分子中消除了一个立体定位中心。设计了一系列化合物以优化凝血酶S2口袋的占用率。在P2处增加的疏水性增强了对该活性位点S2口袋的贴合性。在本文中，我们还报告了这些抑制剂在溶液中的结构以及活性位点中抑制剂的构象分析，以评估氮官能团取代中心α-CH的后果。
• [EN] AZAPHENYLALANINE DERIVATIVES AND THEIR USE AS ANTITHROMBOTIC AGENTS<br/>[FR] DERIVES D'AZAPHENYLALANINE ET LEUR UTILISATION EN TANT QU'AGENTS ANTITHROMBONTIQUES
  申请人：LEK PHARMACEUTICALS

  公开号：WO2004067522A1

  公开（公告）日：2004-08-12

  Novel azaphenylalanine derivatives of the formula I and pharmaceutically acceptable salts thereof are described wherein the substituents have the meanings as specified in the description. The compounds are useful as anticoagulants.

  描述了一种公式I的新型假丝氨酸衍生物和其药用可接受的盐，其中取代基的含义如描述中所指定。这些化合物可用作抗凝剂。
• Novel Super-Resolution Imaging Compositions and Methods Using Same
  申请人：Yale University

  公开号：US20160115180A1

  公开（公告）日：2016-04-28

  The invention provides compositions that may be used for imaging intracellular structures. The invention further provides methods of imaging intracellular structures. In certain embodiments, the compositions of the invention include trans-cyclooctene-containing ceramide lipids and tetrazine-containing rhodamine-related dyes.

  该发明提供了可用于成像细胞内结构的组合物。该发明进一步提供了成像细胞内结构的方法。在某些实施例中，该发明的组合物包括含有反式环辛烯的鞘氨醇脂质和含有四氮唑的罗丹明相关染料。
• Methods of treating alzheimer's disease
  申请人：Schostarez Heinrich

  公开号：US20050130941A1

  公开（公告）日：2005-06-16

  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 hydrazine compounds of formula (I) wherein the variables R 1 -R 9 are defined herein.

  本发明涉及使用式(I)中变量R1-R9所定义的肼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，抑制A beta肽在哺乳动物体内的沉积。
• Aza-Peptide Analogs as Potent Human Immunodeficiency Virus Type-1 Protease Inhibitors with Oral Bioavailability
  作者：Alexander Fässler、Guido Bold、Hans-Georg Capraro、Robert Cozens、Jürgen Mestan、Bernard Poncioni、Johannes Rösel、Marina Tintelnot-Blomley、Marc Lang

  DOI：10.1021/jm960022p

  日期：1996.1.1

  A series of aza-peptide analogs with a (hydroxyethyl)hydrazine isostere has been synthesized as HIV-1 protease inhibitors using a simple synthetic scheme. Structure-activity studies based on the X-ray of a previously described inhibitor-enzyme complex led to potent inhibitors with antiviral activity in the low-nanomolar range. The S-configuration of the transition-state hydroxyl group was preferred in this series. Small modifications of the P2P3 and P-2'P-3' substituents had little effect on enzyme inhibition but greatly influenced the pharmacokinetic profile. As a result of these studies, the symmetrically acylated compound 8a and its close analog 24a bearing a methyl carbamate in P-3 and an ethyl carbamate in P-3' position were identified as potent inhibitors with plasma concentrations exceeding antiviral ED(50) values 150-fold following oral application in mice.