N-benzyl-(2S,3R)-2,3-methanopyrrolidine | 841302-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-benzyl-(2S,3R)-2,3-methanopyrrolidine
• 英文别名: (1S,5R)-2-benzyl-2-azabicyclo[3.1.0]hexane
• CAS: 841302-40-7
• 化学式: C₁₂H₁₅N
• 分子量: 173.258
• InChiKey: JNTXVUMGVWWTGR-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-(2S,3R)-2,3-methanopyrrolidine 在 1-氯乙基氯甲酸酯 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到cis-2-azabicyclo[3.1.0]hexane hydrochloride
  参考文献：
  名称：

  Potent non-nitrile dipeptidic dipeptidyl peptidase IV inhibitors

  摘要：

  The synthesis and structure- activity relationships of novel dipeptidyl peptidase IV inhibitors replacing the classical cyanopyrrolidine P1 group with other small nitrogen heterocycles are described. A unique potency enhancement was achieved with beta-branched natural and unnatural amino acids, particularly adamantylglycines, linked to a (2S, 3R)-2,3-methanopyrrolidine based scaffold. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.090
• 作为产物：
  描述：

  N-benzyl-(L)-cis-4,5-methanoprolinenitrile 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以60%的产率得到N-benzyl-(2S,3R)-2,3-methanopyrrolidine
  参考文献：
  名称：

  [EN] ADAMANTYGLYCINE- BASED INHIBITORS OF DIPEPTIDYL PEPTIDASE IV FOR THE TREATMENT OF DIABETES
  [FR] INHIBITEURS A BASE D'ADAMANTYGLYCINE DE LA DIPEPTIDYL PEPTIDASE IV ET PROCEDES ASSOCIES

  摘要：

  公开号：

  WO2005012249A3

文献信息

• Adamantylglycine-based inhibitors of dipeptidyl peptidase IV and methods
  申请人：Hamann G. Lawrence

  公开号：US20050239839A1

  公开（公告）日：2005-10-27

  Compounds are provided having the formula (I) wherein: n is 0, 1 or 2; m is 0, 1 or 2; the sum of n+m less then or equal to 2; the dashed bonds forming a cyclopropyl ring can only be present when Y is CH; X is H or CN; Y is CH, CH 2 , CHF, CF 2 , O, S, SO, or SO 2 ; and A is adamantyl. Further provided are methods of using such compounds for the treatment of diabetes and related diseases, and to pharmaceutical compositions containing such compounds.

  提供具有公式（I）的化合物，其中：n为0、1或2；m为0、1或2；n+m的总和小于或等于2；当Y为CH时，虚线键形成环丙基环；X为H或CN；Y为CH、CH2、CHF、CF2、O、S、SO或SO2；A为金刚烷基。还提供使用这些化合物治疗糖尿病和相关疾病的方法，以及含有这些化合物的制药组合物。
• Adamantylglycine derivatives as inhibitors of dipeptidyl peptidase IV for the treatment of diabetes
  申请人：Bristol-Myers Squibb Company

  公开号：EP1997489A1

  公开（公告）日：2008-12-03

  The compounds of the present invention are adamantylglycine-based inhibitors of dipeptidyl peptidase IV (DPP-IV) and are useful for the treatment of diabetes and related diseases.

  本发明的化合物是基于金刚烷基甘氨酸的二肽基肽酶 IV（DPP-IV）抑制剂，可用于治疗糖尿病及相关疾病。
• ADAMANTYLGLYCINE- BASED INHIBITORS OF DIPEPTIDYL PEPTIDASE IV FOR THE TREATMENT OF DIABETES
  申请人：Bristol-Myers Squibb Company

  公开号：EP1658066B1

  公开（公告）日：2009-09-30
• US6995183B2
  申请人：——

  公开号：US6995183B2

  公开（公告）日：2006-02-07
• [EN] ADAMANTYGLYCINE-BASED INHIBITORS OF DIPEPTIDYL PEPTIDASE IV AND METHODS<br/>[FR] INHIBITEURS A BASE D'ADAMANTYGLYCINE DE LA DIPEPTIDYL PEPTIDASE IV ET PROCEDES ASSOCIES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2005012249A2

  公开（公告）日：2005-02-10

  Compounds are provided having the formula (I) wherein: n is 0, 1 or 2; m is 0, 1 or 2; the sum of n + m less then or equal to 2; the dashed bonds forming a cyclopropyl ring can only be present when Y is CH; X is H or CN; Y is CH, CH2, CHF, CF2, O, S, SO, or SO2; and A is adamantyl. The compounds are inhibitors of dipeptidyl peptidase IV (DPP-IV) and are useful for the treatment of diabetes and related diseases.