(S)-2-(cyano-hydroxy-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | 851029-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-2-(cyano-hydroxy-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[cyano(hydroxy)methyl]pyrrolidine-1-carboxylate
• CAS: 851029-12-4
• 化学式: C₁₁H₁₈N₂O₃
• 分子量: 226.276
• InChiKey: ZPFISUQMUDCTQQ-IENPIDJESA-N

物化性质

• 沸点：
  375.2±12.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(cyano-hydroxy-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 在 盐酸羟胺 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-[(1-ethoxy-ethoxy)-[1,2,4]oxadiazole-3-yl-methyl]pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis, SAR, and X-ray structure of novel potent DPPIV inhibitors: Oxadiazolyl ketones

  摘要：

  Synthesis of a novel series of DPPIV inhibitors with 1,2,4- and 1,3,4-oxadiazolyl ketone derivatives and its structure-activity relationships are discussed. Compound 18h showed good inhibitory activity against DPPIV and favorable pharmacokinetic properties. In vivo pharmacodynamic efficacy and co-crystal structure of compound 18h with DPPIV is also described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.046
• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 二异丁基氢化铝 、 sodium hydrogensulfite 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (S)-2-(cyano-hydroxy-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis, SAR, and X-ray structure of novel potent DPPIV inhibitors: Oxadiazolyl ketones

  摘要：

  Synthesis of a novel series of DPPIV inhibitors with 1,2,4- and 1,3,4-oxadiazolyl ketone derivatives and its structure-activity relationships are discussed. Compound 18h showed good inhibitory activity against DPPIV and favorable pharmacokinetic properties. In vivo pharmacodynamic efficacy and co-crystal structure of compound 18h with DPPIV is also described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.046

文献信息

• [EN] NOVEL INHIBITORS OF DPP-IV, METHODS OF PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE AGENT<br/>[FR] INHIBITEURS DE DPP-IV, PROCEDES D'ELABORATION CORRESPONDANTS, ET COMPOSITIONS PHARMACEUTIQUES RENFERMANT CES INHIBITEURS COMME PRINCIPE ACTIF
  申请人：LG LIFE SCIENCES LTD

  公开号：WO2005037828A1

  公开（公告）日：2005-04-28

  The present invention relates to pyrrolidine-based compounds of novel structure exhibiting good inhibitory activity versus Dipeptidyl Peptidase-IV, as defined in Formula 1 of the specification, and methods of preparing the same and pharmaceutical compositions containing the same as an active agent.

  本发明涉及一种具有新结构的吡咯烷基化合物，其表现出良好的抑制二肽基肽酶-IV活性，如规范中的公式1所定义的那样，以及制备该化合物的方法和含有该化合物作为活性剂的药物组合物。
• β-Fluorinated proline derivatives: potential transition state inhibitors for proline selective serine dipeptidases
  作者：Pieter Van der Veken、Kristel Senten、István Kertèsz、Achiel Haemers、Koen Augustyns

  DOI：10.1016/s0040-4039(02)02764-8

  日期：2003.1

  Three new types of beta-fluorinated proline derivatives were synthesized as potential transition state inhibitors for proline selective serine dipeptidases. The fluorophosponate derived from protected proline was tested as a Wadsworth-Horner-Emmons reagent for the synthesis of fluoro-olefin-containing pseudodipeptides. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis, SAR, and X-ray structure of novel potent DPPIV inhibitors: Oxadiazolyl ketones
  作者：Ki Dong Koo、Min Jung Kim、Sungsub Kim、Kyoung-Hee Kim、Sang Yong Hong、Gwong-Cheung Hur、Hyeon Joo Yim、Geun Tae Kim、Hee Oon Han、O Hwan Kwon、Tae Sik Kwon、Jong Sung Koh、Chang-Seok Lee

  DOI：10.1016/j.bmcl.2007.05.046

  日期：2007.8

  Synthesis of a novel series of DPPIV inhibitors with 1,2,4- and 1,3,4-oxadiazolyl ketone derivatives and its structure-activity relationships are discussed. Compound 18h showed good inhibitory activity against DPPIV and favorable pharmacokinetic properties. In vivo pharmacodynamic efficacy and co-crystal structure of compound 18h with DPPIV is also described. (c) 2007 Elsevier Ltd. All rights reserved.