(R)-3-Amino-1-[(R)-2-(4-fluoro-benzyl)-piperazin-1-yl]-4-(2-fluoro-phenyl)-butan-1-one

• 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: (R)-3-Amino-1-[(R)-2-(4-fluoro-benzyl)-piperazin-1-yl]-4-(2-fluoro-phenyl)-butan-1-one
• 英文别名: (3R)-3-amino-4-(2-fluorophenyl)-1-[(2R)-2-[(4-fluorophenyl)methyl]piperazin-1-yl]butan-1-one
• 化学式: C₂₁H₂₅F₂N₃O
• 分子量: 373.446
• InChiKey: QHLCAZPXWSTOHD-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (R)-N-叔丁氧羰基-3-氨基-4-(2-氟苯基)丁酸 在 palladium dihydroxide 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-3-Amino-1-[(R)-2-(4-fluoro-benzyl)-piperazin-1-yl]-4-(2-fluoro-phenyl)-butan-1-one
  参考文献：
  名称：

  Substituted piperazines as novel dipeptidyl peptidase IV inhibitors

  摘要：

  Incorporation of a fluorophenyl beta-amino amide moiety into piperazine screening lead 2 has resulted in the discovery of a structurally novel series of potent and selective DP-IV inhibitors. Simplification of the molecule and incorporation of multiple fluorine atoms on the phenyl ring has provided low molecular weight analogs such as compound 32, which is a 19 nM DP-IV inhibitor with >4000-fold selectivity over QPP. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.065

文献信息

• Substituted piperazines as novel dipeptidyl peptidase IV inhibitors
  作者：Linda L. Brockunier、Jiafang He、Lawrence F. Colwell、Bahanu Habulihaz、Huaibing He、Barbara Leiting、Kathryn A. Lyons、Frank Marsilio、Reshma A. Patel、Yohannes Teffera、Joseph K. Wu、Nancy A. Thornberry、Ann E. Weber、Emma R. Parmee

  DOI：10.1016/j.bmcl.2004.06.065

  日期：2004.9

  Incorporation of a fluorophenyl beta-amino amide moiety into piperazine screening lead 2 has resulted in the discovery of a structurally novel series of potent and selective DP-IV inhibitors. Simplification of the molecule and incorporation of multiple fluorine atoms on the phenyl ring has provided low molecular weight analogs such as compound 32, which is a 19 nM DP-IV inhibitor with >4000-fold selectivity over QPP. (C) 2004 Elsevier Ltd. All rights reserved.