2-(3-benzylpiperazin-1-yl)-N-[3-(methanesulfonamido)phenyl]acetamide | 481038-65-7

• 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: 2-(3-benzylpiperazin-1-yl)-N-[3-(methanesulfonamido)phenyl]acetamide
• CAS: 481038-65-7
• 化学式: C₂₀H₂₆N₄O₃S
• 分子量: 402.517
• InChiKey: ILZRCRLREJBXCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  98.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3-benzylpiperazin-1-yl)-N-[3-(methanesulfonamido)phenyl]acetamide 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-{4-[(S)-3-Amino-4-(3,4-difluoro-phenyl)-butyryl]-3-benzyl-piperazin-1-yl}-N-(3-methanesulfonylamino-phenyl)-acetamide
  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
• 作为产物：
  描述：

  N-1-Boc-3-苄基哌嗪 在 palladium dihydroxide 吡啶 、 氢气 、 镍 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 肼 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(3-benzylpiperazin-1-yl)-N-[3-(methanesulfonamido)phenyl]acetamide
  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

• Dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes
  申请人：——

  公开号：US20040236102A1

  公开（公告）日：2004-11-25

  Compounds having Formula I, including pharmaceutically acceptable salts and prodrugs thereof. (I) are inhibitors of the dipeptidyl peptidase-IV enzyme (DP-IV), and are useful in the treatment of DP-IV mediated diseases and conditions, such as non-insulin dependent diabetes mellitus. 1

  具有I式的化合物，包括其药物可接受的盐和前药。 (I)是二肽基肽酶IV酶（DP-IV）的抑制剂，可用于治疗DP-IV介导的疾病和病况，例如非胰岛素依赖性糖尿病。
• DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OF DIABETES
  申请人：Merck & Co., Inc.

  公开号：EP1406622B1

  公开（公告）日：2006-02-22
• US7253172B2
  申请人：——

  公开号：US7253172B2

  公开（公告）日：2007-08-07
• 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.