2-Benzyl-4-[(3-nitro-phenylcarbamoyl)-methyl]-piperazine-1-carboxylic acid benzyl ester | 481038-62-4

• 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-Benzyl-4-[(3-nitro-phenylcarbamoyl)-methyl]-piperazine-1-carboxylic acid benzyl ester
• 英文别名: Benzyl 2-benzyl-4-{2-[(3-nitrophenyl)amino]-2-oxoethyl}piperazine-1-carboxylate；benzyl 2-benzyl-4-[2-(3-nitroanilino)-2-oxoethyl]piperazine-1-carboxylate
• CAS: 481038-62-4
• 化学式: C₂₇H₂₈N₄O₅
• 分子量: 488.543
• InChiKey: VXOISOHDZFSPBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Benzyl-4-[(3-nitro-phenylcarbamoyl)-methyl]-piperazine-1-carboxylic acid benzyl ester 在 palladium dihydroxide 吡啶 、 4-二甲氨基吡啶 、 氢气 、 镍 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 肼 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 [(S)-3-{2-Benzyl-4-[(3-methanesulfonylamino-phenylcarbamoyl)-methyl]-piperazin-1-yl}-1-(2-fluoro-benzyl)-3-oxo-propyl]-carbamic acid tert-butyl ester
  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 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Benzyl-4-[(3-nitro-phenylcarbamoyl)-methyl]-piperazine-1-carboxylic acid benzyl ester
  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：US07253172B2

  公开（公告）日：2007-08-07

  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

  具有I式的化合物，包括其药学上可接受的盐和前药：（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，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：EP1406622A2

  公开（公告）日：2004-04-14
• EP1406622A4
  申请人：——

  公开号：EP1406622A4

  公开（公告）日：2005-01-19
• US7253172B2
  申请人：——

  公开号：US7253172B2

  公开（公告）日：2007-08-07