2-[1-({4-butylpyridin-2-yl}aminocarbonyl)cyclopentylmethyl]-4-methoxybutyric acid benzyl ester | 388631-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[1-({4-butylpyridin-2-yl}aminocarbonyl)cyclopentylmethyl]-4-methoxybutyric acid benzyl ester
• 英文别名: Benzyl 2-[[1-[(4-butylpyridin-2-yl)carbamoyl]cyclopentyl]methyl]-4-methoxybutanoate
• CAS: 388631-24-1
• 化学式: C₂₈H₃₈N₂O₄
• 分子量: 466.621
• InChiKey: CRIURYUDYIPIAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[1-({4-butylpyridin-2-yl}aminocarbonyl)cyclopentylmethyl]-4-methoxybutyric acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以97%的产率得到2-[[1-[(4-Butylpyridin-2-yl)carbamoyl]cyclopentyl]methyl]-4-methoxybutanoic acid
  参考文献：
  名称：

  Novel selective inhibitors of neutral endopeptidase for the treatment of female sexual arousal disorder

  摘要：

  A series of substituted glutaramides were synthesised using Candoxatrilat 1 as a lead and evaluated for potency against neutral endopeptidase (NEP) as a potential treatment for female sexual arousal disorder (FSAD). In this paper, we describe studies in which we were able to increase NEP activity substantially over the levels reported for previous compounds from this programme by appropriate substitution in both the P'(1) and P'(2) regions. Optimisation led to the 4-chlorophenpropylamide S-30 which was selected as a candidate for further study. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.002
• 作为产物：
  描述：

  2-(2-methoxyethyl)malonic acid dibenzyl ester 在 N-甲基吗啉 、 氢氧化钾 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 35.5h， 生成 2-[1-({4-butylpyridin-2-yl}aminocarbonyl)cyclopentylmethyl]-4-methoxybutyric acid benzyl ester
  参考文献：
  名称：

  Novel selective inhibitors of neutral endopeptidase for the treatment of female sexual arousal disorder

  摘要：

  A series of substituted glutaramides were synthesised using Candoxatrilat 1 as a lead and evaluated for potency against neutral endopeptidase (NEP) as a potential treatment for female sexual arousal disorder (FSAD). In this paper, we describe studies in which we were able to increase NEP activity substantially over the levels reported for previous compounds from this programme by appropriate substitution in both the P'(1) and P'(2) regions. Optimisation led to the 4-chlorophenpropylamide S-30 which was selected as a candidate for further study. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.002

文献信息

• Cyclopentyl-substituted glutaramide derivatives as inhibitors of neutral endopeptidase
  申请人：——

  公开号：US20020052370A1

  公开（公告）日：2002-05-02

  The invention provides compounds of formula I wherein R 1 is optionally substituted C 1-6 alkyl, optionally substituted C 3-7 cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl; n is 0, 1 or 2; and Y is —NR 18 S(O) u R 19 or a group shown below. 1

  本发明提供了式I的化合物，其中R1是可选取代的C1-6烷基，可选取代的C3-7环烷基，可选取代的芳基或可选取代的杂环基；n为0、1或2；Y为—NR18S(O)uR19或下图所示的基团1。
• Novel selective inhibitors of neutral endopeptidase for the treatment of female sexual arousal disorder
  作者：David C. Pryde、Andrew S. Cook、Denise J. Burring、Lyn H. Jones、Stephanie Foll、Michelle Y. Platts、Vivienne Sanderson、Martin Corless、Alan Stobie、Donald S. Middleton

  DOI：10.1016/j.bmc.2006.10.002

  日期：2007.1.1

  A series of substituted glutaramides were synthesised using Candoxatrilat 1 as a lead and evaluated for potency against neutral endopeptidase (NEP) as a potential treatment for female sexual arousal disorder (FSAD). In this paper, we describe studies in which we were able to increase NEP activity substantially over the levels reported for previous compounds from this programme by appropriate substitution in both the P'(1) and P'(2) regions. Optimisation led to the 4-chlorophenpropylamide S-30 which was selected as a candidate for further study. (c) 2006 Elsevier Ltd. All rights reserved.