N-{(R)-1-(4-Chloro-benzyl)-2-[4-(2-cyclohexyl-1-diethylaminomethyl-ethyl)-piperazin-1-yl]-2-oxo-ethyl}-2-(2,3-dihydro-1H-isoindol-1-yl)-acetamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: N-{(R)-1-(4-Chloro-benzyl)-2-[4-(2-cyclohexyl-1-diethylaminomethyl-ethyl)-piperazin-1-yl]-2-oxo-ethyl}-2-(2,3-dihydro-1H-isoindol-1-yl)-acetamide
• 英文别名: N-((R)-3-(4-chlorophenyl)-1-(4-(1-cyclohexyl-3-(diethylamino)propan-2-yl)piperazin-1-yl)-1-oxopropan-2-yl)-2-(isoindolin-1-yl)acetamide；N-[(2R)-3-(4-chlorophenyl)-1-[4-[1-cyclohexyl-3-(diethylamino)propan-2-yl]piperazin-1-yl]-1-oxopropan-2-yl]-2-(2,3-dihydro-1H-isoindol-1-yl)acetamide
• 化学式: C₃₆H₅₂ClN₅O₂
• 分子量: 622.294
• InChiKey: BGUKCPVRPFHBPX-BGPAPEOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  67.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(2-Cyclohexyl-1-diethylaminomethyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-{(R)-1-(4-Chloro-benzyl)-2-[4-(2-cyclohexyl-1-diethylaminomethyl-ethyl)-piperazin-1-yl]-2-oxo-ethyl}-2-(2,3-dihydro-1H-isoindol-1-yl)-acetamide
  参考文献：
  名称：

  Privileged structure based ligands for melanocortin-4 receptors—Aliphatic piperazine derivatives

  摘要：

  Aliphatic carbocyclic replacement of the benzyl group of compound I yielded compounds with high affinity for the melanocortin-4 receptor (MC4R). Compounds with a cyclohexyl group showed a consistent high affinity, while different polar groups with less basicity were good replacements for the original diethyl amines. Substitution of the polar group found in these privileged structures with an aliphatic moiety produced compounds with high affinity for MC4R. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.002

文献信息

• US7169777B2
  申请人：——

  公开号：US7169777B2

  公开（公告）日：2007-01-30
• Privileged structure based ligands for melanocortin-4 receptors—Aliphatic piperazine derivatives
  作者：Karin Briner、Iván Collado、Matthew J. Fisher、Cristina García-Paredes、Saba Husain、Steven L. Kuklish、Ana I. Mateo、Thomas P. O’Brien、Paul L. Ornstein、John Zgombick、Óscar de Frutos

  DOI：10.1016/j.bmcl.2006.04.002

  日期：2006.7

  Aliphatic carbocyclic replacement of the benzyl group of compound I yielded compounds with high affinity for the melanocortin-4 receptor (MC4R). Compounds with a cyclohexyl group showed a consistent high affinity, while different polar groups with less basicity were good replacements for the original diethyl amines. Substitution of the polar group found in these privileged structures with an aliphatic moiety produced compounds with high affinity for MC4R. (c) 2006 Elsevier Ltd. All rights reserved.