4-(2-Amino-1-cyclohexyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester | 444893-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(2-Amino-1-cyclohexyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 4-(2-amino-1-cyclohexylethyl)piperazine-1-carboxylate
• CAS: 444893-46-3
• 化学式: C₁₇H₃₃N₃O₂
• 分子量: 311.468
• InChiKey: YPAMJZKWACWRKF-UHFFFAOYSA-N

物化性质

• 沸点：
  415.6±35.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  58.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-Amino-1-cyclohexyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-(2-cyclohexyl-2-piperazin-1-ylethyl)methanesulfonamide
  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
• 作为产物：
  描述：

  环己基乙酸 在 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 氯化亚砜 、 氢溴酸 、 四丁基碘化铵 、 potassium carbonate 、 三苯基膦 、 肼 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 生成 4-(2-Amino-1-cyclohexyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester
  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

• [EN] ACYLATED PIPERAZINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR AGONISTS<br/>[FR] DERIVES DE PIPERAZINE ACYLES UTILISES COMME AGONISTES DES RECEPTEURS DE LA MELANOCORTINE 4
  申请人：MERCK & CO INC

  公开号：WO2004078716A1

  公开（公告）日：2004-09-16

  Certain novel N-acylated piperazine derivatives are agonists of the human melanocortin receptor(s) and, in particular, are selective agonists of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the activation of MC-4R, such as obesity, diabetes, sexual dysfunction, including erectile dysfunction and female sexual dysfunction.

  某些新颖的N-酰化哌嗪衍生物是人类黑素皮质素受体的激动剂，特别是人类黑素皮质素-4受体（MC-4R）的选择性激动剂。因此，它们对于治疗、控制或预防对MC-4R激活敏感的疾病和疾病是有用的，例如肥胖症、糖尿病、性功能障碍，包括勃起功能障碍和女性性功能障碍。
• Melanocortin receptor agonists
  申请人：——

  公开号：US20040116699A1

  公开（公告）日：2004-06-17

  The present invention relates to melanocortin receptor agonist of the formula I useful in the treatment of obesity, diabetes, and male and/or female sexual dysfunction 1

  本发明涉及公式I的黑色素细胞激素受体激动剂，用于治疗肥胖症、糖尿病以及男性和/或女性性功能障碍。
• WO2007/41061
  申请人：——

  公开号：——

  公开（公告）日：——
• Optimization of privileged structures for selective and potent melanocortin subtype-4 receptor ligands
  作者：Qingmei Hong、Raman K. Bakshi、James Dellureficio、Shuwen He、Zhixiong Ye、Peter H. Dobbelaar、Iyassu K. Sebhat、Liangqin Guo、Jian Liu、Tianying Jian、Rui Tang、Rubana N. Kalyani、Tanya MacNeil、Aurawan Vongs、Charles I. Rosenblum、David H. Weinberg、Qingping Peng、Constantin Tamvakopoulos、Randy R. Miller、Ralph A. Stearns、Doreen Cashen、Willian J. Martin、Airu S. Chen、Joseph M. Metzger、Howard Y. Chen、Allison M. Strack、Tung M. Fong、Euan Maclntyre、Lex H.T. Van der Ploeg、Matthew J. Wyvratt、Ravi P. Nargund

  DOI：10.1016/j.bmcl.2010.06.038

  日期：2010.8

  Design, syntheses and structure-activity relationships of N-acetylated piperazine privileged structures containing MC4R agonist compounds were described. The most potent derivatives were low nM MC4R selective full agonists. Several compounds from the series had modest pharmacokinetic properties. (C) 2010 Elsevier Ltd. All rights reserved.
• MELANOCORTIN RECEPTOR AGONISTS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1358163A1

  公开（公告）日：2003-11-05