Benzyl 4-(cyanomethyl)-4-cyclohexylpiperidine-1-carboxylate | 475095-04-6

• 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: Benzyl 4-(cyanomethyl)-4-cyclohexylpiperidine-1-carboxylate
• CAS: 475095-04-6
• 化学式: C₂₁H₂₈N₂O₂
• 分子量: 340.466
• InChiKey: RBODINCXANPHLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Benzyl 4-(cyanomethyl)-4-cyclohexylpiperidine-1-carboxylate 在 palladium dihydroxide N-甲基吗啉 、 盐酸 、 叠氮基三甲基硅烷 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 tert-butyl N-[(2R)-3-(4-chlorophenyl)-1-[4-cyclohexyl-4-(2H-tetrazol-5-ylmethyl)piperidin-1-yl]-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Design and Pharmacology of N-[(3R)-1,2,3,4-Tetrahydroisoquinolinium- 3-ylcarbonyl]-(1R)-1-(4-chlorobenzyl)- 2-[4-cyclohexyl-4-(1H-1,2,4-triazol- 1-ylmethyl)piperidin-1-yl]-2-oxoethylamine (1), a Potent, Selective, Melanocortin Subtype-4 Receptor Agonist

  摘要：

  Synthetic and natural peptides that act as nonselective melanocortin receptor agonists have been found to be anorexigenic and to stimulate erectile activity. We report the design and development-of 1, a potent, selective (1184-fold vs MC3R, 350-fold vs MC5R), small-molecule agonist of the MC4 receptor. Pharmacological testing confirms the food intake lowering effects of MC4R agonism and suggests another role for the receptor in the stimulation of erectile activity.

  DOI：

  10.1021/jm025539h
• 作为产物：
  描述：

  环己氯化镁 在 水 、 lithium chloride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 Benzyl 4-(cyanomethyl)-4-cyclohexylpiperidine-1-carboxylate
  参考文献：
  名称：

  Design and Pharmacology of N-[(3R)-1,2,3,4-Tetrahydroisoquinolinium- 3-ylcarbonyl]-(1R)-1-(4-chlorobenzyl)- 2-[4-cyclohexyl-4-(1H-1,2,4-triazol- 1-ylmethyl)piperidin-1-yl]-2-oxoethylamine (1), a Potent, Selective, Melanocortin Subtype-4 Receptor Agonist

  摘要：

  Synthetic and natural peptides that act as nonselective melanocortin receptor agonists have been found to be anorexigenic and to stimulate erectile activity. We report the design and development-of 1, a potent, selective (1184-fold vs MC3R, 350-fold vs MC5R), small-molecule agonist of the MC4 receptor. Pharmacological testing confirms the food intake lowering effects of MC4R agonism and suggests another role for the receptor in the stimulation of erectile activity.

  DOI：

  10.1021/jm025539h

文献信息

• Melanocortin subtype 4 receptor agonists: Structure–activity relationships about the 4-alkyl piperidine core
  作者：Iyassu K. Sebhat、Yingjie Lai、Khaled Barakat、Zhixiong Ye、Rui Tang、Rubana N. Kalyani、Aurawan Vongs、Tanya MacNeil、David H. Weinberg、M. Angeles Cabello、Marta Maroto、Ana Teran、Tung M. Fong、Lex H.T. Van der Ploeg、Arthur A. Patchett、Ravi P. Nargund

  DOI：10.1016/j.bmcl.2006.11.084

  日期：2007.10

  SAR about the piperidine core in a series of MC4R agonists is described. A number of alkyl substituents that furnish compounds with good affinity and functional potency are reported. (c) 2006 Elsevier Ltd. All rights reserved.