2-amino-3-(4-chlorophenyl)-1-(4-cyclohexyl-4-[1,2,4]triazol-1-ylmethyl-piperidin-1-yl)-propan-1-one | 852319-26-7

• 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-amino-3-(4-chlorophenyl)-1-(4-cyclohexyl-4-[1,2,4]triazol-1-ylmethyl-piperidin-1-yl)-propan-1-one
• 英文别名: (2S)-2-amino-3-(4-chlorophenyl)-1-[4-cyclohexyl-4-(1,2,4-triazol-1-ylmethyl)piperidin-1-yl]propan-1-one
• CAS: 852319-26-7
• 化学式: C₂₃H₃₂ClN₅O
• 分子量: 429.993
• InChiKey: VADQRJNCGGKONM-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-3-(4-chlorophenyl)-1-(4-cyclohexyl-4-[1,2,4]triazol-1-ylmethyl-piperidin-1-yl)-propan-1-one 在 N-甲基吗啉 、 盐酸 、 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 二氯甲烷 为溶剂， 生成 (3R)-N-[(2S)-3-(4-chlorophenyl)-1-[4-cyclohexyl-4-(1,2,4-triazol-1-ylmethyl)piperidin-1-yl]-1-oxopropan-2-yl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
  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：

  去甲哌替啶 在 Rh/Al₂O₃ N-甲基吗啉 、 盐酸 、 lithium aluminium tetrahydride 、 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 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-amino-3-(4-chlorophenyl)-1-(4-cyclohexyl-4-[1,2,4]triazol-1-ylmethyl-piperidin-1-yl)-propan-1-one
  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 receptor ligands
  申请人：——

  公开号：US20040010010A1

  公开（公告）日：2004-01-15

  The present invention relates to compounds which comprise a 4-substituted piperidine ring linked to a substituted or unsubstituted hydrocarbyl ring. The compounds, including all enatiomeric and diasteriomeric forms and pharmaceutically acceptable salts thereof, have the formula: 1 wherein preferably R is substituted aryl, W 1 is a carbocyclic unit, and W 2 is a heteroatom comprising unit.

  本发明涉及包含一个与取代或未取代的烃基环相连的4-取代哌啶环的化合物。这些化合物，包括所有的对映异构体和二对映异构体形式以及其药用盐，具有以下公式：其中R最好是取代芳基，W1是一个碳环单元，W2是一个含有杂原子的单元。
• N-ACYL PIPERIDINE DERIVATIVES FOR USE AS MELANOCORTIN RECEPTOR LIGANDS IN THE TREATMENT OF FEEDING DISORDERS
  申请人：The Procter & Gamble Company

  公开号：EP1499314A1

  公开（公告）日：2005-01-26
• [EN] N-ACYL PIPERIDINE DERIVATIVES FOR USE AS MELANOCORTIN RECEPTOR LIGANDS IN THE TREATMENT OF FEEDING DISORDERS<br/>[FR] DERIVES DE N-ACYLE PIPERIDINE UTILISES COMME LIGANDS DU RECEPTEUR DE LA MELANOCORTINE DANS LE TRAITEMENT DE TROUBLES DE L'ALIMENTATION
  申请人：PROCTER & GAMBLE

  公开号：WO2003092690A1

  公开（公告）日：2003-11-13

  The present invention relates to compounds, which comprise a 4-substituted piperidine ring linked to a substituted or unsubstituted hydrocarbyl ring. The compounds, including all enatiomeric and diasteriomeric forms and pharmaceutically acceptable salts thereof, have the formula: (I): Wherein preferably R is substituted aryl, W1 is a carbocyclic unit, and W2 is a heteroatom comprising unit. The compounds are melanocortin receptor ligands useful in the treatment of eating disorders.
• Design and Pharmacology of <i>N</i>-[(3<i>R</i>)-1,2,3,4-Tetrahydroisoquinolinium- 3-ylcarbonyl]-(1<i>R</i>)-1-(4-chlorobenzyl)- 2-[4-cyclohexyl-4-(1<i>H</i>-1,2,4-triazol- 1-ylmethyl)piperidin-1-yl]-2-oxoethylamine (<b>1</b>), a Potent, Selective, Melanocortin Subtype-4 Receptor Agonist
  作者：Iyassu K. Sebhat、William J. Martin、Zhixiong Ye、Khaled Barakat、Ralph T. Mosley、David B. R. Johnston、Raman Bakshi、Brenda Palucki、David H. Weinberg、Tanya MacNeil、Rubana N. Kalyani、Rui Tang、Ralph A. Stearns、Randy R. Miller、Constantin Tamvakopoulos、Alison M. Strack、Erin McGowan、Doreen E. Cashen、Jennifer E. Drisko、Gary J. Hom、Andrew D. Howard、D. Euan MacIntyre、Lex H. T. van der Ploeg、Arthur A. Patchett、Ravi P. Nargund

  DOI：10.1021/jm025539h

  日期：2002.10.1

  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.