trans-2-{4-[(R)-2-acetylamino-3-(2,4-dichlorophenyl)propionyl]piperazin-1-yl}cyclohexanecarboxylic acid | 866947-08-2

• 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: trans-2-{4-[(R)-2-acetylamino-3-(2,4-dichlorophenyl)propionyl]piperazin-1-yl}cyclohexanecarboxylic acid
• CAS: 866947-08-2
• 化学式: C₂₂H₂₉Cl₂N₃O₄
• 分子量: 470.396
• InChiKey: LFVKLGRPOZZDCN-SKINQDTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  89.95
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  trans-2-{4-[(R)-2-acetylamino-3-(2,4-dichlorophenyl)propionyl]piperazin-1-yl}cyclohexanecarboxylic acid 、 噻吩乙胺 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Potent and orally active non-peptide antagonists of the human melanocortin-4 receptor based on a series of trans-2-disubstituted cyclohexylpiperazines

  摘要：

  The melanocortin-4 receptor (MC4R) plays an important role in the regulation of energy homeostasis. Recent studies have shown that blockade of the MC4R reverses tumor-induced weight loss in mice. Herein, we describe the synthesis and identification of potent and selective non-peptide antagonists of the human MC4R from a series of 2-ethoxycarbonylcyclohexyl-piperazines. Compound 12i was found to possess low nanomolar affinity for the MC4R, and exhibit oral bioavailability in rats. More importantly, when administered orally to mice (10 mg/kg), it led to statistically significant increases in food intake over a 24-h period. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.071
• 作为产物：
  描述：

  2-环己酮甲酸乙酯 在 盐酸 、 氢氧化钾 、 sodium ethanolate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 trans-2-{4-[(R)-2-acetylamino-3-(2,4-dichlorophenyl)propionyl]piperazin-1-yl}cyclohexanecarboxylic acid
  参考文献：
  名称：

  Potent and orally active non-peptide antagonists of the human melanocortin-4 receptor based on a series of trans-2-disubstituted cyclohexylpiperazines

  摘要：

  The melanocortin-4 receptor (MC4R) plays an important role in the regulation of energy homeostasis. Recent studies have shown that blockade of the MC4R reverses tumor-induced weight loss in mice. Herein, we describe the synthesis and identification of potent and selective non-peptide antagonists of the human MC4R from a series of 2-ethoxycarbonylcyclohexyl-piperazines. Compound 12i was found to possess low nanomolar affinity for the MC4R, and exhibit oral bioavailability in rats. More importantly, when administered orally to mice (10 mg/kg), it led to statistically significant increases in food intake over a 24-h period. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.071