2-{4-[(R)-2-Amino-3-(2,4-dichloro-phenyl)-propionyl]-piperazin-1-yl}-cyclohexanecarboxylic acid ethyl ester | 866945-00-8

• 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-{4-[(R)-2-Amino-3-(2,4-dichloro-phenyl)-propionyl]-piperazin-1-yl}-cyclohexanecarboxylic acid ethyl ester
• CAS: 866945-00-8
• 化学式: C₂₂H₃₁Cl₂N₃O₃
• 分子量: 456.412
• InChiKey: GOXWVQWZWIFIIP-SKINQDTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  75.87
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-{4-[(R)-2-Amino-3-(2,4-dichloro-phenyl)-propionyl]-piperazin-1-yl}-cyclohexanecarboxylic acid ethyl ester 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-(4-{(R)-3-(2,4-Dichloro-phenyl)-2-[(piperidine-4-carbonyl)-amino]-propionyl}-piperazin-1-yl)-cyclohexanecarboxylic acid ethyl ester
  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：

  BOC-D-2,4-二氯苯丙氨酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 2-{4-[(R)-2-Amino-3-(2,4-dichloro-phenyl)-propionyl]-piperazin-1-yl}-cyclohexanecarboxylic acid ethyl ester
  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