tert-butyl (S)-4-(2-(1-(3-(dimethylamino)propanamido)-2-methylpropyl)-4-methylphenyl)piperazine-1-carboxylate | 1025662-39-8

• 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: tert-butyl (S)-4-(2-(1-(3-(dimethylamino)propanamido)-2-methylpropyl)-4-methylphenyl)piperazine-1-carboxylate
• CAS: 1025662-39-8
• 化学式: C₂₅H₄₂N₄O₃
• 分子量: 446.633
• InChiKey: WSTRHEBCAJUVCK-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  65.12
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-4-(2-(1-(3-(dimethylamino)propanamido)-2-methylpropyl)-4-methylphenyl)piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以100%的产率得到
  参考文献：
  名称：

  Syntheses of tetrahydrothiophenes and tetrahydrofurans and studies of their derivatives as melanocortin-4 receptor ligands

  摘要：

  Piperazinebenzylamine derivatives from trans-4-(4-chlorophenyl)tetrahydrothiophene-3-carboxylic acid 6 and its S-oxide 7 and sulfone 8, and the tetrahydrofuran 9 and its two regioisomers 11 and 13 were synthesized and studied for their binding affinities at the human melanocortin-4 receptor. These five-membered ring constrained compounds possessed similar or lower potency compared to the acyclic analogs. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.128
• 作为产物：
  描述：

  4-[2-((S)-1-amino-2-methyl-propyl)-4-methyl-phenyl]-piperazine-1-carboxylic acid tert-butyl ester 、 N,N-二甲基-Β-丙氨酸 在 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 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以60%的产率得到tert-butyl (S)-4-(2-(1-(3-(dimethylamino)propanamido)-2-methylpropyl)-4-methylphenyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Identification and characterization of pyrrolidine diastereoisomers as potent functional agonists and antagonists of the human melanocortin-4 receptor

  摘要：

  A series of trans-4-phenylpyrrolidine-3-carboxamides were synthesized and characterized as potent ligands of the human melanocortin-4 receptor. Interestingly, a pair of diastereoisomers 13b displayed potent functional agonist and antagonist activity, respectively. Thus, the 3S,4R-pyrrolidine 13b-1 possessed a K-i of 1.0 nM and an EC50 of 3.8 nM while its 3R,4S-isomer 13b-2 exhibited a K-i of 4.7 and an IC50 of 64 nM. Both compounds were highly selective over other melanocortin receptor subtypes. The MC4R agonist 13b-1 also demonstrated efficacy in a diet-induced obesity model in rats. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.115