(S)-(4-methyl-1,4-diazepan-1-yl)(pyrrolidin-2-yl)methanethione | 479234-57-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂卓
• 英文名称: (S)-(4-methyl-1,4-diazepan-1-yl)(pyrrolidin-2-yl)methanethione
• 英文别名: (4-methyl-1,4-diazepan-1-yl)-[(2S)-pyrrolidin-2-yl]methanethione
• CAS: 479234-57-6
• 化学式: C₁₁H₂₁N₃S
• 分子量: 227.374
• InChiKey: AWJYUWJRGJYWNP-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  50.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-(氨基甲基)-3-甲基苯基)(2,3,4,5-四氢-1H-苯并[B]氮杂-1-基)甲酮 、 N,N'-羰基二咪唑 、 (S)-(4-methyl-1,4-diazepan-1-yl)(pyrrolidin-2-yl)methanethione 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以95%的产率得到(2S)-N-[2-methyl-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-ylcarbonyl)benzyl]-2-[(4-methyl-1,4-diazepan-1-yl)carbonothioyl]-pyrrolidine-1-carboxamide
  参考文献：
  名称：

  Subtlety of the Structure−Affinity and Structure−Efficacy Relationships around a Nonpeptide Oxytocin Receptor Agonist

  摘要：

  Very Few nonpeptide oxytocin agonists have currently been reported, and none of them seem suitable for the in vivo investigation of the oxytocin mediated functions. In all attempt to rationalize the design of better tools, we have systematically studied the structural determinants of the affinity and efficacy of representative ligands of the V-1a, V-2, and OT receptor subtypes. Despite apparently obvious similarity between the ligand structures on one hand, and between the receptor subtypes on the other hand, the binding affinity and the functional activity profiles of truncated and hybrid ligands highlight the subtlety of ligand-receptor interactions for obtaining nonpeptide OT receptor agonists.

  DOI：

  10.1021/jm901084f
• 作为产物：
  描述：

  benzyl (S)-2-(4-methyl-1,4-diazepane-1-carbonothioyl)pyrrolidine-1-carboxylate 在 氢溴酸 、 溶剂黄146 作用下， 生成 (S)-(4-methyl-1,4-diazepan-1-yl)(pyrrolidin-2-yl)methanethione
  参考文献：
  名称：

  Non-peptide oxytocin agonists

  摘要：

  A library of compounds targeted to the vasopressin/oxytocin family of receptors was screened for activity at a cloned human oxytocin receptor using a reporter gene assay. Potency and selectivity were optimised to afford compound 39, EC50 = 33 nM. This series of compounds represents the first disclosed, non-peptide, low molecular weight agonists of the hormone oxytocin (OT). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.107

文献信息

• Pyrazolo[1,4]diazepines as non-peptidic probes of the oxytocin and vasopressin receptors
  作者：Tristan A. Reekie、Iain S. McGregor、Michael Kassiou

  DOI：10.1016/j.tetlet.2014.06.022

  日期：2014.8

  An improved synthesis of differently substituted pyrazolo[1,4]diazepine compounds is reported. In addition, we have used this methodology to obtain non-peptidic compounds to probe the oxytocin and vasopressin receptors. (C) 2014 Elsevier Ltd. All rights reserved.