3-(4-aminobutyl)-1-benzyl-8-chloro-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione | 1013314-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 3-(4-aminobutyl)-1-benzyl-8-chloro-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione
• 英文别名: (3S)-3-(4-aminobutyl)-1-benzyl-8-chloro-3,4-dihydro-1,4-benzodiazepine-2,5-dione
• CAS: 1013314-29-8
• 化学式: C₂₀H₂₂ClN₃O₂
• 分子量: 371.867
• InChiKey: YJDGJKULBWAHHK-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  溴甲苯 、 N-Boc-L-赖氨酸甲酯盐酸盐 、 2-氨基-4-氯苯甲酸 生成 3-(4-aminobutyl)-1-benzyl-8-chloro-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione
  参考文献：
  名称：

  The 1,4-Benzodiazepine-2,5-dione Small Molecule Template Results in Melanocortin Receptor Agonists with Nanomolar Potencies

  摘要：

  The melanocortin system consists of five seven-transmembrane spanning G-protein coupled receptors (MC1-5) that are stimulated by endogenous agonists and antagonized by the only two known endogenous antagonists of GPCRs, agouti and agouti-related protein (AGRP). These receptors have been associated with many physiological functions, including the involvement of the MC4R in feeding behavior and energy homeostasis, making this system an attractive target for the treatment of obesity. Small-molecule mimetics of endogenous ligands may result in the development of compounds with properties more suitable for use as therapeutic agents. The research presented herein involves the synthesis and analysis of 12 melanocortin receptor agonists using the 1,4-benzodiazepine-2,5-dione template and is the first report of these derivatives as melanocortin receptor agonists. Structure-activity relationship studies using this privileged structure, template has resulted in molecules with molecular weights around 400 that possess nanomolar agonist potency at the melanocortin receptors examined in this study.

  DOI：

  10.1021/jm701303z

文献信息

• The 1,4-Benzodiazepine-2,5-dione Small Molecule Template Results in Melanocortin Receptor Agonists with Nanomolar Potencies
  作者：Christine G. Joseph、Krista R. Wilson、Michael S. Wood、Nicholas B. Sorenson、Dong V. Phan、Zhimin Xiang、Rachel M. Witek、Carrie Haskell-Luevano

  DOI：10.1021/jm701303z

  日期：2008.3.13

  The melanocortin system consists of five seven-transmembrane spanning G-protein coupled receptors (MC1-5) that are stimulated by endogenous agonists and antagonized by the only two known endogenous antagonists of GPCRs, agouti and agouti-related protein (AGRP). These receptors have been associated with many physiological functions, including the involvement of the MC4R in feeding behavior and energy homeostasis, making this system an attractive target for the treatment of obesity. Small-molecule mimetics of endogenous ligands may result in the development of compounds with properties more suitable for use as therapeutic agents. The research presented herein involves the synthesis and analysis of 12 melanocortin receptor agonists using the 1,4-benzodiazepine-2,5-dione template and is the first report of these derivatives as melanocortin receptor agonists. Structure-activity relationship studies using this privileged structure, template has resulted in molecules with molecular weights around 400 that possess nanomolar agonist potency at the melanocortin receptors examined in this study.