氨甲酸,[2-[苯基[[2,3,4,5-四氢-2,4-二羰基-5-苯基-3-[[(苯基氨基)羰基]氨基]-1H-1,5-苯并二氮卓-1-基]乙酰基]氨基]乙基]-,苯基甲基酯 | 173908-74-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 中文名称: 氨甲酸,[2-[苯基[[2,3,4,5-四氢-2,4-二羰基-5-苯基-3-[[(苯基氨基)羰基]氨基]-1H-1,5-苯并二氮卓-1-基]乙酰基]氨基]乙基]-,苯基甲基酯
• 英文名称: benzyl N-[2-(N-[2-[2,4-dioxo-5-phenyl-3-(phenylcarbamoylamino)-1,5-benzodiazepin-1-yl]acetyl]anilino)ethyl]carbamate
• CAS: 173908-74-2
• 化学式: C₄₀H₃₆N₆O₆
• 分子量: 696.762
• InChiKey: QABGEGFXSPSCMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  964.1±65.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  52
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  氨甲酸,[2-[苯基[[2,3,4,5-四氢-2,4-二羰基-5-苯基-3-[[(苯基氨基)羰基]氨基]-1H-1,5-苯并二氮卓-1-基]乙酰基]氨基]乙基]-,苯基甲基酯 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 16.0h， 以35%的产率得到N-(2-aminoethyl)-2-[2,4-dioxo-5-phenyl-3-(phenylcarbamoylamino)-1,5-benzodiazepin-1-yl]-N-phenylacetamide
  参考文献：
  名称：

  Discovery of 1,5-Benzodiazepines with Peripheral Cholecystokinin (CCK-A) Receptor Agonist Activity. 1. Optimization of the Agonist “Trigger”

  摘要：

  Directed screening of compounds selected from the Glare registry file for contractile activity on the isolated guinea pig gallbladder (GPGB) identified a series of 1,5-benzodiazepines with peripheral cholecystokinin (CCK) receptor agonist activity. Agonist efficacy within this series was modulated by variation of substituents on the N1-anilinoacetamide moiety. Remarkably, a single methyl group confers agonist activity, with an N-isopropyl substituent providing optimal efficacy. Hydrophilic substituents on the anilino nitrogen abolish agonist activity or produce antagonists of CCK. In contrast, hydrophilic electron-donating groups at the para-position of the anilino ring enhance or maintain in vitro and in vivo agonist activity. Despite decreased affinity for the human CCK-A receptor, relative to CCK-8, some of these compounds are equipotent to CCK as anorectic agents in rats following intraperitoneal administration.

  DOI：

  10.1021/jm950626d
• 作为产物：
  描述：

  benzyl (2-(phenylamino)ethyl)carbamate 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 氨甲酸,[2-[苯基[[2,3,4,5-四氢-2,4-二羰基-5-苯基-3-[[(苯基氨基)羰基]氨基]-1H-1,5-苯并二氮卓-1-基]乙酰基]氨基]乙基]-,苯基甲基酯
  参考文献：
  名称：

  Discovery of 1,5-Benzodiazepines with Peripheral Cholecystokinin (CCK-A) Receptor Agonist Activity. 1. Optimization of the Agonist “Trigger”

  摘要：

  Directed screening of compounds selected from the Glare registry file for contractile activity on the isolated guinea pig gallbladder (GPGB) identified a series of 1,5-benzodiazepines with peripheral cholecystokinin (CCK) receptor agonist activity. Agonist efficacy within this series was modulated by variation of substituents on the N1-anilinoacetamide moiety. Remarkably, a single methyl group confers agonist activity, with an N-isopropyl substituent providing optimal efficacy. Hydrophilic substituents on the anilino nitrogen abolish agonist activity or produce antagonists of CCK. In contrast, hydrophilic electron-donating groups at the para-position of the anilino ring enhance or maintain in vitro and in vivo agonist activity. Despite decreased affinity for the human CCK-A receptor, relative to CCK-8, some of these compounds are equipotent to CCK as anorectic agents in rats following intraperitoneal administration.

  DOI：

  10.1021/jm950626d

文献信息

• Discovery of 1,5-Benzodiazepines with Peripheral Cholecystokinin (CCK-A) Receptor Agonist Activity. 1. Optimization of the Agonist “Trigger”
  作者：Christopher J. Aquino、Duncan R. Armour、Judd M. Berman、Larry S. Birkemo、Robin A. E. Carr、Dallas K. Croom、Milana Dezube、Robert W. Dougherty,、Gregory N. Ervin、Mary K. Grizzle、Julie E. Head、Gavin C. Hirst、Michael K. James、Michael F. Johnson、Laurence J. Miller、Kennedy L. Queen、Thomas J. Rimele、David N. Smith、Elizabeth E. Sugg

  DOI：10.1021/jm950626d

  日期：1996.1.1

  Directed screening of compounds selected from the Glare registry file for contractile activity on the isolated guinea pig gallbladder (GPGB) identified a series of 1,5-benzodiazepines with peripheral cholecystokinin (CCK) receptor agonist activity. Agonist efficacy within this series was modulated by variation of substituents on the N1-anilinoacetamide moiety. Remarkably, a single methyl group confers agonist activity, with an N-isopropyl substituent providing optimal efficacy. Hydrophilic substituents on the anilino nitrogen abolish agonist activity or produce antagonists of CCK. In contrast, hydrophilic electron-donating groups at the para-position of the anilino ring enhance or maintain in vitro and in vivo agonist activity. Despite decreased affinity for the human CCK-A receptor, relative to CCK-8, some of these compounds are equipotent to CCK as anorectic agents in rats following intraperitoneal administration.