N-n-Propyl-α-bromacetanilid | 29877-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-n-Propyl-α-bromacetanilid
• 英文别名: 2-bromo-N-phenyl-N-propylacetamide
• CAS: 29877-08-5
• 化学式: C₁₁H₁₄BrNO
• 分子量: 256.142
• InChiKey: XGFPMXWNCXTLJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-n-Propyl-α-bromacetanilid 、 1-(2,4-dioxo-1-phenyl-2,3,4,5-tetrahydro-1H-benzo<1,4>diazepin-3-yl)-3-phenylurea 在 sodium hydride 作用下， 生成 2-[2,4-dioxo-5-phenyl-3-(phenylcarbamoylamino)-1,5-benzodiazepin-1-yl]-N-phenyl-N-propylacetamide
  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：

  N-丙基苯胺 、 溴乙酰溴 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-n-Propyl-α-bromacetanilid
  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

• HETEROAROMATIC MONOAMIDES AS OREXININ RECEPTOR ANTAGONISTS
  申请人：Knust Henner

  公开号：US20090312314A1

  公开（公告）日：2009-12-17

  The present invention is concerned with novel sulfonamides of formula wherein R 1 , R 2 , R 3 , R 4 , R 5 , Ar, Ar 1 , Ar 2 , n, o and p are as described in the description and claims. The compounds are orexin receptor antagonists that may be useful in the treatment of disorders, in which orexin pathways are involved.

  本发明涉及一种新型的磺胺类化合物，其化学式如下： 其中R1、R2、R3、R4、R5、Ar、Ar1、Ar2、n、o和p如描述和声明中所述。这些化合物是俄雷欣受体拮抗剂，可能在涉及俄雷欣途径的疾病治疗中有用。
• US8133909B2
  申请人：——

  公开号：US8133909B2

  公开（公告）日：2012-03-13
• 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.