N-benzyl-2-bromo-N-isopropyl-acetamide | 100140-99-6

• 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-benzyl-2-bromo-N-isopropyl-acetamide
• 英文别名: N-isopropyl-N-(phenylmethyl)-2-bromoacetamide；bromo-acetic acid-(benzyl-isopropyl-amide)；Brom-essigsaeure-(benzyl-isopropyl-amid)；N-benzyl-2-bromo-N-propan-2-ylacetamide
• CAS: 100140-99-6
• 化学式: C₁₂H₁₆BrNO
• 分子量: 270.169
• InChiKey: WJPVFFBRYJACFF-UHFFFAOYSA-N

物化性质

• 沸点：
  124-136 °C(Press: 0.2 Torr)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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-benzyl-2-bromo-N-isopropyl-acetamide 、 1-phenyl-4H-<1,2,4>-triazolo<4,3-a><1,5>benzodiazepin-5(6H)-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 24.0h， 生成 N-benzyl-N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-acetamide
  参考文献：
  名称：

  Tetraazabenzo[e]azulene derivatives and analogs thereof

  摘要：

  这项发明涉及公式（I）中的CCK-A激动剂， 其中R1-R4，A，B，X，D，E和G如规范中所定义，以及包含这些化合物的药物组合物和这些化合物和组合物的使用方法。这些化合物在治疗肥胖症方面是有用的。

  公开号：

  US20050267100A1
• 作为产物：
  描述：

  N-苄基异丙胺 、 溴乙酰溴 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 N-benzyl-2-bromo-N-isopropyl-acetamide
  参考文献：
  名称：

  Tetraazabenzo[e]azulene derivatives and analogs thereof

  摘要：

  这项发明涉及公式（I）中的CCK-A激动剂， 其中R1-R4，A，B，X，D，E和G如规范中所定义，以及包含这些化合物的药物组合物和这些化合物和组合物的使用方法。这些化合物在治疗肥胖症方面是有用的。

  公开号：

  US20050267100A1
• 作为试剂：
  描述：

  N-benzyl-2-bromo-N-isopropyl-acetamide 、 1-phenyl-4H-<1,2,4>-triazolo<4,3-a><1,5>benzodiazepin-5(6H)-one 在 N-benzyl-2-bromo-N-isopropyl-acetamide 作用下， 生成 N-benzyl-N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-acetamide
  参考文献：
  名称：

  Bioorganic Medicinal Chemistry Letters 2010, 20, 6797-6801

  摘要：

  DOI：

文献信息

• TETRAAZABENZO[E]AZULENE DERIVATIVES AND ANALOGS THEREOF
  申请人：Elliott L. Richard

  公开号：US20070265193A1

  公开（公告）日：2007-11-15

  This invention relates to CCK-A agonists of Formula (I) wherein R 1 -R 4 , A, B, X, D, E and G are as defined in the specification, as well as, among other things, pharmaceutical compositions containing the compounds and methods of use of the compounds and compositions. The compounds are useful in treating diabetes.

  本发明涉及式(I)的CCK-A激动剂，其中R1-R4，A，B，X，D，E和G如规范中所定义，以及包含该化合物的药物组合物和使用该化合物和组合物的方法，该化合物在治疗糖尿病方面有用。
• Synthesis and Structure–Activity Relationship Studies in Translocator Protein Ligands Based on a Pyrazolo[3,4-<i>b</i>]quinoline Scaffold
  作者：Andrea Cappelli、Giulia Bini、Salvatore Valenti、Germano Giuliani、Marco Paolino、Maurizio Anzini、Salvatore Vomero、Gianluca Giorgi、Antonio Giordani、Luigi Piero Stasi、Francesco Makovec、Carla Ghelardini、Lorenzo Di Cesare Mannelli、Alessandra Concas、Patrizia Porcu、Giovanni Biggio

  DOI：10.1021/jm200770f

  日期：2011.10.27

  As a further development of our large program focused on the medicinal chemistry of translocator protein [TSPO (18 kDa)] ligands, a new class of compounds related to alpidem has been designed using SSR180575, emapunil, and previously published pyrrolo[3,4-b]quinoline derivatives 9 as templates. The designed compounds were synthesized by alkylation of the easily accessible 4-methyl-2-phenyl-1H-pyrazolo[3,4-b]quinolin-3(2H)-one derivatives 13-15 with the required bromoacetamides. Along with the expected 2-(4-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazolo[3,4-b]quinolin-1-yl)acetamide derivatives 10, 2-(4-methyl-3-oxo-2-phenyl-2H-pyrazolo[3,4-b]quinolin-9(3H)-yl)acetamide isomers 11 were isolated and characterized. The high TSPO affinity shown by new pyrazolo[3,4-b]quinoline derivatives 10 and especially 11 leads the way to further expand the chemical diversity in TSPO ligands and provides new templates and structure affinity relationship data potentially useful in the design of new anxiolytic and neuroprotective agents.
• Discovery of N-benzyl-2-[(4S)-4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-6H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-6-yl]-N-isopropylacetamide, an orally active, gut-selective CCK1 receptor agonist for the potential treatment of obesity
  作者：Richard L. Elliott、Kimberly O. Cameron、Janice E. Chin、Jeremy A. Bartlett、Elena E. Beretta、Yue Chen、Paul Da Silva Jardine、Jeffrey S. Dubins、Melissa L. Gillaspy、Diane M. Hargrove、Amit S. Kalgutkar、Janet A. LaFlamme、Mary E. Lame、Kelly A. Martin、Tristan S. Maurer、Nancy A. Nardone、Robert M. Oliver、Dennis O. Scott、Dexue Sun、Andrew G. Swick、Catherine E. Trebino、Yingxin Zhang

  DOI：10.1016/j.bmcl.2010.08.115

  日期：2010.11

  We describe the design, synthesis, and structure-activity relationships of triazolobenzodiazepinone CCK1 receptor agonists. Analogs in this series demonstrate potent agonist activity as measured by in vitro and in vivo assays for CCK1 agonism. Our efforts resulted in the identification of compound 4a which significantly reduced food intake with minimal systemic exposure in rodents. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.
• Microwave-Enhanced Synthesis of Phosphonoacetamides
  作者：Nadia Gruber、María C. Mollo、Mariana Zani、Liliana R. Orelli

  DOI：10.1080/00397911.2010.530377

  日期：2012.3.1

  An efficient microwave protocol is described for the Michaelis-Arbuzov synthesis of secondary and tertiary N-aryl (and alkyl) (diethylphosphono) acetamides 1, by reaction of chloro- and bromoacetamides with triethyl phosphite in the presence of catalytic amounts of sodium iodide. Remarkable acceleration of the reaction (minutes vs. several hours) over conventional heating was achieved, together with improved product yields and purity, when bromoacetamides were employed as the substrates. Chloroacetamides were comparatively less reactive, leading to satisfactory yields only when a high excess of the reagent was employed.