2-amino-N-(4-bromobenzyl)acetamide | 1249577-42-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-amino-N-(4-bromobenzyl)acetamide
• 英文别名: 1-(4-bromo-benzyl)aminoacetamide；2-Amino-N-(4-bromo-benzyl)-acetamide；2-amino-N-[(4-bromophenyl)methyl]acetamide
• CAS: 1249577-42-1
• 化学式: C₉H₁₁BrN₂O
• 分子量: 243.103
• InChiKey: AVLAOJKDINCIHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-N-(4-bromobenzyl)acetamide 、 原戊酸三甲酯 在 溶剂黄146 作用下， 反应 1.5h， 生成 1-(4-bromo-benzyl)-2-butyl-1,5-dihydroimidazol-4-one
  参考文献：
  名称：

  Process for the preparation of benzylimidazole derivatives

  摘要：

  一种制备苯甲基咪唑衍生物的方法，该衍生物可用作洛卡特普制备的中间体，制备它们的新型中间体以及制备洛卡特普的方法。

  公开号：

  US20050090672A1
• 作为产物：
  描述：

  [(4-bromobenzylcarbamoyl)methyl]carbamic acid t-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-amino-N-(4-bromobenzyl)acetamide
  参考文献：
  名称：

  In silico and pharmacological screenings identify novel serine racemase inhibitors

  摘要：

  D-Serine is a coagonist of the N-methyl-D-aspartate (NMDA)-type glutamate receptor and its biosynthesis is catalyzed by serine racemase (SR). The overactivation of the NMDA receptor has been implicated in the development of neurodegenerative diseases, strokes, and epileptic seizures, thus, the inhibitors of SR have potential against these pathological states. Here, we have developed novel inhibitors of SR by in silico screening and in vitro enzyme assay. The newly developed inhibitors have lower IC50 value comparing with that of malonate, one of the standard SR inhibitor. The structural features of novel inhibitors suggest the importance of central amide structure having a phenoxy substituent in their structure for the SR inhibitory activity. The present findings suggest the importance and rational development of new drugs for diseases of NMDAR overactivation.

  DOI：

  10.1016/j.bmcl.2014.07.003

文献信息

• Ortho-Phosphinoarenesulfonamide-Mediated Staudinger Reduction of Aryl and Alkyl Azides
  作者：Xingzhuo Li、Zhenguo Wang、Wenjun Luo、Zixu Wang、Keshu Yin、Le Li

  DOI：10.3390/molecules27175707

  日期：——

  phosphine reagents are able to mediate the Staudinger reduction of both aryl and alkyl azides in either anhydrous or wet solvents. Good to excellent yields were obtained in all cases (even at a diluted concentration of 0.01 M). The formation of B-TAP, a cyclic aza-ylide, instead of phosphine oxide, eliminates the requirement of water in the Staudinger reduction. In addition, computational studies disclose

  有机叠氮化物的常规施陶丁格还原对芳基或庞大的脂肪族叠氮化物是缓慢的。此外，施陶丁格还原通常需要大量过量的水来促进氮杂叶立德中间体分解成氧化膦和胺产物。为了克服上述挑战，我们设计了一种具有邻位-SO 2 NH 2取代基的新型三芳基膦试剂2c 。在此，我们报道了这种膦试剂能够在无水或湿溶剂中介导芳基和烷基叠氮化物的施陶丁格还原。在所有情况下（即使在 0.01 M 的稀释浓度下）都获得了良好的产量。B-TAP的形成，一种环状氮杂-叶立德代替氧化膦，消除了施陶丁格还原中对水的需求。此外，计算研究表明，邻-SO 2 NH 2基团对氮杂叶立德的分子内质子化在动力学上是有利的，并且是加速芳基叠氮化物施陶丁格还原的原因。
• In silico and pharmacological screenings identify novel serine racemase inhibitors
  作者：Hisashi Mori、Ryogo Wada、Jie Li、Tetsuya Ishimoto、Mineyuki Mizuguchi、Takayuki Obita、Hiroaki Gouda、Shuichi Hirono、Naoki Toyooka

  DOI：10.1016/j.bmcl.2014.07.003

  日期：2014.8

  D-Serine is a coagonist of the N-methyl-D-aspartate (NMDA)-type glutamate receptor and its biosynthesis is catalyzed by serine racemase (SR). The overactivation of the NMDA receptor has been implicated in the development of neurodegenerative diseases, strokes, and epileptic seizures, thus, the inhibitors of SR have potential against these pathological states. Here, we have developed novel inhibitors of SR by in silico screening and in vitro enzyme assay. The newly developed inhibitors have lower IC50 value comparing with that of malonate, one of the standard SR inhibitor. The structural features of novel inhibitors suggest the importance of central amide structure having a phenoxy substituent in their structure for the SR inhibitory activity. The present findings suggest the importance and rational development of new drugs for diseases of NMDAR overactivation.
• Process for the preparation of benzylimidazole derivatives
  申请人：Allegrini Pietro

  公开号：US20050090672A1

  公开（公告）日：2005-04-28

  A process for the preparation of benzylimidazole derivatives useful as intermediates for preparation of losartan, novel intermediates for their preparation and a process for the preparation of losartan.

  一种制备苯甲基咪唑衍生物的方法，该衍生物可用作洛卡特普制备的中间体，制备它们的新型中间体以及制备洛卡特普的方法。