7-bromo-5-(p-tolyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one | 5571-59-5

• 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: 7-bromo-5-(p-tolyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
• 英文别名: 7-Brom-5-p-tolyl-3H-1.4-benzodiazepin-2(1H)-on；7-Brom-5-p-tolyl-2-oxo-1.2-dihydro-1.4-benzodiazepin；7-Brom-5-<4-methyl-phenyl>-1,3-dihydro-2H-1,4-benzodiazepin-2-on；7-bromo-5-p-tolyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one；7-Bromo-5-p-tolyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one；7-bromo-5-(4-methylphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one
• CAS: 5571-59-5
• 化学式: C₁₆H₁₃BrN₂O
• 分子量: 329.196
• InChiKey: KVXRLJHLTJKYKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙醛 、 7-bromo-5-(p-tolyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以56%的产率得到7-bromo-4-propyl-5-(p-tolyl)-1,3,4,5-tetrahydro-2H-benzo[e][1,4]diazepin-2-one
  参考文献：
  名称：

  Structure–Activity Relationship Studies of Retro-1 Analogues against Shiga Toxin

  摘要：

  High-throughput screening has shown that Retro-1 inhibits ricin and Shiga toxins by diminishing their intracellular trafficking via the retrograde route, from early endosomes to the Golgi apparatus. To improve the activity of Retro-1, a structure-activity relationship (SAR) study was undertaken and yielded an analogue with a roughly 70-fold better half-maximal effective concentration (EC50) against Shiga toxin cytotoxicity measured in a cell protein synthesis assay.

  DOI：

  10.1021/acs.jmedchem.0c00298
• 作为产物：
  描述：

  2-氨基-4‘-甲基苯甲酮 在 N-溴代丁二酰亚胺(NBS) 、 氨 、 sodium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 7-bromo-5-(p-tolyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
  参考文献：
  名称：

  Structure–Activity Relationship Studies of Retro-1 Analogues against Shiga Toxin

  摘要：

  High-throughput screening has shown that Retro-1 inhibits ricin and Shiga toxins by diminishing their intracellular trafficking via the retrograde route, from early endosomes to the Golgi apparatus. To improve the activity of Retro-1, a structure-activity relationship (SAR) study was undertaken and yielded an analogue with a roughly 70-fold better half-maximal effective concentration (EC50) against Shiga toxin cytotoxicity measured in a cell protein synthesis assay.

  DOI：

  10.1021/acs.jmedchem.0c00298

文献信息

• Structure–Activity Relationship Studies of Retro-1 Analogues against Shiga Toxin
  作者：Hajer Abdelkafi、Aurélien Michau、Valérie Pons、Flora Ngadjeua、Alexandra Clerget、Lilia Ait Ouarab、David-Alexandre Buisson、David Montoir、Lucie Caramelle、Daniel Gillet、Julien Barbier、Jean-Christophe Cintrat

  DOI：10.1021/acs.jmedchem.0c00298

  日期：2020.8.13

  High-throughput screening has shown that Retro-1 inhibits ricin and Shiga toxins by diminishing their intracellular trafficking via the retrograde route, from early endosomes to the Golgi apparatus. To improve the activity of Retro-1, a structure-activity relationship (SAR) study was undertaken and yielded an analogue with a roughly 70-fold better half-maximal effective concentration (EC50) against Shiga toxin cytotoxicity measured in a cell protein synthesis assay.