2-(4-Bromophenoxy)-1-imidazol-1-ylethanone | 110009-65-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-Bromophenoxy)-1-imidazol-1-ylethanone
• CAS: 110009-65-9
• 化学式: C₁₁H₉BrN₂O₂
• 分子量: 281.109
• InChiKey: ZKXOYTGEOWJXOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-N-(4-methoxy-2-methylphenyl)acetamide 、 2-(4-Bromophenoxy)-1-imidazol-1-ylethanone 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(4-bromophenoxy)-N-[(4-methoxy-2-methylphenylcarbamoyl)methyl]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
• 作为产物：
  描述：

  (4-溴苯氧基)乙酸甲酯 在 lithium hydroxide monohydrate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 2-(4-Bromophenoxy)-1-imidazol-1-ylethanone
  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

• KHUBCHANDANI M. L.; SRIVASTAVA S. K., CURR. SCI., 56,(1987) N 6, 264-266
  作者：KHUBCHANDANI M. L.、 SRIVASTAVA S. K.

  DOI：——

  日期：——
• 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.