ethyl 1-isopropyl-2-oxo-2,3-dihydro-1H-benzo[d]-imidazole-5-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: ethyl 1-isopropyl-2-oxo-2,3-dihydro-1H-benzo[d]-imidazole-5-carboxylate
• 英文别名: ethyl 2-oxo-1-propan-2-yl-3H-benzimidazole-5-carboxylate
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: RQMXBQJTNORMPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  hexa-2,4-dienoyl chloride 、 ethyl 1-isopropyl-2-oxo-2,3-dihydro-1H-benzo[d]-imidazole-5-carboxylate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  NovelN-Acylated Benzimidazolone Derivatives: Synthesis, 2D-QSAR and Targets Prediction

  摘要：

  A series of novel N-acylated benzimidazolone derivatives, were synthesized from 4-aminobenzoic acid, and their antifungal activities against Botrytis cinerea were evaluated by spore germination assay. Preliminary results indicated that most of the benzimidazolone derivatives had inhibitory effect on spore germination, among which 6-carboxylate substituted derivatives were more effective than its 5-substituted regioisomers. Furthermore, 2D-quantitative structure-activity relationship (2D-QSAR) studies revealed good predictive and statistically significant QSAR models, as well as highlighted that the activities were strongly influenced by the type of introduced acyl groups in the benzimidazolone moiety. Potential targets of the title compounds were predicted using ligand profiling and validated by molecular docking, and the results implied that the title compounds might be a new type of fatty acid synthetase inhibitor.

  DOI：

  10.5935/0103-5053.20150019
• 作为产物：
  描述：

  4-氨基-3-硝基苯甲酸乙酯 在 sodium tetrahydroborate 、 sodium dithionite 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 18.5h， 生成 ethyl 1-isopropyl-2-oxo-2,3-dihydro-1H-benzo[d]-imidazole-5-carboxylate
  参考文献：
  名称：

  NovelN-Acylated Benzimidazolone Derivatives: Synthesis, 2D-QSAR and Targets Prediction

  摘要：

  A series of novel N-acylated benzimidazolone derivatives, were synthesized from 4-aminobenzoic acid, and their antifungal activities against Botrytis cinerea were evaluated by spore germination assay. Preliminary results indicated that most of the benzimidazolone derivatives had inhibitory effect on spore germination, among which 6-carboxylate substituted derivatives were more effective than its 5-substituted regioisomers. Furthermore, 2D-quantitative structure-activity relationship (2D-QSAR) studies revealed good predictive and statistically significant QSAR models, as well as highlighted that the activities were strongly influenced by the type of introduced acyl groups in the benzimidazolone moiety. Potential targets of the title compounds were predicted using ligand profiling and validated by molecular docking, and the results implied that the title compounds might be a new type of fatty acid synthetase inhibitor.

  DOI：

  10.5935/0103-5053.20150019

文献信息

• [EN] SUBSTITUTED BENZIMIDAZOLES AS CANNABINOID MODULATOR<br/>[FR] BENZIMIDAZOLES SUBSTITUÉS EN TANT QUE MODULATEUR CANNABINOÏDE
  申请人：CADILA HEALTHCARE LTD

  公开号：WO2009116074A2

  公开（公告）日：2009-09-24

  The present invention relates to novel compounds of general formula (I), their stereoisomers, regioisomers, tautomeric forms and novel intermediates involved in their synthesis, their pharmaceutically acceptable salts, pharmaceutically acceptable solvates and pharmaceutical compositions containing them. The present invention also relates to a process of preparing novel compounds of general formula (I), their stereoisomers, regioisomers, their tautomeric forms, their pharmaceutically acceptable salts, pharmaceutically acceptable solvates, pharmaceutical compositions containing them, and novel intermediates involved in their synthesis.