ethyl 5-methyl-1,2-diphenyl-1H-imidazole-4-carboxylate | 1261181-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 5-methyl-1,2-diphenyl-1H-imidazole-4-carboxylate
• 英文别名: ethyl 5-methyl-1,2-diphenylimidazole-4-carboxylate
• CAS: 1261181-00-3
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: MDYFWGUMQZVPIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  ethyl 5-methyl-1,2-diphenyl-1H-imidazole-4-carboxylate 在 N-甲基吗啉 、 lithium hydroxide monohydrate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)-2-hydroxypropyl)-5-methyl-1,2-diphenyl-1H-imidazole-4-carboxamide dihydrochloride
  参考文献：
  名称：

  Design and Synthesis of Novel Arylpiperazine Derivatives Containing the Imidazole Core Targeting 5-HT_2A Receptor and 5-HT Transporter

  摘要：

  Serotonin antagonist reuptake inhibitor (SARI) drugs that block both 5-HT2 receptors and the serotonin transporters have been developed. The human 5-HT2A/2C receptor has been implicated in several neurological conditions, and potent selective 5-HT2A/2C ligands may have therapeutic potential for treatment of CNS diseases such as depression. An imidazole moiety usually provides good pharmacokinetic properties as a drug substance, and thus considerable efforts have been devoted to develop imidazole derivatives into drug candidates. The imidazole series of compounds was evaluated against 5-HT2A/2C and serotonin reuptake inhibition. A few of the compounds in the series showed promising IC50 values and antidepressant-like effect in in vivo forced swimming test (FST). On the basis of these results, further lead optimization studies resulted in identifying promising compounds potentially for therapeutic use.

  DOI：

  10.1021/jm200682b
• 作为产物：
  描述：

  苯甲腈 在 sodium hexamethyldisilazane 、 碳酸氢钠 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 24.33h， 生成 ethyl 5-methyl-1,2-diphenyl-1H-imidazole-4-carboxylate
  参考文献：
  名称：

  Design and Synthesis of Novel Arylpiperazine Derivatives Containing the Imidazole Core Targeting 5-HT_2A Receptor and 5-HT Transporter

  摘要：

  Serotonin antagonist reuptake inhibitor (SARI) drugs that block both 5-HT2 receptors and the serotonin transporters have been developed. The human 5-HT2A/2C receptor has been implicated in several neurological conditions, and potent selective 5-HT2A/2C ligands may have therapeutic potential for treatment of CNS diseases such as depression. An imidazole moiety usually provides good pharmacokinetic properties as a drug substance, and thus considerable efforts have been devoted to develop imidazole derivatives into drug candidates. The imidazole series of compounds was evaluated against 5-HT2A/2C and serotonin reuptake inhibition. A few of the compounds in the series showed promising IC50 values and antidepressant-like effect in in vivo forced swimming test (FST). On the basis of these results, further lead optimization studies resulted in identifying promising compounds potentially for therapeutic use.

  DOI：

  10.1021/jm200682b

文献信息

• Electrochemical synthesis of 1,2,4,5-tetrasubstituted imidazoles from enamines and benzylamines
  作者：Wenxing Wang、Shuo Zhang、Guang Shi、Zhiwei Chen

  DOI：10.1039/d1ob00942g

  日期：——

  An electrochemical method for synthesizing 1,2,4,5-tetrasubstituted imidazoles was developed under undivided electrolytic conditions. This synthesis was specifically realized based on electrochemical C(sp3)–H amination via enamines and amines. Readily available starting materials were used, avoiding the use of both transition metals and oxidants. The practicability of the method lies in its broad substrate

  在不分电解条件下开发了一种合成1,2,4,5-四取代咪唑的电化学方法。该合成是基于通过烯胺和胺的电化学 C(sp 3 )-H 胺化具体实现的。使用容易获得的起始材料，避免使用过渡金属和氧化剂。该方法的实用性在于其广泛的底物适应性和为合成GABA A受体类似物提供简单的绿色途径的能力。
• NOVEL ARYLPIPERAZINE-CONTAINING IMIDAZOLE 4-CARBOXAMIDE DERIVATIVES AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
  申请人：Lee Jinhwa

  公开号：US20120115881A1

  公开（公告）日：2012-05-10

  A novel arylpiperazine-containing imidazole 4-carboxamide derivative or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising the same as an active ingredient for preventing or treating a depressive disorder are provided.

  本发明提供了一种新的含有芳基哌嗪基的咪唑-4-羧酰胺衍生物或其药学上可接受的盐，并且提供了一种以其为活性成分的制药组合物，用于预防或治疗抑郁症。
• Arylpiperazine-containing imidazole 4-carboxamide derivatives and pharmaceutical composition comprising same
  申请人：Lee Jinhwa

  公开号：US08835436B2

  公开（公告）日：2014-09-16

  A novel arylpiperazine-containing imidazole 4-carboxamide derivative or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising the same as an active ingredient for preventing or treating a depressive disorder are provided.

  本发明提供了一种新的含有芳基哌嗪基和咪唑-4-羧酰胺衍生物或其药学上可接受的盐，以及一种包含该衍生物作为活性成分的药物组合物，用于预防或治疗抑郁症。
• [EN] NOVEL ARYLPIPERAZINE-CONTAINING IMIDAZOLE 4-CARBOXAMIDE DERIVATIVES AND PHARMACEUTICAL COMPOSITION COMPRISING SAME<br/>[FR] NOUVEAUX DÉRIVÉS IMIDAZOLE-4-CARBOXAMIDE CONTENANT DE L'ARYLPIPÉRAZINE ET COMPOSITION PHARMACEUTIQUE CONTENANT CES DÉRIVÉS
  申请人：GREEN CROSS CORP

  公开号：WO2011005052A8

  公开（公告）日：2012-02-02
• A concise synthesis of highly substituted imidazoles via copper-mediated oxidative C–H functionalization
  作者：Amit N. Pandya、Devendra K. Agrawal

  DOI：10.1016/j.tetlet.2014.01.136

  日期：2014.3

  We herein report a simple and concise route for the synthesis of highly substituted imidazole derivatives via copper-mediated oxidative C-H functionalization in good to high yields. The advantage of the reaction lies in its mild reaction conditions and readily available starting materials. (C) 2014 Elsevier Ltd. All rights reserved.