1-(1-Ethoxycarbonyl-piperidin-4-yl)-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid | 913196-04-0

• 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: 1-(1-Ethoxycarbonyl-piperidin-4-yl)-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid
• CAS: 913196-04-0
• 化学式: C₁₆H₁₉N₃O₅
• 分子量: 333.344
• InChiKey: JAKOQGLYMJCRHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  104.63
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(1-Ethoxycarbonyl-piperidin-4-yl)-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid 在 sodium hydroxide 作用下， 生成 2-Oxo-1-piperidin-4-yl-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid
  参考文献：
  名称：

  Benzodiazepine calcitonin gene-related peptide (CGRP) receptor antagonists: Optimization of the 4-substituted piperidine

  摘要：

  In our continuing effort to identify CGRP receptor antagonists for the acute treatment of migraine, we have undertaken a study to evaluate alternative 4-substituted piperidines to the lead dihydroquinazolinone 1. In this regard, we have identified the piperidinyl-azabenzimidazolone and phenylimidazolinone structures which, when incorporated into the benzodiazepine core, afford potent CGRP receptor antagonists (e.g., 18 and 29). These studies produced a potent analog (18) which overcomes the instability issues associated with the lead structure 1. A general pharmacophore for the 4-substituted piperidine component of these CGRP receptor antagonists is also presented. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.044
• 作为产物：
  描述：

  4-(4-Carboxy-2-nitro-phenylamino)-piperidine-1-carboxylic acid ethyl ester 在 盐酸 、 锌 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 1-(1-Ethoxycarbonyl-piperidin-4-yl)-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid
  参考文献：
  名称：

  Benzodiazepine calcitonin gene-related peptide (CGRP) receptor antagonists: Optimization of the 4-substituted piperidine

  摘要：

  In our continuing effort to identify CGRP receptor antagonists for the acute treatment of migraine, we have undertaken a study to evaluate alternative 4-substituted piperidines to the lead dihydroquinazolinone 1. In this regard, we have identified the piperidinyl-azabenzimidazolone and phenylimidazolinone structures which, when incorporated into the benzodiazepine core, afford potent CGRP receptor antagonists (e.g., 18 and 29). These studies produced a potent analog (18) which overcomes the instability issues associated with the lead structure 1. A general pharmacophore for the 4-substituted piperidine component of these CGRP receptor antagonists is also presented. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.044