ethyl 4-(7-chloro-2-oxo-3H-benzimidazol-1-yl)piperidine-1-carboxylate | 107618-37-1

• 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 4-(7-chloro-2-oxo-3H-benzimidazol-1-yl)piperidine-1-carboxylate
• CAS: 107618-37-1
• 化学式: C₁₅H₁₈ClN₃O₃
• 分子量: 323.779
• InChiKey: AHUCTFDERMNXRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.33
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-(7-chloro-2-oxo-3H-benzimidazol-1-yl)piperidine-1-carboxylate 在 sodium hydroxide 、 三乙胺 、 potassium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 28.0h， 生成 4-chloro-3-[1-[(6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]piperidin-4-yl]-1H-benzimidazol-2-one
  参考文献：
  名称：

  Synthesis and neuroleptic activity of a series of 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]benzimidazolone derivatives

  摘要：

  A series of 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]benzimid azolones with various substituents in both aromatic rings have been synthesized and tested for neuroleptic activity (antiapomorphine effects and [3H]spiroperidol binding) as well as extrapyramidal effects (cataleptogenic effect). A strong dependence of activity on the 5-substituent in the benzimidazolone moiety could be demonstrated. Some compounds show a large split between the desired antiapomorphine and the undesired extrapyramidal effect. From these, 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]-5-chlor obenzimidazol-2-one hydrochloride (HR 723), 12, has been selected for further preclinical and toxicological profiling.

  DOI：

  10.1021/jm00388a012
• 作为产物：
  描述：

  Ethyl 4-(2-chloro-6-nitroanilino)piperidine-1-carboxylate 在 盐酸 、 锌 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 ethyl 4-(7-chloro-2-oxo-3H-benzimidazol-1-yl)piperidine-1-carboxylate
  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

文献信息

• HENNING R.; LATTRELL R.; GARHARDS H. J.; LEVEN M., J. MED. CHEM., 30,(1987) N 5, 814-819
  作者：HENNING R.、 LATTRELL R.、 GARHARDS H. J.、 LEVEN M.

  DOI：——

  日期：——