2-(4-chlorophenyl)-N-[3-(dimethylamino)propyl]-3H-imidazo[4,5-b]pyridine-3-acetamide | 118698-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-chlorophenyl)-N-[3-(dimethylamino)propyl]-3H-imidazo[4,5-b]pyridine-3-acetamide
• 英文别名: 2-[2-(4-chlorophenyl)imidazo[4,5-b]pyridin-3-yl]-N-[3-(dimethylamino)propyl]acetamide
• CAS: 118698-38-7
• 化学式: C₁₉H₂₂ClN₅O
• 分子量: 371.87
• InChiKey: OLIZFKQQLAJDBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(3-amino-2-pyridinyl)glycine ethyl ester 在 sodium hydroxide 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.88h， 生成 2-(4-chlorophenyl)-N-[3-(dimethylamino)propyl]-3H-imidazo[4,5-b]pyridine-3-acetamide
  参考文献：
  名称：

  2-Phenyl-3H-imidazo[4,5-b]pyridine-3-acetamides as nonbenzodiazepine anticonvulsants and anxiolytics

  摘要：

  A series of 2-phenyl-3H-imidazo[4,5-b]pyridine-3-acetamides were designed and synthesized as non-benzodiazepine anxiolytics based on a molecular disconnection of a typical 1,4-benzodiazepine (BZD). A number of these compounds showed submicromolar potency in a [H-3]benzodiazepine binding assay in vitro and good potency in protecting rodents against pentylenetetrazole-induced seizures. Compound 84 appears to be a selective anticonvulsant (pentylenetetrazole) agent when tested against a profile of chemically and electrically induced seizures in mice. In addition, compound 148 appears to be a selective anxiolytic/hypnotic agent on the basis of biochemical and pharmacological characterization. It appears to be a full BZD agonist as assessed by GABA shift ratio and to be effective in punishment and nonpunishment animal models of anxiety. In addition, it shows a lower side-effect profile than diazepam as assessed by rotorod neurotoxicity and potentiation of ethanol-induced sleep time in mice. The chemistry and structure-activity relationships of this series is discussed.

  DOI：

  10.1021/jm00114a007

文献信息

• TOMCZUK, BRUCE E.;SUTHERIAND, DEBORAH S.
  作者：TOMCZUK, BRUCE E.、SUTHERIAND, DEBORAH S.

  DOI：——

  日期：——
• Fused imidazoheterocyclic compounds
  申请人：A.H. ROBINS COMPANY, INCORPORATED (a Delaware corporation)

  公开号：EP0255217B1

  公开（公告）日：1992-01-22
• US4772600A
  申请人：——

  公开号：US4772600A

  公开（公告）日：1988-09-20