2-(5-bromo-2-furanyl)-N,N-dimethyl-3H-imidazo[4,5-b]pyridine-3-acetamide | 118697-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2-(5-bromo-2-furanyl)-N,N-dimethyl-3H-imidazo[4,5-b]pyridine-3-acetamide
• 英文别名: 2-[2-(5-bromofuran-2-yl)imidazo[4,5-b]pyridin-3-yl]-N,N-dimethylacetamide
• CAS: 118697-42-0
• 化学式: C₁₄H₁₃BrN₄O₂
• 分子量: 349.187
• InChiKey: CJTMEKZTFARZRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(3-amino-2-pyridinyl)glycine ethyl ester 在 氢氧化钾 、 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 生成 2-(5-bromo-2-furanyl)-N,N-dimethyl-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

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

  公开号：EP0255217A1

  公开（公告）日：1988-02-03

  Imidazoheterocyclic compounds having the formula: wherein A is a pyridine ring in any of its four positions; B is carbonyl, thioxomethyl or hydroxymethylene; Z is hydrogen, halogen, loweralkyl, hydroxy, loweralkoxy, diloweralkylamino or nitro; Ar is phenyl, pyrido, thienyl or furanyl; and W forms a wide combination of groups with B, including acids, esters, alcohols, amides and ketones. The compounds have CNS activity and find use as muscle relaxants, anticonvulsants and antianxiety agents.

  具有以下式子的咪唑杂环化合物：其中 A 是处于四个位置中任何一个位置的吡啶环；B 是羰基、硫氧甲基或羟甲基；Z 是氢、卤素、低级烷基、羟基、低级烷氧基、稀低级烷基氨基或硝基；Ar 是苯基、吡啶基、噻吩基或呋喃基；W 与 B 形成多种基团组合，包括酸、酯、醇、酰胺和酮。 这些化合物具有中枢神经系统活性，可用作肌肉松弛剂、抗惊厥剂和抗焦虑剂。
• TOMCZUK, BRUCE E.;SUTHERIAND, DEBORAH S.
  作者：TOMCZUK, BRUCE E.、SUTHERIAND, DEBORAH S.

  DOI：——

  日期：——
• US4772600A
  申请人：——

  公开号：US4772600A

  公开（公告）日：1988-09-20
• 2-Phenyl-3H-imidazo[4,5-b]pyridine-3-acetamides as nonbenzodiazepine anticonvulsants and anxiolytics
  作者：Bruce E. Tomczuk、C. R. Taylor、L. Meredith Moses、Deborah B. Sutherland、Young S. Lo、David N. Johnson、William B. Kinnier、Brian F. Kilpatrick

  DOI：10.1021/jm00114a007

  日期：1991.10

  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.