2-(4-chloro-phenyl)-1(3)H-imidazo[4,5-b]pyridine | 952-13-6

• 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-chloro-phenyl)-1(3)H-imidazo[4,5-b]pyridine
• 英文别名: 2-p-Chlorphenyl-imidazo<4,5-b>pyridin；1H-Imidazo[4,5-b]pyridine, 2-(4-chlorophenyl)-；2-(4-chlorophenyl)-1H-imidazo[4,5-b]pyridine
• CAS: 952-13-6
• 化学式: C₁₂H₈ClN₃
• 分子量: 229.669
• InChiKey: ZCRHTMNMCCAMPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-phenyl)-1(3)H-imidazo[4,5-b]pyridine 在 sodium hydride 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 反应 5.5h， 生成 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetamide-4-oxide
  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
• 作为产物：
  描述：

  3,4-二氨基吡啶 在 sulfur 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 2-(4-chloro-phenyl)-1(3)H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  2-芳基取代的咪唑并[4,5-b]吡啶和咪唑并[4,5-c]吡啶的制备

  摘要：

  DOI：

  10.1007/bf00476381

文献信息

• Fused imidazoheterocyclic compounds and pharmaceutical compositions
  申请人：A. H. Robins Company, Inc.

  公开号：US04772600A1

  公开（公告）日：1988-09-20

  Imidazoheterocyclic compounds having the formula: ##STR1## wherein the A ring is pyridine 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 in a method for treating a living animal body as muscle relaxants, anticonvulsants and antianxiety agents.

  咪唑杂环化合物的化学式为：##STR1## 其中A环是吡啶的四个位置中的任意一个；B是羰基、硫代甲基或羟甲基；Z是氢、卤素、较低烷基、羟基、较低烷氧基、二较低烷基氨基或硝基；Ar是苯基、吡啶基、噻吩基或呋喃基；W与B形成多种组合，包括酸、酯、醇、酰胺和酮。这些化合物在治疗活体动物身体的方法中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。
• Regioselective C2-arylation of imidazo[4,5-b]pyridines
  作者：Jonathan Macdonald、Victoria Oldfield、Vassilios Bavetsias、Julian Blagg

  DOI：10.1039/c3ob27477b

  日期：——

  We show that N3-MEM-protected imidazo[4,5-b]pyridines undergo efficient C2-functionalisation via direct C–H arylation. Twenty-two substituted imidazo[4,5-b]pyridines are prepared and iterative, selective elaboration of functionalised imidazo[4,5-b]pyridines gives 2,7- and 2,6-disubstituted derivatives in good yields from common intermediates. Mechanistic observations are consistent with a concerted-metallation-deprotonation mechanism facilitated by coordination of copper(I)iodide to the imidazo[4,5-b]pyridine.

  我们的研究表明，N3-MEM 保护的咪唑并[4,5-b]吡啶可通过直接 C-H 芳基化作用进行高效的 C2 功能化。我们制备了 22 种取代的咪唑并[4,5-b]吡啶，并从普通中间体中反复选择性地阐述了官能化咪唑并[4,5-b]吡啶，得到了产率良好的 2,7- 和 2,6- 二取代衍生物。机理观察结果与通过碘化铜与咪唑并[4,5-b]吡啶的配位促进的协同金属化-质子化机理一致。
• Eco-friendly and facile synthesis of 2-substituted-1H-imidazo[4,5-b]pyridine in aqueous medium by air oxidation
  作者：Rajesh P. Kale、Mohammad U. Shaikh、Ganesh R. Jadhav、Charansingh H. Gill

  DOI：10.1016/j.tetlet.2008.12.104

  日期：2009.4

  a new environmentally-benign, convenient, and facile methodology for the synthesis of 2-substituted-1H-imidazo[4,5-b]pyridine. The reaction of 2,3-diaminopyridine with substituted aryl aldehydes in water under thermal conditions without the use of any oxidative reagent has been studied. The reaction has yielded 1H-imidazo[4,5-b]pyridine derivatives by an air oxidative cyclocondensation reaction in

  我们报告了一种新的环境友好，方便，简便的方法合成2-取代-1 H-咪唑并[4,5- b ]吡啶。研究了2,3-二氨基吡啶与取代的芳基醛在水中在热条件下不使用任何氧化剂的反应。反应产生1 H-咪唑并[4,5- b吡啶衍生物通过空气氧化环缩合反应一步一步即可获得极佳的收率。此外，合成了一系列化合物，并通过熔点，EI-MS，NMR和IR工具对其进行了表征。为了比较，参考样品通过报道的方法制备。从经济和环境的角度来看，利用水性介质，容易的反应条件，分离和纯化使这种操作非常有趣。
• Synthesis of amidines and attempted synthesis of imidazoazines by reactions of lithiated β-aminoazines with nitriles
  作者：Alan D. Redhouse、Robin J. Thompson、Basil J. Wakefield、Jacklyn A. Wardell

  DOI：10.1016/s0040-4020(01)90374-6

  日期：1992.9

  Deprotonation of 3-aminopyridine, followed by reaction of aromatic nitriles, gives N-(3-pyridyl)-benzamidines, and other β-aminoazines (pyridines, quinolines, pyrazines, pyrimidines) react similarly. Attempts to cyclise the amidines to, for example, 2-aryl-1H-imidazol[4,5-b]pyridines (5) met with limited success.

  使3-氨基吡啶去质子化，然后使芳族腈反应，得到N-（3-吡啶基）-苯甲s，而其他β-氨基嗪（吡啶，喹啉，吡嗪，嘧啶）同样反应。将the环化成例如2-芳基-1 H-咪唑[4，5- b ]吡啶（5）的尝试取得了有限的成功。
• Method of treating animals using fused imidazoheterocyclic compounds
  申请人：A. H. Robins Company, Incorporated

  公开号：US04914109A1

  公开（公告）日：1990-04-03

  Imidazoheterocyclic compounds having the formula: ##STR1## wherein the A ring is pyridine 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 in a method for treating a living animal body as muscle relaxants, anticonvulsants and antianxiety agents.

  具有以下式子的咪唑杂环化合物：##STR1## 其中A环是吡啶，可以在其四个位置中的任何一个；B是羰基，硫代甲基或羟甲基；Z是氢，卤素，低碳基，羟基，低碳氧基，二低碳基氨基或硝基；Ar是苯基，吡啶基，噻吩基或呋喃基；W与B形成各种各样的基团组合，包括酸，酯，醇，酰胺和酮。这些化合物在治疗活体动物身体的肌肉松弛剂，抗癫痫剂和抗焦虑剂的方法中具有中枢神经系统活性。