2-(4-fluorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid | 118696-08-5

• 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-fluorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid
• 英文别名: 4-fluorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid；2-[2-(4-fluorophenyl)imidazo[4,5-b]pyridin-3-yl]acetic acid
• CAS: 118696-08-5
• 化学式: C₁₄H₁₀FN₃O₂
• 分子量: 271.251
• InChiKey: ZESAVEZXBCDSME-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C
• 沸点：
  508.1±60.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid 以44%的产率得到
  参考文献：
  名称：

  TOMCZUK, BRUCE E.;SUTHERIAND, DEBORAH S.

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(3-amino-2-pyridinyl)glycine ethyl ester 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 乙二醇 为溶剂， 反应 1.75h， 生成 2-(4-fluorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid
  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
• 作为试剂：
  描述：

  N-[3-[(4-fluorobenzoyl)amino]-2-pyridinyl]glycine ethyl ester 、 、 水 、 氢氧化钾 在 solution 、 ice water 、 水 、 2-(4-fluorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid 、 水合甲醇 作用下， 以 乙二醇 、 甲醇 为溶剂， 反应 22.0h， 以to give 45.5 g of crude title compound (88% yield)的产率得到2-(4-fluorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid
  参考文献：
  名称：

  Pharmaceutical method using fused imidazoheterocyclic compounds

  摘要：

  具有以下式子的咪唑杂环化合物：##STR1## 其中A环是吡啶，可以位于其四个位置之一；B是羰基，硫代甲基或羟甲基；Z是氢，卤素，低烷基，羟基，低烷氧基，二低烷基氨基或硝基；Ar是苯基，吡啶基，噻吩基或呋喃基；W与B形成广泛的基团组合，包括酸，酯，醇，酰胺和酮。这些化合物在治疗活体动物身体作为肌肉松弛剂，抗癫痫剂和抗焦虑剂的方法中具有中枢神经系统活性。

  公开号：

  US04948800A1

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。
• 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。
• Fused imidazopyridine compounds
  申请人：A. H. Robins Company, Incorporated

  公开号：US04824951A1

  公开（公告）日：1989-04-25

  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意一个；B是羰基，硫代甲基或羟甲基；Z是氢，卤素，较低的烷基，羟基，较低的烷氧基，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形成广泛的组合，包括酸，酯，醇，酰胺和酮。这些化合物在治疗活体动物体作为肌肉松弛剂，抗惊厥剂和抗焦虑剂时具有中枢神经系统活性。
• 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.;SUTHERLAND, DEBORAH S.
  作者：TOMCZUK, BRUCE E.、SUTHERLAND, DEBORAH S.

  DOI：——

  日期：——