2-{6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]quinolin-2-yl}benzoic acid | 153465-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-{6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]quinolin-2-yl}benzoic acid
• 英文别名: GA 0056；2-[6-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methylquinolin-2-yl]benzoic acid；2-[6-[(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-yl)methyl]quinolin-2-yl]benzoic acid
• CAS: 153465-66-8
• 化学式: C₂₇H₂₄N₄O₂
• 分子量: 436.513
• InChiKey: DNGCOPYVPFRMSG-UHFFFAOYSA-N

物化性质

• 沸点：
  685.4±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-{6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]quinolin-2-yl}benzoic acid 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-{2-{6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl] quinolin-2-yl}phenyl}trifluoromethanesulfonamide
  参考文献：
  名称：

  A novel trifluoromethanesulfonamidophenyl-substituted quinoline derivative, GA 0113: synthesis and pharmacological profiles

  摘要：

  The trifluoromethanesulfonamidophenyl-substituted quineline GA 0113 have been synthesized from o-nitrobenzoyl chloride via a multistep process. GA 0113 displaced specific binding of [I-125]-Sar1, Ile(8)-Ang II to AT(1) receptors in membrane from Sf9 cells. In concious normotensive dogs, GA 0113 inhibited the Ang II-induced presser response with ID50 of 0.032 mg/kg and dose-dependently increased plasma renin activity for 48 h. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(01)00383-9
• 作为产物：
  描述：

  2-乙酰苯甲酸 在 喹啉 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 硫酸 、 sodium hydride 作用下， 生成 2-{6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]quinolin-2-yl}benzoic acid
  参考文献：
  名称：

  A novel trifluoromethanesulfonamidophenyl-substituted quinoline derivative, GA 0113: synthesis and pharmacological profiles

  摘要：

  The trifluoromethanesulfonamidophenyl-substituted quineline GA 0113 have been synthesized from o-nitrobenzoyl chloride via a multistep process. GA 0113 displaced specific binding of [I-125]-Sar1, Ile(8)-Ang II to AT(1) receptors in membrane from Sf9 cells. In concious normotensive dogs, GA 0113 inhibited the Ang II-induced presser response with ID50 of 0.032 mg/kg and dose-dependently increased plasma renin activity for 48 h. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(01)00383-9

文献信息

• Process for producing 2-(carboxyphenyl)-4-quinolinecarboxylic acid
  申请人：The Green Cross Corporation

  公开号：US05780634A1

  公开（公告）日：1998-07-14

  Quinolin-2-yl benzoic acid compounds which are useful as intermediates of quinoline compounds having angiotensin II antagonist activity prepared by decarboxylating 2-(carboxyphenyl)-4-quinolinecarboxylic acid compounds in which a carboxyl group bonded to a phenyl group may be esterified, while a carboxyl group bonded to a quinoline ring is not esterified, and both rings may have one or more substituents inert to the decarboxylation reaction.

  喹啉-2-基苯甲酸化合物可作为血管紧张素II拮抗剂活性的喹啉化合物的中间体，通过脱羧2-(羧基苯基)-4-喹啉羧酸化合物制备，其中与苯基结合的羧基可酯化，而与喹啉环结合的羧基不酯化，两个环都可以有一个或多个对脱羧反应惰性的取代基。
• Process for producing 6-aminomethyl-substituted quinoline-benzoic acids
  申请人：ASAHI GLASS COMPANY LTD.

  公开号：EP0763536A1

  公开（公告）日：1997-03-19

  6-Aminomethyl-substituted quinolinebenzoic acids useful as angiotensin II antagonists are easily produced in a short step. A 2-6-(halomethyl)quinolin-2-yl}benzoic acid (1) is reacted with a secondary amine such as a 3H-imidazo[4,5-b]pyridine (2) in the presence of a base to thereby produce a 6-aminomethyl-substituted quinolinebenzoic acid (4) wherein Z may be a bromine atom, etc., R1 to R3 each may be an alkyl group, etc. and X and Y may be =N or =CH.

  易于生产的6-氨甲基取代喹啉苯甲酸可用作血管紧张素II拮抗剂，仅需一步反应即可得到。在碱存在下，2-6-(卤代甲基)喹啉-2-基}苯甲酸（1）与3H-咪唑并[4,5-b]吡啶（2）等二级胺反应，从而生成6-氨甲基取代喹啉苯甲酸（4），其中Z可以是溴原子等，R1到R3可以是烷基等，X和Y可以是= N或= CH。
• Quinoline compounds as angiotensin II antagonists
  申请人：THE GREEN CROSS CORPORATION

  公开号：EP0569013A1

  公开（公告）日：1993-11-10

  Quinoline compounds represented by the formula (1) or a salt thereof: wherein Q is represented by formulae (2) or (3) and wherein R⁶ is an acidic group, have angiotensin II antagonism and hypotensive action and are useful as an agent for the prevention and treatment of cardiovascular system diseases such as hypertension, heart failure and the like.

  式 (1) 所代表的喹啉化合物或其盐： 其中 Q 由式（2）或（3）表示 其中 R⁶ 为酸性基团，具有血管紧张素 II 拮抗和降压作用，可作为预防和治疗高血压、心力衰竭等心血管系统疾病的药物。
• Quinoline compounds
  申请人：THE GREEN CROSS CORPORATION

  公开号：EP0693478A1

  公开（公告）日：1996-01-24

  A quinoline compound represented by the formula (4): wherein R²⁵ is -COOH or -COOR¹¹; R²⁶ is -COOH or -COOR¹²; R²⁴, R²⁷ and R²⁸ may be the same or different and each independently represents a hydrogen atom, a halogen atom, a lower alkyl, alkoxy or CmF2m+1- group, wherein m is an integer of 1 to 6; and R¹¹ and R¹² are the same or different and each independently represents an lower alkyl, alkenyl, cyclo lower alkyl, aryl or aralkyl group. Processes for preparing the above compound are also provided.

  由式 (4) 代表的喹啉化合物： 其中 R²⁵ 是-COOH 或-COOR¹¹； R²⁶ 是-COOH 或-COOR¹²； R²⁴、R²⁷ 和 R²⁸ 可以相同或不同，各自独立地代表氢原子、卤素原子、低级烷基、烷氧基或 CmF2m+1- 基团，其中 m 为 1-6 的整数；以及 R¹¹ 和 R¹² 相同或不同，各自独立地代表低级烷基、烯基、环低级烷基、芳基或芳烷基。 还提供了制备上述化合物的工艺。
• Utilisation d'un antagoniste de l'angiotensine II et d'un dérivé du benzofurane à activité antiarythmique pour la préparation d'un médicament utile dans le traitement des affections cardiovasculaires
  申请人：SANOFI

  公开号：EP0752249A2

  公开（公告）日：1997-01-08

  L'invention concerne l'utilisation d'un antagoniste de l'angiotensine II et d'un dérivé du benzofurane à activité antiarythmique pour la préparation d'une composition pharmaceutique utile dans le traitement des affections cardiovasculaires, notamment dans le traitement de la défaillance cardiaque.

  本发明涉及一种血管紧张素 II 拮抗剂和一种具有抗心律失常活性的苯并呋喃衍生物用于制备治疗心血管疾病，特别是治疗心力衰竭的药物组合物。