8-甲氧基-2-氧代-1H-喹啉-3-羧酸 | 169321-92-0

• 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
• 中文名称: 8-甲氧基-2-氧代-1H-喹啉-3-羧酸
• 英文名称: 8-methoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid
• 英文别名: 8‑methoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid；8-methoxy-2-oxo-1H-quinoline-3-carboxylic acid
• CAS: 169321-92-0
• 化学式: C₁₁H₉NO₄
• 分子量: 219.197
• InChiKey: ZOCSBJTWWJARJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-甲氧基-2-氧代-1H-喹啉-3-羧酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Design, synthesis and evaluation the bioactivities of novel 8‑methoxy-1-azacoumarin-3-carboxamide derivatives as anti-diabetic agents

  摘要：

  DOI：

  10.1016/j.molstruc.2023.136486
• 作为产物：
  描述：

  8-甲氧基-2-氧代-2H-色烯-3-羧酸乙酯 在 potassium carbonate 、 氨 作用下， 以 乙醇 为溶剂， 以61 %的产率得到8-甲氧基-2-氧代-1H-喹啉-3-羧酸
  参考文献：
  名称：

  Design, synthesis and evaluation the bioactivities of novel 8‑methoxy-1-azacoumarin-3-carboxamide derivatives as anti-diabetic agents

  摘要：

  DOI：

  10.1016/j.molstruc.2023.136486

文献信息

• Isoindoline derivatives
  申请人：KYORIN PHARMACEUTICAL CO., LTD.

  公开号：EP0443498A1

  公开（公告）日：1991-08-28

  Optically active 8-methoxyquinolonecarboxylic acids represented by the formula (I) wherein R1 is lower alkyl have been found to possess potent antibacterial activity against both Gram-negative and Gram-positive bacteria. The compounds may be synthesized from novel optically active intermediates.

  光学活性的8-甲氧基喹啉羧酸（化学式为(I)，其中R1为低碳烷基）已被发现具有强大的抗细菌活性，对革兰氏阴性和革兰氏阳性细菌均有效。这些化合物可以从新颖的光学活性中间体合成。
• CIS-SUBSTITUTED FLUOROMETHYLPYRROLIDINE DERIVATIVE
  申请人：——

  公开号：US20020072608A1

  公开（公告）日：2002-06-13

  An antibacterial drug having potent antibacterial activities upon various bacteria including resistant strains and high safety is disclosed, which comprises as an active ingredient, quinolone derivatives represented by the following formula (I), its salts or hydrates thereof: 1 wherein R 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R 2 represents a halogenomethoxyl group or an alkoxyl group, R 3 represents an alkyl group, an alkenyl group, a halogenoalkyl group, a cyclic alkyl group, a heteroaryl group, an alkoxyl group or an alkylamino group, and R 4 represents a hydrogen atom, a phenyl group, an acetoxymethyl group, a pivaloyloxymethyl group, an ethoxycarbonyl group, a choline group, a dimethylaminoethyl group, a 5-indanyl group, a phthalidinyl group, a 5-alkyl-2-oxo-1,3-dioxol-4-ylmethyl group, 3-acetoxy-2-oxobutyl group, an alkyl group, an alkoxylmethyl group or a phenylalkyl group. These substituents may further have additional substituents.

  揭示了一种具有对各种细菌具有强效抗菌活性，包括耐药菌株和高安全性的抗菌药物，其包括以下式(I)所代表的喹诺酮衍生物作为活性成分，其盐或水合物：其中R1代表氢原子或具有1至6个碳原子的烷基基团，R2代表卤代甲氧基基团或烷氧基基团，R3代表烷基基团、烯基基团、卤代烷基基团、环烷基基团、杂环芳基团、烷氧基基团或烷基氨基基团，R4代表氢原子、苯基、乙酰氧甲基基团、戊二酰氧甲基基团、乙氧羰基基团、胆碱基团、二甲氨基乙基基团、5-茚基基团、邻苯二甲酰基基团、5-烷基-2-氧代-1,3-二氧杂环戊-4-基甲基基团、3-乙酰氧基-2-氧代丁基基团、烷基基团、烷氧基甲基基团或苯基烷基基团。这些取代基还可能具有额外的取代基。
• 8-METHOXYQUINOLONECARBOXYLIC ACID DERIVATIVE
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0677522A1

  公开（公告）日：1995-10-18

  An 8-methoxyquinolonecarboxylic acid derivative represented by general formula (I), and optical isomers, pharmaceutically acceptable salts and hydrates thereof, wherein R₁ represents hydrogen, lower alkyl, phenylalkyl or an in vivo hydrolyzable ester residue; R₂ represents hydrogen or methyl; and n represents an integer of 0 or 1. This derivative has a wide antimicrobial spectrum based on the activity potentiated in vitro and in vivo against gram-positive bacteria while retaining the potent antibacterial activity of the conventional quinolonecarboxylate bactericides against gram-negative bacteria. Since it scarcely has problematic side effects and is reduced in toxicity, it is promising as a bactericide having more excellent clinical effects.

  通式(I)代表的 8-甲氧基喹啉羧酸衍生物及其光学异构体、药学上可接受的盐和水合物，其中 R₁ 代表氢、低级烷基、苯基烷基或体内可水解的酯残基；R₂ 代表氢或甲基；n 代表 0 或 1 的整数。根据体外和体内对革兰氏阳性菌的增效活性，这种衍生物具有广泛的抗菌谱，同时保留了传统喹啉羧酸盐杀菌剂对革兰氏阴性菌的强效抗菌活性。由于它几乎没有副作用，毒性也较低，因此有望成为一种临床效果更佳的杀菌剂。
• CIS-SUBSTITUTED FLUOROMETHYLPYRROLIDINE DERIVATIVES
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP0995744A1

  公开（公告）日：2000-04-26

  An antibacterial drug having potent antibacterial activities upon various bacteria including resistant strains and high safety is disclosed, which comprises as an active ingredient, quinolone derivatives represented by the following formula (I), its salts or hydrates thereof: wherein R1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R2 represents a halogenomethoxyl group or an alkoxyl group, R3 represents an alkyl group, an alkenyl group, a halogenoalkyl group, a cyclic alkyl group, a heteroaryl group, an alkoxyl group or an alkylamino group, and R4 represents a hydrogen atom, a phenyl group, an acetoxymethyl group, a pivaloyloxymethyl group, an ethoxycarbonyl group, a choline group, a dimethylaminoethyl group, a 5-indanyl group, a phthalidinyl group, a 5-alkyl-2-oxo-1,3-dioxol-4-ylmethyl group, 3-acetoxy-2-oxobutyl group, an alkyl group, an alkoxylmethyl group or a phenylalkyl group. These substituents may further have additional substituents.

  本发明公开了一种对包括耐药菌株在内的各种细菌具有强效抗菌活性且安全性高的抗菌药，其活性成分包括下式(I)代表的喹诺酮衍生物、其盐类或水合物： 其中 R1 代表氢原子或具有 1 至 6 个碳原子的烷基、 R2 代表卤代甲氧基或烷氧基、 R3 代表烷基、烯基、卤代烷基、环烷基、杂芳基、烷氧基或烷基氨基，以及 R4 代表氢原子、苯基、乙酰氧甲基、新戊酰氧甲基、乙氧基羰基、胆碱基、二甲基氨基乙基、5-茚满基、酞丁基、5-烷基-2-氧代-1,3-二氧戊环-4-基甲基、3-乙酰氧基-2-氧代丁基、烷基、烷氧基甲基或苯基烷基。这些取代基可进一步具有其他取代基。
• Method for producing 8-methoxy-quinoline carboxylic acids
  申请人：Bayer Aktiengesellschaft

  公开号：US20030208069A1

  公开（公告）日：2003-11-06

  The present invention relates to a novel process for preparing 8-methoxy-3-quinolonecarboxylic acids which are antibiotics having potent antibacterial action.

  本发明涉及一种制备 8-甲氧基-3-喹啉羧酸的新工艺，这种抗生素具有很强的抗菌作用。