(+/-)-5-amino-1-cyclopropyl-6,8-difluoro-7-(2-methyl-1-piperazinyl)-4(1H)-oxoquinoline-3-carboxylic acid | 110871-95-9

• 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: (+/-)-5-amino-1-cyclopropyl-6,8-difluoro-7-(2-methyl-1-piperazinyl)-4(1H)-oxoquinoline-3-carboxylic acid
• 英文别名: 5-Amino-1-cyclopropyl-6,8-difluoro-7-(2-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• CAS: 110871-95-9
• 化学式: C₁₈H₂₀F₂N₄O₃
• 分子量: 378.379
• InChiKey: MJWDASPKPSXBRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  98.9
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-氨基-1-环丙基-6,7,8-三氟-4-氧代-1,4-二氢-3-喹啉羧酸 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.67h， 生成 (+/-)-5-amino-1-cyclopropyl-6,8-difluoro-7-(2-methyl-1-piperazinyl)-4(1H)-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Pyridonecarboxylic acids as antibacterial agents. Part 14. Synthesis and structure-activity relationships of 5-substituted 6,8-difluoroquinolones, including sparfloxacin, a new quinolone antibacterial agent with improved potency

  摘要：

  A series of 5,7-disubstituted 1-cyclopropyl-6,8-difluoro-4(1H)-oxoquinoline-3-carboxylic acids (10-36) were prepared; the C-5 substituent in these compounds comprised halo, hydroxy, mercapto, and amino groups and the C-7 functional group included variously substituted piperazines. In vitro antibacterial screening results indicated that the amino group was optimal among the C-5 substituents. A combination of the C-5 amino group and the C-7 3,5-dimethylpiperazinyl appendage in this series conferred the best overall antibacterial property with lack of adverse drug interactions. Compound 36k [named sparfloxacin, originally AT-4140, 5-amino-1-cyclopropyl-6,8-difluoro-7-(cis-3,5-dimethyl-1-piperazinyl)- 4(1H)-oxoquinoline-3-carboxylic acid] was superior to ciprofloxacin in both in vitro and in vivo potency and hence was selected as a promising candidate for an improved therapeutic agent.

  DOI：

  10.1021/jm00168a018

文献信息

• Quinoline derivatives and processes for preparation thereof
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0221463A2

  公开（公告）日：1987-05-13

  The present invention relates to a quinoline derivative of the formula wherein Z is an amino group or a halogen atom, R, is a hydrogen atom or a methyl or ethyl group, R2 is a hydrogen atom or a methyl or fluoromethyl group, R3 and R4 are the same or different and each represents a hydrogen atom or a methyl group, and n is 1 or 2; and esters thereof and salts thereof and processes for preparation thereof. These compounds show excellent antibacterial activity and are useful antibacterial agents.

  本发明涉及一种式如下的喹啉衍生物 其中 Z 是氨基或卤原子，R, 是氢原子或甲基或乙基，R2 是氢原子或甲基或氟甲基，R3 和 R4 相同或不同且各自代表氢原子或甲基，n 是 1 或 2； 及其酯类、盐类和制备工艺。这些化合物显示出卓越的抗菌活性，是有用的抗菌剂。
• MIYAMOTO, TERUYUKI;MATSUMOTO, JUN-ICHI;CHIBA, KATSUMI;EGAWA, HIROSHI;SHIB+, J. MED. CNEM., 33,(1990) N, C. 1645-1656
  作者：MIYAMOTO, TERUYUKI、MATSUMOTO, JUN-ICHI、CHIBA, KATSUMI、EGAWA, HIROSHI、SHIB+

  DOI：——

  日期：——
• US4795751A
  申请人：——

  公开号：US4795751A

  公开（公告）日：1989-01-03
• Pyridonecarboxylic acids as antibacterial agents. Part 14. Synthesis and structure-activity relationships of 5-substituted 6,8-difluoroquinolones, including sparfloxacin, a new quinolone antibacterial agent with improved potency
  作者：Teruyuki Miyamoto、Junichi Matsumoto、Katsumi Chiba、Hiroshi Egawa、Kohichiro Shibamori、Akira Minamida、Yoshiro Nishimura、Hidetsugu Okada、Masahiro Kataoka

  DOI：10.1021/jm00168a018

  日期：1990.6

  A series of 5,7-disubstituted 1-cyclopropyl-6,8-difluoro-4(1H)-oxoquinoline-3-carboxylic acids (10-36) were prepared; the C-5 substituent in these compounds comprised halo, hydroxy, mercapto, and amino groups and the C-7 functional group included variously substituted piperazines. In vitro antibacterial screening results indicated that the amino group was optimal among the C-5 substituents. A combination of the C-5 amino group and the C-7 3,5-dimethylpiperazinyl appendage in this series conferred the best overall antibacterial property with lack of adverse drug interactions. Compound 36k [named sparfloxacin, originally AT-4140, 5-amino-1-cyclopropyl-6,8-difluoro-7-(cis-3,5-dimethyl-1-piperazinyl)- 4(1H)-oxoquinoline-3-carboxylic acid] was superior to ciprofloxacin in both in vitro and in vivo potency and hence was selected as a promising candidate for an improved therapeutic agent.