(+/-)-1-cyclopropyl-5,6,8-trifluoro-7-(3-methyl-1-piperazinyl)-4(1H)-oxoquinoline-3-carboxylic acid | 110871-96-0

• 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
• 英文名称: (+/-)-1-cyclopropyl-5,6,8-trifluoro-7-(3-methyl-1-piperazinyl)-4(1H)-oxoquinoline-3-carboxylic acid
• 英文别名: 1-cyclopropyl-5,6,8-trifluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid；1-Cyclopropyl-5,6,8-trifluoro-7-(3-methyl 1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid；1-cyclopropyl-5,6,8-trifluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• CAS: 110871-96-0
• 化学式: C₁₈H₁₈F₃N₃O₃
• 分子量: 381.354
• InChiKey: UVPAOMFBMNZWTA-UHFFFAOYSA-N

物化性质

• 熔点：
  235-237 °C
• 沸点：
  593.3±50.0 °C(Predicted)
• 密度：
  1.494±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 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：
  72.9
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (+/-)-1-cyclopropyl-5,6,8-trifluoro-7-(3-methyl-1-piperazinyl)-4(1H)-oxoquinoline-3-carboxylic acid 在 ammonium hydroxide 作用下， 以 水 为溶剂， 生成 5-amino-1-cyclopropyl-6,8-difluoro-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Quinoline derivatives and processes for preparation thereof

  摘要：

  公开号：

  EP0221463B1
• 作为产物：
  描述：

  difluoroboranyl 1-cyclopropyl-5,6,8-trifluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylate 生成 (+/-)-1-cyclopropyl-5,6,8-trifluoro-7-(3-methyl-1-piperazinyl)-4(1H)-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  HAKAHO, DZYUNDZI;NISIMURA, JOSIRO;MIYAMOTO, KOYUKI;MATSUMOTO, DZYUNITI

  摘要：

  DOI：

文献信息

• 5-Substituierte Chinolon- und Naphthyridoncarbonsäure-Derivate
  申请人：BAYER AG

  公开号：EP0284935A1

  公开（公告）日：1988-10-05

  Die Erfindung betrifft 5-substituierte Chinolon-und Naphthyridoncarbonsäure-Derivate der Formel (I) in welcher X, Y, R', R2 und R3 die in der Beschreibung angegebene Bedeutung haben. Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel und Futterzusatzstoffe.

  本发明涉及式(I)的5-取代喹诺酮和萘啶酮羧酸衍生物，其中X，Y，R'，R2和R3具有描述中所述的含义。制备它们的方法以及包含它们的抗菌剂和饲料添加剂。
• 5-substituted-6,8-difluoroquinolines useful as antibacterial agents
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US04795751A1

  公开（公告）日：1989-01-03

  The present invention relates to a quinoline derivative of the formula ##STR1## wherein Z is an amino group or a halogen atom, R.sub.1 is a hydrogen atom or a methyl or ethyl group, R.sub.2 is a hydrogen atom or a methyl or fluoromethyl group, R.sub.3 and R.sub.4 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.

  本发明涉及一种喹啉衍生物，其化学式为##STR1## 其中Z是氨基或卤素原子，R.sub.1是氢原子或甲基或乙基基团，R.sub.2是氢原子或甲基或氟甲基基团，R.sub.3和R.sub.4相同或不同，分别表示氢原子或甲基基团，n为1或2;以及它们的酯和盐及其制备方法。这些化合物表现出优异的抗菌活性，是有用的抗菌剂。
• Quinoline derivatives, pharmaceutical composition and method of use
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US04886810A1

  公开（公告）日：1989-12-12

  The present invention relates to quinoline derivatives of the formula ##STR1## wherein Z is an amino group or a halogen atom, R is ##STR2## in which R.sub.1 is a hydrogen atom, a lower alkyl or haloalkyl group, R.sub.2 is a hydrogen atom or a lower alkyl group, R.sub.3 is a lower alkyl or haloalkyl group, R.sub.4 is a hydrogen atom or a lower alkyl group, R.sub.5 and R.sub.6 are the same or different and each represents a hydrogen atom or a lower alkyl group, or R.sub.5 and R.sub.6, together with the nitrogen atom to which they are attached, form a heterocyclic ring, and n is 0 or 1, with the proviso that when Z is an amino group, R is (B); and esters thereof and salts thereof and processes for preparation thereof. These compounds show excellent antibacterial activity and are useful antibacterial agents.

  本发明涉及式（I）的喹啉衍生物：其中Z是氨基或卤素原子，R是式（II）：其中R1是氢原子、低碳基或卤代低碳基，R2是氢原子或低碳基，R3是低碳基或卤代低碳基，R4是氢原子或低碳基，R5和R6相同或不同，分别代表氢原子或低碳基，或R5和R6与它们所连接的氮原子形成杂环环，n为0或1，但当Z是氨基时，R为（B）；以及它们的酯和盐以及其制备方法。这些化合物表现出优异的抗菌活性，是有用的抗菌剂。
• Novel quinoline derivates and processes for preparation thereof
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0242789A2

  公开（公告）日：1987-10-28

  The present invention relates to quinoline derivatives of the formula wherein Z is an amino group or a halogen atom, in which R1 is a hydrogen atom, a lower alkyl or haloalkyl group, R2 is a hydrogen atom or a lower alkyl group, R3 is a lower alkyl or haloalkyl group, R4 is a hydrogen atom or a lower alkyl group, R5 and R6 are the same or different and each represents a hydrogen atom or a lower alkyl group, or R5 and Rs, together with the nitrogen atom to which they are attached, form a heterocyclic ring, and n is 0 or 1, with the proviso that when Z is an amino group R is (B); and esters thereof and salts thereof and processes for preparation thereof. These compounds show excellent ant- bacterial activity and are useful antibacterial agents.

  本发明涉及式中 Z 为氨基或卤素原子的喹啉衍生物，其中 R1 为氢原子、低级烷基或卤代烷基，R2 为氢原子或低级烷基，R3 为低级烷基或卤代烷基，R4 为氢原子或低级烷基，R5 和 R6 相同或不同，且各自代表氢原子或低级烷基，或 R5 和 Rs 与它们所连接的氮原子一起形成杂环，且 n 为 0 或 1，但当 Z 为氨基时，R 为（B）；以及其酯和盐及其制备工艺。 这些化合物显示出优异的抗菌活性，是有用的抗菌剂。
• 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.