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8-Chloro-1-(2,4-difluoro-phenyl)-6,7-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid | 112282-65-2

中文名称
——
中文别名
——
英文名称
8-Chloro-1-(2,4-difluoro-phenyl)-6,7-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
英文别名
8-Chloro-1-(2,4-difluorophenyl)-6,7-difluoro-4-oxoquinoline-3-carboxylic acid
8-Chloro-1-(2,4-difluoro-phenyl)-6,7-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid化学式
CAS
112282-65-2
化学式
C16H6ClF4NO3
mdl
——
分子量
371.675
InChiKey
JUGFXFSMHPECQE-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4.6
  • 重原子数:
    25
  • 可旋转键数:
    2
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.0
  • 拓扑面积:
    57.6
  • 氢给体数:
    1
  • 氢受体数:
    8

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    8-Chloro-1-(2,4-difluoro-phenyl)-6,7-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid吡啶sodium hydroxide三乙胺 作用下, 反应 5.0h, 生成 8-Chloro-1-(2,4-difluoro-phenyl)-6-fluoro-7-(3-methylamino-azetidin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
    参考文献:
    名称:
    7-Azetidinylquinolones as antibacterial agents. Synthesis and structure-activity relationships
    摘要:
    A series of novel antibacterial quinolones and naphthyridones has been prepared which contain 7-azetidinyl substituents in place of the usual piperazine or aminopyrrolidine groups. These azetidinyl derivatives were evaluated for in vitro activity by determining minimum inhibitory concentrations against a variety of bacteria. In vivo efficacy in the mouse infection model and blood levels in the mouse were determined for several compounds. The influence on the structure-activity relationships of varying substituents in the azetidine ring and at position 8 (CH, CF, CCl, N) and N-1 (ethyl, fluoroethyl, cyclopropyl, tert-butyl, 4-fluorophenyl, and 2,4-difluorophenyl) was also studied. Compounds with outstandingly broad-spectrum activity, particularly against Gram-positive organisms, improved in vivo efficacy, and high blood levels were identified in this work. 7-Azetidinyl-8-chloroquinolones were considered as warranting further development.
    DOI:
    10.1021/jm00059a002
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文献信息

  • Synthesis and structure-activity relationships of 7-diazabicycloalkylquinolones, including danofloxacin, a new quinolone antibacterial agent for veterinary medicine
    作者:Paul R. McGuirk、Martin R. Jefson、Douglas D. Mann、Nancy C. Elliott、Polly Chang、Eugene P. Cisek、C. Peter Cornell、Thomas D. Gootz、Susan L. Haskell
    DOI:10.1021/jm00082a001
    日期:1992.2
    diazabicycloalkyl side chains investigated at the 7-position (benzoxazine 10-position) include (1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptane (2), (1S,4S)-2,5-diazabicyclo[2.2.1]heptane (3), (1R,4R)-5-methyl-2,5-diazabicyclo[2.2.1]heptane (4), 8-methyl-3,8-diazabicyclo[3.2.1]octane (5), 9-methyl-3,9-diazabicyclo[4.2.1]nonane (6), 1,4-diazabicyclo[3.2.2]nonane (7), 1,4-diazabicyclo[3.3.1]nonane (8), and 9-methyl-3
    一系列被各种C8(H,F,Cl,N)和N1(乙基,环丙基,乙烯基,2-氟乙基,4-氟苯基,2,4-二氟苯基)取代基取代的新颖的6-氟-7-二氮杂双环烷基喹诺酮羧酸,以及9-氟-10-二氮杂双环烷基吡啶并苯并恶嗪羧酸,并针对一系列重要的兽医病原菌进行了抗菌活性评估。在7位(苯并恶嗪10位)研究的二氮杂双环烷基侧链包括(1S,4S)-5-甲基-2,5-二氮杂双环[2.2.1]庚烷(2),(1S,4S)-2, 5-二氮杂双环[2.2.1]庚烷(3),(1R,4R)-5-甲基-2,5-二氮杂双环[2.2.1]庚烷(4),8-甲基-3,8-二氮杂双环[3.2。 1]辛烷(5),9-甲基-3,9-二氮杂双环[4.2.1]壬烷(6),1,4-二氮杂双环[3.2.2]壬烷(7),1,4-二氮杂双环[3.3.1] ]壬烷(8)和9-甲基-3,9-二氮杂双环[3.3.1]壬烷(9)。在这些侧链中,体外效能不是
  • 7-Azetidinylquinolones as Antibacterial Agents. 2. Synthesis and Biological Activity of 7-(2,3-Disubstituted-1-azetidinyl)-4-oxoquinoline- and -1,8-naphthyridine-3-carboxylic Acids. Properties and Structure-Activity Relationships of Quinolones with an Azetidine Moiety
    作者:Jordi Frigola、Antoni Torrens、Jose A. Castrillo、Josep Mas、David Vano、Juana M. Berrocal、Carme Calvet、Leonardo Salgado、Jordi Redondo
    DOI:10.1021/jm00050a016
    日期:1994.11
    3-disubstituted-1-azetidinyl)-1,4-dihydro-6-fluoro-4- oxoquinoline- and -1,8-naphthyridine-3-carboxylic acids, with varied substituents at the 1-, 5-, and 8-positions, was prepared to study the effects on potency and physicochemical properties of the substituent at position 2 of the azetidine moiety. The activity of the title compounds was determined in vitro against Gram-positive and Gram-negative bacteria
    一系列7-(2,3-二取代-1-氮杂环丁烷基)-1,4-二氢-6-氟-4-氧代喹啉-和-1,8-萘啶-3-羧酸,在1处具有不同的取代基制备5-,5-和8-位,以研究对氮杂环丁烷部分2位上的取代基的效能和理化性质的影响。在体外确定针对革兰氏阳性和革兰氏阴性细菌的标题化合物的活性,并使用小鼠感染模型确定所选衍生物的体内功效。发现6b,6c和6d的X射线晶体结构与相应的AM1计算的几何结构合理吻合。建立了所有合成的7-氮杂环丁烷基喹诺酮类和萘啶类的抗菌能力与计算出的电子性质和实验容量因子之间的相关性。将所选衍生物的抗菌功效,药代动力学和理化性质与相关的7-(3-氨基-1-氮杂环丁烷基)和7-(3-氨基-3-甲基-1-氮杂环丁烷基)类似物进行了比较(第1部分,请参见: J. Med。Chem。1993,36,801-810)。N-1处的环丙基或取代的苯基与C-7处的反-3-氨基-2-甲基-1-氮杂
  • 7-Azetidinylquinolones as Antibacterial Agents. 3. Synthesis, Properties and Structure-Activity Relationships of the Stereoisomers Containing a 7-(3-Amino-2-methyl-1-azetidinyl) Moiety
    作者:Jordi Frigola、David Vano、Antoni Torrens、Angels Gomez-Gomar、Edmundo Ortega、Santiago Garcia-Granda
    DOI:10.1021/jm00007a017
    日期:1995.3
    de]-1,4-benzoxazine-6-carboxylic acids was synthesized to study the effect of the azetidine moiety on tricyclic quinolone antibacterial agents. A series of amino acid prodrugs of chiral naphthyridines 24a and 24b and quinolone 33a (cetefloxacin) was prepared and evaluated for antibacterial activity, solubility, and pharmacokinetic behavior. The absolute configuration of the new azetidinylquinolones
    一系列立体化学纯的7-(3-氨基-2-甲基-1-氮杂环丁烷基)-1,4-二氢-6-氟-4-氧代喹啉-和-1,8-萘啶-3-羧酸制备了位于1、5和8位的取代基,以确定手性相对于外消旋混合物的效价和体内功效的影响(第2部分,参见:J. Med.Chem。1994,37, 4195-4210)。一系列手性9-氟-2,3-二氢-3-甲基-7-氧-10-(取代的1-氮杂环丁烷基)-7H-吡啶[1,2,3-de] -1,4-苯并恶嗪合成-6-羧酸以研究氮杂环丁烷部分对三环喹诺酮抗菌剂的作用。制备了一系列手性萘啶24a和24b以及喹诺酮33a(cetefloxacin)的氨基酸前药,并评估了其抗菌活性,溶解度和药代动力学行为。通过对拆分的氮杂环丁醇(15)和化合物25a(E-4767)的一种非对映异构盐进行X射线分析,可以确定新的氮杂环丁烷基喹诺酮类化合物的绝对构型,该化合物在体外和体内的总体情况最佳。
  • 8-Position substituted quinolone-carboxylic acid derivatives and process for their preparation
    申请人:KYORIN PHARMACEUTICAL CO., LTD.
    公开号:EP0235762A1
    公开(公告)日:1987-09-09
    The present invention is concerned with certain novel quinolonecarboxylic acid derivatives of the following formula, wherein R indicates chlorine, bromine, nitro, cyano,-OR2,-SR2 or -NR2R3 (here, R2 and R3 indicate hydrogen or lower alkyl each independently), R1 indicates ethyl, 4-fluorophenyl or 2,4-di-fluorophenyl, Z indicates a piperazino group of the following formula, (here, R4 indicates hydrogen, methyl or lower alkoxycarbonyl, R5 indicates hydrogen or lower alkyl) or a pyrrolidine group of the following formula, (here, n is 0 or 1, R6 indicates hydrogen or methyl, R7 indicates hydrogen atom or lower alkyl group, R8 indicates a hydrogen, lower alkyl, lower acyl or lower alkoxycarbonyl), with the proviso that when R1 is ethyl and R is chlorine, Z is not piperazino or 4-methylpiperazino; the hydrates and pharmaceutically acceptable salts thereof are useful as an antibacterial agent.
    本发明涉及下式的某些新型喹啉羧酸衍生物、 其中 R 表示氯、溴、硝基、氰基、-OR2、-SR2 或 -NR2R3 (此处 R2 和 R3 分别独立地表示氢或低级烷基),R1 表示乙基、4-氟苯基或 2,4-二氟苯基,Z 表示下式的哌嗪基团、 (此处,R4 表示氢、甲基或低级烷氧基羰基,R5 表示氢或低级烷基)或下式的吡咯烷基团、 (此处,n 为 0 或 1,R6 表示氢或甲基,R7 表示氢原子或低级烷基,R8 表示氢、低级烷基、低级酰基或低级烷氧羰基),但当 R1 为乙基、R 为氯时,Z 不是哌嗪基或 4-甲基哌嗪基;其水合物和药学上可接受的盐可用作抗菌剂。
  • Chinoloncarbonsäurederivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als antivirale Mittel
    申请人:BAYER AG
    公开号:EP0422485A2
    公开(公告)日:1991-04-17
    Die Erfindung betrifft neue Chinoloncarbonsäurederivate der allgemeinen Formel (I) in der R, R1, R2, R3, R5 und A die in der Beschreibung angegebene Bedeutung haben, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel, insbesondere als antivirale Mittel.
    本发明涉及通式(I)的新喹啉羧酸衍生物。 中 R、R1、R2、R3、R5 和 A 的含义,以及它们的制备工艺和作为药物,特别是作为抗病毒药物的用途。
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