AMQ4 | 103460-90-8

• 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: AMQ4
• 英文别名: sparfloxacin；3-Quinolinecarboxylic acid, 1-cyclopropyl-7-(3,5-dimethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-；1-cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 103460-90-8
• 化学式: C₁₉H₂₁F₂N₃O₃
• 分子量: 377.391
• InChiKey: CMGSYIRPKZAEFD-UHFFFAOYSA-N

物化性质

• 熔点：
  232-240.25 °C
• 沸点：
  565.8±50.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  二氯(1,10-菲咯啉)铜(II) 、 AMQ4 以 甲醇 为溶剂， 以72%的产率得到[CuCl2(1,10-phenanhroline)(sparfloxacin)]*3H2O
  参考文献：
  名称：

  Co(II), Mn(II) and Cu(II) complexes of fluoroquinolones: Synthesis, spectroscopical studies and biological evaluation against Trypanosoma cruzi

  摘要：

  [MnCl2(NOR)(H2O)(2)] (1), [MnCl2(SPAR)(H2O)(2)] (2), [CoCl2(NOR)(H2O)(2)] (3) [CoCl2(SPAR)(H2O)(2)] (4), [CuCl2(phen)(NOR)] (5) and [CuCl2(phen)(SPAR)] (6) complexes with norfloxacin (NOR) and sparfloxacin (SPAR) were obtained from MnCl2 center dot 4H(2)O, CoCl2 center dot 4H(2)O and CuCl2(phen). In all cases the NOR and SPAR coordinate in the neutral zwitterionic form. The electron paramagnetic resonance spectra of the Cu(II) complexes (5) and (6) in aqueous and DMSO solutions indicate mixture of mononuclear and binuclear complex. Complexes (1-6), together with the corresponding ligands were evaluated for their in vitro trypanocidal effect, against both bloodstream trypomastigotes and intracellular forms of Trypanosoma SPAR and NOR were poorly effective upon T. cruzi, complexes (3) and (4) were active against intracellular forms of the parasite. The complexes (5) and (6) displayed a higher activity upon both bloodstream and intracellular forms. The potency of fluoroquinolones, specially those coordinated to Cu(II)-phen justify further trypanocidal screening assays with this compounds in vitro as well as upon experimental models of T. cruzi infection. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.04.001
• 作为产物：
  描述：

  3-Quinolinecarboxylic acid, 1-cyclopropyl-7-(3,5-diMethyl-1-piperazinyl)-6,8-difluoro-1,4-dihydro-4-oxo-, ethyl ester 生成 AMQ4
  参考文献：
  名称：

  IRIKURA, TSUTOMU;SUDZUEH, SEHJGO;XIRAI, KEHJDZI;ISIDZAKI, TAKAESI

  摘要：

  DOI：

文献信息

• Quinolinecarboxylic acid derivatives
  申请人：KYORIN PHARMACEUTICAL CO., LTD.

  公开号：EP0178388A1

  公开（公告）日：1986-04-23

  57 Quinolonecarboxylic acid derivatives of the following formula, wherein R' is hydrogen atom or lower alkyl group, R2 is hydrogen atom or methyl group and Y is chlorine or fluorine atom, the hydrates and pharmaceutically acceptable salts thereof, are useful as an antibacterial agent.

  57 下式的喹啉羧酸衍生物、 其中 R' 为氢原子或低级烷基，R2 为氢原子或甲基，Y 为氯原子或氟原子，其水合物和药学上可接受的盐类可用作抗菌剂。
• Novel quinoline derivatives, processes for preparation thereof and antibacterial agent containing them
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0319906A2

  公开（公告）日：1989-06-14

  1-Substituted-6-fluoro-5-methyl-7-(piperazinyl or pyrrolidinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acids (I) and processes for preparation thereof. The acids are used for treatment of a bacterial infectious desease.

  1-取代-6-氟-5-甲基-7-(哌嗪基或吡咯烷基)-1,4-二氢-4-氧代喹啉-3-羧酸 (I) 及其制备方法。这些酸可用于治疗细菌性传染病。
• Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship
  作者：John M. Domagala、Alex J. Bridges、Townley P. Culbertson、Laura Gambino、Susan E. Hagen、Gregory Karrick、Kenneth Porter、Joseph P. Sanchez、Josephine A. Sesnie

  DOI：10.1021/jm00107a039

  日期：1991.3

  A series of 5-amino- and 5-hydroxyquinolone antibacterials substituted at C7 with a select group of common piperazinyl and 3-aminopyrrolidinyl side chains was prepared. These 5-substituted derivatives were compared to the analogous 5-hydrogen compounds for antiinfective activity by using DNA gyrase inhibition, minimum inhibitory concentrations against a variety of bacteria, and in vivo efficacy in the mouse infection model. The influence on the structure-activity relationships of varied substituents at C8 (H, F, Cl) and Ni (ethyl, cyclopropyl, difluorophenyl) was also studied. The results showed that several of the structure-activity conclusions regarding side-chain bulk at C7, the effect of halogen at C8, and the effect of the C5-amino group were greatly influenced by the choice of the N1-substituent. Several outstanding broad spectrum quinolones were identified in this work. In particular, the spectrum and potency of the 7-piperazinyl quinolones could be greatly enhanced by the judicious choice of C5-, C8-, and N1-substitutents.
• DOMAGALA, JOHN M.;BRIDGES, ALEX J.;CULBERTSON, TOWNLEY P.;GAMBINO, LAURA;+, J. MED. CHEM., 34,(1991) N, C. 1142-1154
  作者：DOMAGALA, JOHN M.、BRIDGES, ALEX J.、CULBERTSON, TOWNLEY P.、GAMBINO, LAURA、+

  DOI：——

  日期：——
• IRIKURA, TSUTOMU;SUDZUEH, SEHJGO;XIRAI, KEHJDZI;ISIDZAKI, TAKAESI
  作者：IRIKURA, TSUTOMU、SUDZUEH, SEHJGO、XIRAI, KEHJDZI、ISIDZAKI, TAKAESI

  DOI：——

  日期：——