1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-3-quinoline-carboxylic acid | 130579-27-0

• 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-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-3-quinoline-carboxylic acid
• 英文别名: 1-cyclopropyl-1,4-dihydro-6-fluoro-7-hydroxy-4-oxo-quinoline-3-carboxylic acid；3-Quinolinecarboxylic acid,1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-；1-cyclopropyl-6-fluoro-7-hydroxy-4-oxoquinoline-3-carboxylic acid
• CAS: 130579-27-0
• 化学式: C₁₃H₁₀FNO₄
• 分子量: 263.225
• InChiKey: GLPHFHRWJZECNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  495.7±45.0 °C(Predicted)
• 密度：
  1.677±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-3-quinoline-carboxylic acid 在 吡啶 作用下， 生成 Benzyl-1-cyclopropyl-6-fluoro-4-oxo-7-{[(trifluoromethyl)sulfonyl]oxy}-1,4-dihydro-3-quinolinecarboxylate
  参考文献：
  名称：

  Novel oxazolidinone–quinolone hybrid antimicrobials

  摘要：

  Antimicrobial compounds incorporating oxazolidinone and quinolone pharmacophore substructures have been synthesized and evaluated. Representative analogues 2, 5, and 6 display an improved potency versus linezolid against gram-positive and fastidious gram-negative pathogens. The compounds are also active against linezolid- and ciprofloxacin-resistant Staphylococcus aureus and Enterococcus faecium strains. The MOA for these new antimicrobials is consistent with a combination of protein synthesis and gyrase A/topoisomerase IV inhibition, with a structure-dependent degree of the contribution from each inhibitory mechanism. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.021
• 作为产物：
  描述：

  1-环丙基-6,7-二氟-4-氧代-1,4-二氢喹啉-3-羧酸乙酯 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 8.0h， 生成 1-cyclopropyl-6-fluoro-1,4-dihydro-7-hydroxy-4-oxo-3-quinoline-carboxylic acid
  参考文献：
  名称：

  QUINOLONE DERIVATIVES USEFUL AS ANTIBACTERIAL AGENTS

  摘要：

  本发明涉及喹诺酮衍生物，作为抗微生物化合物有用，包括所述衍生物的药物组合物以及所述衍生物和药物组合物作为抗病原微生物的抗微生物剂的用途，特别是对抗耐药微生物。

  公开号：

  US20090270379A1

文献信息

• Antimicrobial quinolone derivatives and use of the same to treat bacterial infections
  申请人：——

  公开号：US20030013737A1

  公开（公告）日：2003-01-16

  Substituted quinolone derivatives in which an oxazolidinone, isoxazolinone, or isoxazoline is covalently bonded to a quinolone, methods of using the quinolone derivatives, and pharmaceutical compositions containing the quinolone derivatives are disclosed. Methods of synthesizing these substituted quinolone derivatives are also disclosed, and in particular a method of manufacturing a 7-(2-oxo-1,3-oxazolidin-3-yl)aryl-3-quinolinecarboxylic acid by condensing a 4-(2-oxo-1,3-oxazolidin-5-yl)aryl boronic acid with a 7-halo-quinolone derivative. The quinolone derivatives possess antibacterial activity, and are effective against a number of human and veterinary pathogens in the treatment of bacterial diseases.

  揭示了一种将氧唑烷烷酮、异唑啉烷酮或异唑啉与喹诺酮共价结合的取代喹诺酮衍生物，以及使用这些喹诺酮衍生物的方法和含有这些喹诺酮衍生物的药物组合物。还公开了合成这些取代喹诺酮衍生物的方法，特别是通过将4-(2-氧唑烷-5-基)芳基硼酸与7-卤代喹诺酮衍生物缩合制备7-(2-氧唑烷-1,3-二烷基)芳基-3-喹诺酸的方法。这些喹诺酮衍生物具有抗菌活性，对治疗细菌疾病中的多种人类和兽医病原体有效。
• Synthesis of 7-(alkenyl, cycloalkenyl, and 1,2,3,6-tetrahydro-4-pyridinyl)quinolones
  作者：John S. Kiely、Edgardo Laborde、Lawrence E. Lesheski、Ruth A. Bucsh

  DOI：10.1002/jhet.5570280621

  日期：1991.10

  in which the C-7 position is substituted with a vinyl, a 1-cyclopentenyl, or a 1,2,3,6-tetrahydro-4-pyridinyl group. These quinolones were synthesized via a palladium-catalyzed cross coupling of a 7-quinolyltriflate with an appropriately functionalized vinylstannane.

  制备了一系列的1-环丙基-1,4-二氢-4-氧代喹啉，其中C-7位置被乙烯基，1-环戊烯基或1,2,3,6-四氢-4-取代吡啶基。这些喹诺酮是通过钯催化的7-喹啉滤液与适当官能化的乙烯基锡烷的交叉偶联而合成的。
• On-Demand Continuous Manufacturing of Ciprofloxacin in Portable Plug-and-Play Factories: Development of a Highly Efficient Synthesis for Ciprofloxacin
  作者：Cameron Armstrong、Yuma Miyai、Anna Formosa、Dale Thomas、Esther Chen、Travis Hart、Victor Schultz、Bimbisar K. Desai、Angela Y. Cai、Alexandra Almasy、Klavs Jensen、Luke Rogers、Tom Roper

  DOI：10.1021/acs.oprd.1c00118

  日期：2021.7.16
• KIELY, JOHN S.;LESHESKI, LAWRENCE E.;SCHROEDER, MEL. C.
  作者：KIELY, JOHN S.、LESHESKI, LAWRENCE E.、SCHROEDER, MEL. C.

  DOI：——

  日期：——
• ANTIMICROBIAL QUINOLONE DERIVATIVES AND USE OF THE SAME TO TREAT BACTERIAL INFECTIONS
  申请人：Pharmacia & Upjohn Company LLC

  公开号：EP1349853B1

  公开（公告）日：2006-03-08