ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylate | 125290-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylate
• 英文别名: 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester；ethyl 7-chloro-1-cyclopropyl-1,4-dihydro-6-fluoro-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylate；Ethyl 7-chloro-1-cyclopropyl-6-fluoro-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylate
• CAS: 125290-83-7
• 化学式: C₁₅H₁₄ClFN₂O₃
• 分子量: 324.739
• InChiKey: ZCMDRXDZZYUFFN-UHFFFAOYSA-N

物化性质

• 沸点：
  494.7±45.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylate 在 palladium on activated charcoal 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 生成 1-Cyclopropyl-6-fluoro-5-methyl-7-((1R,4R,6R)-6-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  氟萘啶类用作抗菌剂。6. 7-[[]的新手性7-（1-，3-，4-和6-甲基-2,5-二氮杂双环[2.2.1]庚-2-基）萘啶类似物的合成及构效关系（1R，4R）-2，5-二氮杂双环[2.2.1]庚-2-基] -1-（1，1-二甲基乙基）-6-氟-1，4-二氢dro-4-oxo-1， 8-萘啶-3-羧酸。构型对狗血压的影响。喹诺酮类效果。

  摘要：

  8-萘啶-3-羧酸（49）对革兰氏阳性和革兰氏阴性细菌表现出强大的体外和体内抗菌活性。与狗1a静脉输注后相比，衍生物49与1a相比，血压（MAP）下降幅度较小，并被选作临床前试验的潜在候选者。

  DOI：

  10.1021/jm00093a024
• 作为产物：
  描述：

  2,6-二氯-5-氟烟酸 在 五氯化磷 、 甲基锂 、 乙酸酐 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 25.63h， 生成 ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylate
  参考文献：
  名称：

  Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted 6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids

  摘要：

  A series of 5-substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids have been prepared and tested for their in vitro and in vivo antibacterial activities. The 5-methyl group gave better in vitro activity with the 1-cyclopropyl appendage, but poorer activity with the 1-tert-butyl moiety. With the 1-(2,4-difluorophenyl) substitution, the influence of the 7-cycloalkylamino group was determinant: a (3S)-3-amino-pyrrolidine was shown to enhance greatly the in vitro and in vivo activity of the 5-methyl derivative. Compound 33 (BMY 43748) was selected as a promising candidate for an improved therapeutic agent.

  DOI：

  10.1021/jm00081a013

文献信息

• Antibacterial agents
  申请人：Warner-Lambert Company

  公开号：US04920120A1

  公开（公告）日：1990-04-24

  Novel naphthyridine-, and quinolinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

  描述了新型萘啶基和喹啉基羧酸作为抗菌剂的小说，以及它们的制造、配方和用于治疗细菌感染的方法，包括用于制造抗菌剂的某些新型中间体的描述。
• Quinoline and naphthyridine carboxylic acid antibacterials
  申请人：——

  公开号：US20020049223A1

  公开（公告）日：2002-04-25

  Compounds having formula (I) 1 or pharmaceutically acceptable salts or prodrugs thereof, are useful as antibacterial agents.

  具有化学式(I)1的化合物或其药用可接受的盐或前药，可用作抗菌剂。
• 5-Substituted-1,4-dihydro-4-oxonaphthyridine-3-carboxylate antibacterial agents
  申请人：Bristol-Myers Squibb Company

  公开号：EP0387802A3

  公开（公告）日：1991-09-25

  The invention is concerned with naphthyridine compounds of formula (I) which are substituted in the 7-position with various nitrogen heterocyclo groups and at the 1,3,4,5 and 6-positions with certain other groups. These compounds are antibacterial agents and are suitable for the treatment of infections.

  该发明涉及公式（I）中在7位取代各种氮杂环基团，在1,3,4,5和6位取代特定其他基团的萘啶化合物。这些化合物是抗菌剂，适用于治疗感染。
• The preparation of ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylate
  作者：John S. Kiely

  DOI：10.1002/jhet.5570280265

  日期：1991.2

  Ethyl 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid has been prepared by a route involving masking of the C2,3 double bond through reduction, followed by regioselective deprotonation of the C5 position and methylation and then regeneration of the C2,3 double bond via selenation, oxidation, and syn-elimination.

  乙基7-氯-1-环丙基-6-氟-1,4-二氢-5-甲基-4-氧代-1,8-萘啶-3-羧酸已通过涉及C 2的掩蔽的方法制备通过还原形成3个双键，然后通过C 5位置的区域选择性去质子化和甲基化，然后通过硒化，氧化和同消去再生C 2,3双键。
• Naphthyridone carboxylic acid derivatives and antibacterial compositions containing them
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0544981A2

  公开（公告）日：1993-06-09

  The application comprises new compounds of the formula IV wherein R₂ is cyclopropyl or 2,4-difluorophenyl and Z is a group wherein R₅ and R₆ are each independently hydrogen and alkyl with 1 to 4 carbon atoms and n is an integer of from 0 to 4, a process of manufacture and pharmaceutical compositions useful as antibacterials.

  本申请包括式 IV 的新化合物 其中 R₂ 是环丙基或 2,4-二氟苯基，Z 是一个基团 其中R₅和R₆各自独立地为氢和含有1至4个碳原子的烷基，n为0至4的整数，该化合物的制造工艺和用作抗菌剂的药物组合物。