6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid potassium salt | 115699-47-3

• 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: 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid potassium salt
• 英文别名: 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylate potassium salt；Potassium;6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylate
• CAS: 115699-47-3
• 化学式: C₁₇H₁₇F₃N₃O₃*K
• 分子量: 407.434
• InChiKey: DCKIEHUEZQBPSD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.63
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid potassium salt 在 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-3-[[6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carbonyl]oxymethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Cephalosporin 3'-quinolone esters with a dual mode of action

  摘要：

  According to the generally accepted mechanism by which bacterial enzymes react with cephalosporins, opening of the beta-lactam ring can lead to the expulsion of a 3'-substituent. A series of dual-action cephalosporins was prepared in which antibacterial quinolones were linked to the cephalosporin 3'-position through an ester bond in the expectation that, in addition to exerting their own beta-lactam activity, these cephalosporins would act as prodrugs for the second antibacterial agent. Compared to parent cephalosporins in which the 3'-substituent was acetoxy, the bifunctional cephalosporins exhibited a broadened antibacterial spectrum, suggesting that a dual mode of action may indeed be operative.

  DOI：

  10.1021/jm00163a013

文献信息

• Carbapenem compounds
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0451764A1

  公开（公告）日：1991-10-16

  Carbapenem compounds of the general formula wherein R is hydrogen or a carboxylic acid protecting group; R1 is selected from the group consisting of hydrogen, lower alkyl, lower alkoxy and hydroxyalkyl; R2 and R3 are each independently hydrogen, lower alkyl, lower alkoxy or lower alkylthio; and Y is (i) an ester group; (ii) a thioester group; (iii) a piperazinyl or pyrrolidinyl derived carbamate group; (iv) a piperazinyl derived amine group; (v) a piperazinyl derived quaternary ammonium group; or (vi) a group comprising a covalent bond; the ester group and the thioester group being bonded to a substituted quinolonyl or naphthyridonyl group; the piperazinyl or pyrrolidinyl derived carbamate group, the piperazinyl derived amine group and the piperazinyl derived quaternary ammonium group containing a piperazinyl nucleus or a pyrrolidinyl nucleus having a nitrogen atom bonded directly to a substituted quinolonyl or naphthyridonyl group, the piperazinyl and the pyrrolidinyl nuclei being unsubstituted or substituted with one or more lower alkyl groups; and the covalent bond of the corresponding group being connected to a substituted isothiazolo or isoxazolo quinolonyl or naphthyridonyl group via a nitrogen atom in an isothiazolo or isoxazolo nucleus; as well as the corresponding readily hydrolyzable esters, pharmaceutically acceptable salts and hydrates of any of the foregoing compounds. The products have antibacterial activity.

  通式如下的碳青霉烯类化合物 其中 R 是氢或羧酸保护基；R1 选自氢、低级烷基、低级烷氧基和羟基烷基组成的组；R2 和 R3 各自独立地是氢、低级烷基、低级烷氧基或低级烷硫基；Y 是 (i) 酯基 (ii) 硫酯基团 (iii) 由哌嗪基或吡咯烷基衍生的氨基甲酸酯基团 (iv) 由哌嗪基衍生的胺基团 (v) 由哌嗪基衍生的季铵基团；或 (vi) 包含共价键的基团； 酯基和硫酯基与取代的喹啉基或萘啶基结合；由哌嗪基或吡咯烷基衍生的氨基甲酸酯基团、由哌嗪基衍生的胺基团和由哌嗪基衍生的季铵盐基团含有一个哌嗪基核或一个吡咯烷基核，其氮原子直接与取代的喹啉基或萘啶基键合，哌嗪基和吡咯烷基核未被取代或被一个或多个低级烷基取代；相应基团的共价键通过异噻唑或异噁唑核中的氮原子与取代的异噻唑或异噁唑喹啉基或萘啶基相连； 以及上述任何化合物的相应易水解酯、药学上可接受的盐和水合物。 这些产品具有抗菌活性。
• Dual-action penems and carbapenems
  作者：Alfred J. Corraz、Scott L. Dax、Norma K. Dunlap、Nafsika H. Georgopapadakou、Dennis D. Keith、David L. Pruess、Pamela L. Rossman、Rudolf Then、Joel Unowsky、Chung Chen Wei

  DOI：10.1021/jm00088a019

  日期：1992.5

  Two new series of dual-action antibacterial agents were synthesized in which penems and carbapenems were linked at the 2'-position to quinolones through either an ester or a carbamate moiety. Potent, broad-spectrum antibacterial activity was observed for both classes of compounds, indicative of a dual-mode of action.
• US5147871A
  申请人：——

  公开号：US5147871A

  公开（公告）日：1992-09-15
• Cephalosporin 3'-quinolone esters with a dual mode of action
  作者：Harry A. Albrecht、George Beskid、Ka Kong Chan、James G. Christenson、Roy Cleeland、Kenneth H. Deitcher、Nafsika H. Georgopapadakou、Dennis D. Keith、David L. Pruess

  DOI：10.1021/jm00163a013

  日期：1990.1

  According to the generally accepted mechanism by which bacterial enzymes react with cephalosporins, opening of the beta-lactam ring can lead to the expulsion of a 3'-substituent. A series of dual-action cephalosporins was prepared in which antibacterial quinolones were linked to the cephalosporin 3'-position through an ester bond in the expectation that, in addition to exerting their own beta-lactam activity, these cephalosporins would act as prodrugs for the second antibacterial agent. Compared to parent cephalosporins in which the 3'-substituent was acetoxy, the bifunctional cephalosporins exhibited a broadened antibacterial spectrum, suggesting that a dual mode of action may indeed be operative.