(6R-trans)-4-<3-carboxy-6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxoquinolin-7-yl>-1-<<2-carboxy-8-oxo-7-<(phenoxyacetyl)amino>-5-thia-1-azabicyclo<4.2.0>oct-2-en-3-yl>methyl>-1-methylpiperazinium iodide | 127142-75-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (6R-trans)-4-<3-carboxy-6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxoquinolin-7-yl>-1-<<2-carboxy-8-oxo-7-<(phenoxyacetyl)amino>-5-thia-1-azabicyclo<4.2.0>oct-2-en-3-yl>methyl>-1-methylpiperazinium iodide
• 英文别名: [6R-(6α,7β)]-4-[3-carboxy-1-(2-fluoroethyl)-6,8-difluoro-1,4-dihydro-4-oxoquinolin-7-yl]-[[2-carboxy-8-oxo-7-[(phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-1-methylpiperazinium iodide；[6R-trans]-4-[3-carboxy-1-(2-fluoroethyl)-6,8-difluoro-1,4-dihydro-4-oxoquinolin-7-yl]-1-[[2-carboxy-8-oxo-7-[(phenoxyacetyl)amino]-5-thia-1-azabicyclo-[4.2.0]oct-2-en-3-yl]methyl]-1-methylpiperazinium iodide；(6R,7R)-3-[[4-[3-carboxy-6,8-difluoro-1-(2-fluoroethyl)-4-oxoquinolin-7-yl]-1-methylpiperazin-1-ium-1-yl]methyl]-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;iodide
• CAS: 127142-75-0
• 化学式: C₃₃H₃₃F₃N₅O₈S*I
• 分子量: 843.619
• InChiKey: LTWPPUGHNDGYKK-SGXBNLSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.96
• 重原子数：
  51
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  182
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  (6R)-3-acetoxymethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 在 四氢呋喃 、 甲醇 、 碘代三甲硅烷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 (6R-trans)-4-<3-carboxy-6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxoquinolin-7-yl>-1-<<2-carboxy-8-oxo-7-<(phenoxyacetyl)amino>-5-thia-1-azabicyclo<4.2.0>oct-2-en-3-yl>methyl>-1-methylpiperazinium iodide
  参考文献：
  名称：

  Dual-action cephalosporins: cephalosporin 3'-quaternary ammonium quinolones

  摘要：

  When cephalosporins exert their biological activity by reacting with bacterial enzymes, opening of the beta-lactam ring can lead to expulsion of the 3'-substituent. A series of cephalosporins was prepared in which antibacterial quinolones were linked to the 3'-position through a quaternary nitrogen. Like the 3'-ester-linked dual-action cephalosporins reported earlier, these compounds demonstrated a broad spectrum of antibacterial activity derived from cephalosporin-like and quinolone-like components, suggesting a dual mode of action.

  DOI：

  10.1021/jm00106a031

文献信息

• Antibacterial cephalosporin compounds
  申请人：Hoffmann-La Roche Inc.

  公开号：US05329002A1

  公开（公告）日：1994-07-12

  There are presented antibacterial cephalosporins having broad antimicrobial activity as well as intermediates for their formation, such compounds having the formula ##STR1## wherein R is hydrogen or a carboxylic acid-protecting group; R.sub.1 is a substituted piperazinium group of the formula ##STR2## in which Q represents a substituted quinolinyl or naphthyridinyl group and the piperazine nucleus may be optionally substituted with one or more lower alkyl groups; R.sub.2 is selected from the group consisting of hydrogen, lower alkoxy, lower alkylthio and amido; R.sub.3 is hydrogen or an acyl group; and m is 0, 1 or 2, preferably 0; as well as the corresponding readily hydrolyzable esters, pharmaceutically acceptable salts and hydrates of these compounds.

  本发明提供了具有广谱抗微生物活性的抗菌头孢菌素以及它们的中间体，这些化合物具有以下式子：##STR1## 其中R为氢或羧基保护基；R.sub.1为以下式子的取代哌嗪基：##STR2## 其中Q代表取代的喹啉基或萘啉基，哌嗪核可以选择性地取代一个或多个较低的烷基基团；R.sub.2选自氢、较低的烷氧基、较低的烷基硫基和酰胺基的群；R.sub.3为氢或酰基基团；m为0、1或2，优选为0；以及这些化合物的相应易于水解的酯、药学上可接受的盐和水合物。
• ALBRECHT, HARRY A.;BESKID, GEORGE;CHRISTENSON, JAMES G.;DURKIN, JOANNE W.+, J. MED. CHEM., 34,(1991) N, C. 669-675
  作者：ALBRECHT, HARRY A.、BESKID, GEORGE、CHRISTENSON, JAMES G.、DURKIN, JOANNE W.+

  DOI：——

  日期：——
• Cephalosporinderivate
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0335297B1

  公开（公告）日：1996-03-13
• US5329002A
  申请人：——

  公开号：US5329002A

  公开（公告）日：1994-07-12
• Dual-action cephalosporins: cephalosporin 3'-quaternary ammonium quinolones
  作者：Harry A. Albrecht、George Beskid、James G. Christenson、Joanne W. Durkin、Virve Fallat、Nafsika H. Georgopapadakou、Dennis D. Keith、Frederick M. Konzelmann、Ellen R. Lipschitz

  DOI：10.1021/jm00106a031

  日期：1991.2

  When cephalosporins exert their biological activity by reacting with bacterial enzymes, opening of the beta-lactam ring can lead to expulsion of the 3'-substituent. A series of cephalosporins was prepared in which antibacterial quinolones were linked to the 3'-position through a quaternary nitrogen. Like the 3'-ester-linked dual-action cephalosporins reported earlier, these compounds demonstrated a broad spectrum of antibacterial activity derived from cephalosporin-like and quinolone-like components, suggesting a dual mode of action.