5-(4-Fluoro-phenyl)-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid (6R,7R)-2-allyloxycarbonyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester | 115622-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5-(4-Fluoro-phenyl)-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid (6R,7R)-2-allyloxycarbonyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester
• 英文别名: [(6R,7R)-8-oxo-7-[(2-phenoxyacetyl)amino]-2-prop-2-enoxycarbonyl-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl 5-(4-fluorophenyl)-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate
• CAS: 115622-79-2
• 化学式: C₃₆H₂₈FN₃O₁₀S
• 分子量: 713.697
• InChiKey: QJZNKARLPGATET-KAODMTDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  51
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  175
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  5-(4-Fluoro-phenyl)-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid (6R,7R)-2-allyloxycarbonyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester 在 palladium diacetate 、 亚磷酸三乙酯 、 sodium 2-ethylhexanoic acid 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 (6R-trans)-3-<<<<5-(4-fluorophenyl)-5,8-dihydro-8-oxo-1,3-dioxolo<4,5-g>quinolin-7-yl>carbonyl>oxy>methyl>-8-oxo-7-<(phenoxyacetyl)amino>-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid sodium salt
  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
• 作为产物：
  描述：

  (6R-trans)-3-(iodomethyl)-8-oxo-7-<(phenoxyacetyl)amino>-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid allyl ester 、 Sodium; 5-(4-fluoro-phenyl)-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以36%的产率得到5-(4-Fluoro-phenyl)-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid (6R,7R)-2-allyloxycarbonyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester
  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

• ALBRECHT, HARRY A.;BESKID, GEORGE;CHAN, KA-KONG;CHRISTENSON, JAMES G.;CLE+, J. MED. CHEM., 33,(1990) N, C. 77-86
  作者：ALBRECHT, HARRY A.、BESKID, GEORGE、CHAN, KA-KONG、CHRISTENSON, JAMES G.、CLE+

  DOI：——

  日期：——