1-Ethyl-6-fluoro-4-oxo-7-pyrrol-1-yl-1,4-dihydro-quinoline-3-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 | 122949-37-5

• 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: 1-Ethyl-6-fluoro-4-oxo-7-pyrrol-1-yl-1,4-dihydro-quinoline-3-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: prop-2-enyl (6R,7R)-3-[(1-ethyl-6-fluoro-4-oxo-7-pyrrol-1-ylquinoline-3-carbonyl)oxymethyl]-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 122949-37-5
• 化学式: C₃₅H₃₁FN₄O₈S
• 分子量: 686.718
• InChiKey: CWILMTITFLPZQS-CYTLCNBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-Ethyl-6-fluoro-4-oxo-7-pyrrol-1-yl-1,4-dihydro-quinoline-3-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-<<<<1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1H-pyrrol-1-yl)quinolin-3-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; 1-ethyl-6-fluoro-4-oxo-7-pyrrol-1-yl-1,4-dihydro-quinoline-3-carboxylate 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以47%的产率得到1-Ethyl-6-fluoro-4-oxo-7-pyrrol-1-yl-1,4-dihydro-quinoline-3-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：——