1,4-dihydro-6,7-dihydroxy-4-oxoquinoline-2-carboxylic acid | 122234-44-0

• 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: 1,4-dihydro-6,7-dihydroxy-4-oxoquinoline-2-carboxylic acid
• 英文别名: 6,7-dihydroxy-4-oxo-1H-quinoline-2-carboxylic acid
• CAS: 122234-44-0
• 化学式: C₁₀H₇NO₅
• 分子量: 221.169
• InChiKey: LRNMFEUNTJOIAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-dihydro-6,7-dihydroxy-4-oxoquinoline-2-carboxylic acid 、 3-(aminomethyl)-7-<2-(2-aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>ceph-3-em-4-carboxylic acid 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 生成 (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-1-carboxy-1-methyl-ethoxyimino]-acetylamino}-3-{[(6,7-dihydroxy-4-oxo-1,4-dihydro-quinoline-2-carbonyl)-amino]-methyl}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of cephalosporins with C-3' catechol-containing residues

  摘要：

  Cephalosporins with new catechol substituents at C-3' have been synthesized, including novel compounds with C-3' carbon-carbon bonds. Many of these compounds have high potency against Gram-negative bacteria, in particular against resistant strains like Pseudomonas aeruginosa. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-3' catechol and also in terms of steric and conformational factors of the C-3' substituent. The best overall properties were found in compounds with a bulky and/or conformationally restricted acidic C-3' catechol.

  DOI：

  10.1021/jm00092a014

文献信息

• US5019570A
  申请人：——

  公开号：US5019570A

  公开（公告）日：1991-05-28
• US5232918A
  申请人：——

  公开号：US5232918A

  公开（公告）日：1993-08-03
• US5371220A
  申请人：——

  公开号：US5371220A

  公开（公告）日：1994-12-06
• Synthesis and structure-activity relationships of cephalosporins with C-3' catechol-containing residues
  作者：J. C. Arnould、A. Bertrandie、T. G. C. Bird、D. Boucherot、F. Jung、J. J. Lohmann、A. Olivier、J. P. Bailey、W. Bell、G. M. Davies

  DOI：10.1021/jm00092a014

  日期：1992.7

  Cephalosporins with new catechol substituents at C-3' have been synthesized, including novel compounds with C-3' carbon-carbon bonds. Many of these compounds have high potency against Gram-negative bacteria, in particular against resistant strains like Pseudomonas aeruginosa. Structure-activity relationships are discussed in terms of their dependence on the pK(a) of the C-3' catechol and also in terms of steric and conformational factors of the C-3' substituent. The best overall properties were found in compounds with a bulky and/or conformationally restricted acidic C-3' catechol.