(-)-7-<4-(ethoxycarbonyl)piperazino>-6-fluoro-1-<(1'S,2'R)-2'-phenylcyclopropyl>-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl piperazinecarboxylate salt | 103531-45-9

• 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: (-)-7-<4-(ethoxycarbonyl)piperazino>-6-fluoro-1-<(1'S,2'R)-2'-phenylcyclopropyl>-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl piperazinecarboxylate salt
• 英文别名: (-)-7-[4-(ethoxycarbonyl)piperazino]-6-fluoro-1-((1'S,2'R)-2'-phenylcyclopropyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl piperazinecarboxylate salt
• CAS: 103531-45-9
• 化学式: C₂₆H₂₆FN₃O₅
• 分子量: 479.508
• InChiKey: BEGBLKQKWZDNAI-UTKZUKDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  92.08
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (-)-7-<4-(ethoxycarbonyl)piperazino>-6-fluoro-1-<(1'S,2'R)-2'-phenylcyclopropyl>-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl piperazinecarboxylate salt 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以56%的产率得到(-)-6-fluoro-1-<(1'S,2'R)-2'-phenylcyclopropyl>-7-piperazino-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Chiral DNA gyrase inhibitors. 1. Synthesis and antimicrobial activity of the enantiomers of 6-fluoro-7-(1-piperazinyl)-1-(2-trans-phenylcyclopropyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

  摘要：

  New quinolone antimicrobial agents (racemic, (1'S,2'R)- and (1'R,2'S)-6-fluoro-7-(1-piperazinyl)-1-(2'-trans-phenyl-1'-cyclopropyl)- 1, 4-dihydro-4-oxoquinoline-3-carboxylic acids) were synthesized, and their in vitro antimicrobial potencies and spectra were determined. As compared to their conceptual parents, these agents retained a considerable amount of the antimicrobial potency and spectra of ciprofloxacin and of 6-fluoro-1-phenyl-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxy lic acid against Gram-positives. Gram-negatives were considerably less sensitive. The (-)-(1'S,2'R) analogue was the more potent of the enantiomers, but the degree of chiral discrimination by most bacteria was only 4-fold. The 4-fold chiral discrimination was observed also using purified DNA gyrase obtained from Micrococcus luteus, whereas the two enantiomers were essentially equiactive against the enzyme derived from Escherichia coli. These results confirm that there is a substantial degree of bulk tolerance available at N-1 of quinolone antimicrobial agents and suggest that electronic factors controlled by substitution at that site are of considerable importance. On the other hand, chiral recognition brought about by attachment of optically active groups to the N-1 position in these derivatives is relatively small.

  DOI：

  10.1021/jm00160a042
• 作为产物：
  描述：

  (1S,2R)-2-苯基环丙胺 在 氢氧化钾 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 (-)-7-<4-(ethoxycarbonyl)piperazino>-6-fluoro-1-<(1'S,2'R)-2'-phenylcyclopropyl>-1,4-dihydro-4-oxoquinoline-3-carboxylic acid ethyl piperazinecarboxylate salt
  参考文献：
  名称：

  Chiral DNA gyrase inhibitors. 1. Synthesis and antimicrobial activity of the enantiomers of 6-fluoro-7-(1-piperazinyl)-1-(2-trans-phenylcyclopropyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

  摘要：

  New quinolone antimicrobial agents (racemic, (1'S,2'R)- and (1'R,2'S)-6-fluoro-7-(1-piperazinyl)-1-(2'-trans-phenyl-1'-cyclopropyl)- 1, 4-dihydro-4-oxoquinoline-3-carboxylic acids) were synthesized, and their in vitro antimicrobial potencies and spectra were determined. As compared to their conceptual parents, these agents retained a considerable amount of the antimicrobial potency and spectra of ciprofloxacin and of 6-fluoro-1-phenyl-7-(1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxy lic acid against Gram-positives. Gram-negatives were considerably less sensitive. The (-)-(1'S,2'R) analogue was the more potent of the enantiomers, but the degree of chiral discrimination by most bacteria was only 4-fold. The 4-fold chiral discrimination was observed also using purified DNA gyrase obtained from Micrococcus luteus, whereas the two enantiomers were essentially equiactive against the enzyme derived from Escherichia coli. These results confirm that there is a substantial degree of bulk tolerance available at N-1 of quinolone antimicrobial agents and suggest that electronic factors controlled by substitution at that site are of considerable importance. On the other hand, chiral recognition brought about by attachment of optically active groups to the N-1 position in these derivatives is relatively small.

  DOI：

  10.1021/jm00160a042