7-[bis(tert-butoxycarbonyl)methyl]-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | 1339953-76-2

• 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-[bis(tert-butoxycarbonyl)methyl]-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• CAS: 1339953-76-2
• 化学式: C₂₄H₂₇FN₂O₉
• 分子量: 506.485
• InChiKey: TZRXBLKCJDAHBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  155.04
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  7-[bis(tert-butoxycarbonyl)methyl]-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 7-(carboxymethyl)-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Heterocycles [h]-Fused to 4-Oxoquinoline-3-carboxylic Acid. Part IX. Synthesis of 2,6-Dioxotetrahydro-1H-pyrrolo[3,2-h]quinoline-7-carboxylic Acid

  摘要：

  Interaction of deprotonated malonic esters with 7-chloro-8-nitro-4-oxoquinoline-3-carboxylate (1) gave the respective 7-[bis(alkoxycarbonyl)methyl] derivatives (2, 3) which were converted into the corresponding 7-(carboxymethyl)-8-nitro-4-oxoquinoline-3-carboxylic acid (4). Reductive lactamization of the latter furnished the target tetrahydro-2,6-dioxo-1H-pyrrolo-[3,2-h]quinoline-7-carboxylic acid (5). Both compounds 4 and 5 exhibited broad spectrum of high antibacterial activity against representatives of Gram-negative and Gram-positive bacteria classes, but were less potent than the reference ciprofloxacin.

  DOI：

  10.3987/com-11-12274
• 作为产物：
  描述：

  丙二酸二叔丁酯 、 7-氯-1-环丙基-6-氟-8-硝基-4-氧代-1,4-二氢喹啉-3-羧酸 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 24.0h， 生成 7-[bis(tert-butoxycarbonyl)methyl]-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Heterocycles [h]-Fused to 4-Oxoquinoline-3-carboxylic Acid. Part IX. Synthesis of 2,6-Dioxotetrahydro-1H-pyrrolo[3,2-h]quinoline-7-carboxylic Acid

  摘要：

  Interaction of deprotonated malonic esters with 7-chloro-8-nitro-4-oxoquinoline-3-carboxylate (1) gave the respective 7-[bis(alkoxycarbonyl)methyl] derivatives (2, 3) which were converted into the corresponding 7-(carboxymethyl)-8-nitro-4-oxoquinoline-3-carboxylic acid (4). Reductive lactamization of the latter furnished the target tetrahydro-2,6-dioxo-1H-pyrrolo-[3,2-h]quinoline-7-carboxylic acid (5). Both compounds 4 and 5 exhibited broad spectrum of high antibacterial activity against representatives of Gram-negative and Gram-positive bacteria classes, but were less potent than the reference ciprofloxacin.

  DOI：

  10.3987/com-11-12274