7-(carboxymethyl)-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | 1339953-73-9

• 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-(carboxymethyl)-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 7-(Carboxymethyl)-1-cyclopropyl-6-fluoro-8-nitro-4-oxoquinoline-3-carboxylic acid
• CAS: 1339953-73-9
• 化学式: C₁₅H₁₁FN₂O₇
• 分子量: 350.26
• InChiKey: NXCNMZYKRUOGCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  7-(carboxymethyl)-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 在 sodium dithionite 、 potassium carbonate 、 盐酸 作用下， 以 水 为溶剂， 以63%的产率得到9-cyclopropyl-4-fluoro-2,3,6,9-tetrahydro-2,6-dioxo-1H-pyrrolo[3,2-h]quinoline-7-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：

  ethyl 7-[bis(tert-butoxycarbonyl)methyl]-1-cyclopropyl-6-fluoro-8-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 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

文献信息

• 一类新喹诺酮衍生物
  申请人：北京虹湾医药技术有限公司

  公开号：CN102603731B

  公开（公告）日：2016-03-16

  本发明涉及一种具有优越抗菌活性的喹诺酮衍生物，它显示了优异的抗菌活性，还有很宽的抗菌谱，尤其是具有很强的抗革兰氏阳性菌活性；本发明还涉及该喹诺酮衍生物的制备方法，和含有该喹诺酮衍生物或其盐、酯或溶剂化物作为活性成分的药物组合物，以及该喹诺酮衍生物或其盐、酯或溶剂化物在制备用作抗菌剂药物中的用途。