7-氯-1-乙基-1,4-二氢-4-氧代-6-(1-哌嗪基)喹啉-3-羧酸 | 75001-78-4

• 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
• 中文名称: 7-氯-1-乙基-1,4-二氢-4-氧代-6-(1-哌嗪基)喹啉-3-羧酸
• 中文别名: 诺氟沙星EP杂质E；7-氯-1-乙基-1,4-二氢-4-氧代-6-(1-哌嗪基)-3-喹啉羧酸
• 英文名称: 7-chloro-1-ethyl-1,4-dihydro-4-oxo-6-(1-piperazinyl)quinoline-3-carboxylic acid
• 英文别名: Unii-8KN2CM9HX2；7-chloro-1-ethyl-4-oxo-6-piperazin-1-ylquinoline-3-carboxylic acid
• CAS: 75001-78-4
• 化学式: C₁₆H₁₈ClN₃O₃
• 分子量: 335.79
• InChiKey: UMTPEXSEHSNOKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  272-273 °C
• 沸点：
  586.4±50.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)
• 溶解度：
  可微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7-氯-1-乙基-6-氟-4-氧氢喹啉-3-羧酸 、 哌嗪 以25%的产率得到
  参考文献：
  名称：

  KOGA, HIROSHI;ITOH, AKIRA;MURAYAMA, SATOSHI;SUZUE, SEIGO;IRIKURA, TSUTOMU, J. MED. CHEM., 1980, 23, N 12, 1358-1363

  摘要：

  DOI：

文献信息

• CONVENIENT ONE POT SYNTHESIS OF SOME FLUOROQUINOLONES IN AQUEOUS MEDIA
  作者：M. Saeed Abaee、Ruhollah Shariti、Shahin Borhani、Majid Μ. Heravi、Hossein Motahari

  DOI：10.1515/hc.2005.11.5.415

  日期：2005.1

  gyrase inhibition (8). Recently, more highly effective broad-spectrum antibacterial agents containing fluorine atom at C 6 have been synthesized. Solid phase synthesis (9-10) and microwave preparation (11-12) o f some examples are also reported. Some general examples are ciprofloxacin (13), norfloxacin (14), enrofloxacin (15), and Pefloxacin (16) with the structures illustrated in Scheme-1. nornoxacin:

  介绍了一种从 1 制备氟喹诺酮类的一锅法合成策略。产物 i 在水性介质中与哌嗪缩合，以 8 6 % 的收率生产医药级环丙沙星。该方法扩展到其他一些具有医药级质量的氟喹诺酮类药物的合成。关键词：环丙沙星、恩诺沙星、诺氟沙星、培氟沙星、氟喹诺酮类。简介 氟喹诺酮类是合成抗生素 (1-7)，含有喹诺酮结构，对多种革兰氏阳性菌和革兰氏阴性菌有效。它们通过抑制 DNA 旋转酶来中断细菌 DNA 的产生 (8)。最近，已经合成了在C 6 处含有氟原子的更高效的广谱抗菌剂。还报道了一些实施例的固相合成(9-10)和微波制备(11-12)。一些一般实例是环丙沙星 (13)、诺氟沙星 (14)、恩诺沙星 (15) 和培氟沙星 (16)，其结构如方案 1 所示。诺诺沙星：κ = κ = i-哌嗪；penoxacin：λ — *-25ι Λ ~~ f-incmyi-1 pipcrazuiyi Scheme-1
• Regioselective Nucleophilic Substitution of Halogen Derivatives of 1-Substituted 4-Oxo-1,4-dihydroquinoline-3-carboxylic Acids
  作者：István Hermecz、Lelle Vasvári-Debreczy、Benjamin Podányi、Géza Kereszturi、Mária Balogh、Ágnes Horváth、Péter Várkonyi

  DOI：10.3987/com-98-8143

  日期：——

  The rate of the nucleophilic displacement of the fluoro atom of 7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate could be enhanced either by the introduction of further fluoro atom(s) into position(s) 6 and/or 8, or by the formation of a boron chelate (e.g. 3). The regioselectivity of the nucleophilic substitution of the chloro atom in 1-substituted 6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acids could also be enhanced by the formation of a boron chelate (e.g. 7).
• Quinolone antibiotics: Study of reactivity and impurity profile of piperazine with chloro-fluoro-quinolone carboxylic acid in aqueous medium
  作者：U.R. Kalkote、V.T. Sathe、R.K. Kharul、S.P. Chavan、T. Ravindranathan

  DOI：10.1016/s0040-4039(96)01477-3

  日期：1996.9

  The reaction of 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,2-dihydroquinoline-3- carboxylic acid with piperazine in water was studied. The product ciprofloxacin was isolated and the impurity formed in the reaction was isolated and characterized as 1-cyclopropyl-7-chloro-6-piperazinyl-4-oxo-1,2-dihydroquinoline-3-carboxylic acid. Similarly norfloxacin was also synthesised. Copyright (C) 1996 Published by Elsevier Science Ltd