1-(叔丁基)-7-氯-6-氟-4-氧代-1,4-二氢喹啉-3-羧酸乙酯 | 116163-44-1

• 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: 1-(叔丁基)-7-氯-6-氟-4-氧代-1,4-二氢喹啉-3-羧酸乙酯
• 英文名称: 1-tert-Butyl-7-chloro-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 1-tert-butyl-7-chloro-6-fluoro-4-oxoquinoline-3-carboxylate
• CAS: 116163-44-1
• 化学式: C₁₆H₁₇ClFNO₃
• 分子量: 325.767
• InChiKey: XFTOZFHJTMQHSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  48.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(叔丁基)-7-氯-6-氟-4-氧代-1,4-二氢喹啉-3-羧酸乙酯 在 吡啶 、 氢氧化钾 作用下， 以 水 为溶剂， 反应 19.5h， 生成 1-(tert-butyl)-7-(piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationship of new 1-substituted derivatives

  摘要：

  A series of novel 7-piperazinyl-1-substituted-6-fluoroquinolones and naphthyridines have been prepared and their antibacterial activities evaluated. These derivatives are characterized by having alkyl, alkenyl, arylalkyl, cycloalkyl, and cycloalkenyl groups at the 1-position. As a result of this study, derivatives 7 and 26, which are substituted with tert-butyl groups at N-1, were found to possess excellent in vitro and in vivo potency, particularly against Staphylococcus aureus, comparable to that of norfloxacin or ciprofloxacin. Structure-activity relationships of N-1 substituted alkyls and cycloalkyls are also discussed.

  DOI：

  10.1021/jm00123a005
• 作为产物：
  描述：

  3-(2,4-dichloro-5-fluorophenyl)-3-oxo-2-(((1,1-dimethylethyl)amino)methylene)propanoic acid etyhyl ester 在 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-(叔丁基)-7-氯-6-氟-4-氧代-1,4-二氢喹啉-3-羧酸乙酯
  参考文献：
  名称：

  Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationship of new 1-substituted derivatives

  摘要：

  A series of novel 7-piperazinyl-1-substituted-6-fluoroquinolones and naphthyridines have been prepared and their antibacterial activities evaluated. These derivatives are characterized by having alkyl, alkenyl, arylalkyl, cycloalkyl, and cycloalkenyl groups at the 1-position. As a result of this study, derivatives 7 and 26, which are substituted with tert-butyl groups at N-1, were found to possess excellent in vitro and in vivo potency, particularly against Staphylococcus aureus, comparable to that of norfloxacin or ciprofloxacin. Structure-activity relationships of N-1 substituted alkyls and cycloalkyls are also discussed.

  DOI：

  10.1021/jm00123a005

文献信息

• Fluoronaphthyridines and quinolones as antibacterial agents. 2. Synthesis and structure-activity relationships of new 1-tert-butyl 7-substituted derivatives
  作者：D. Bouzard、P. Di Cesare、M. Essiz、J. P. Jacquet、J. R. Kiechel、P. Remuzon、A. Weber、T. Oki、M. Masuyoshi

  DOI：10.1021/jm00167a010

  日期：1990.5

  A number of 7-substituted-1-tert-butyl-6-fluoroquinolone-3-carboxylic acids and 7-substituted-1-tert-butyl-6-fluoro-1,8-naphthyridine-3-carboxylic acids have been prepared and tested for antibacterial activities. Among those the 7-aminopyrrolidinyl 20b and the 7-diazabicyclo naphthyridine 18b are the most potent compounds in vitro and in vivo. Physicochemical data and acute toxicity are also discussed

  已经制备了许多7-取代的1-叔丁基-6-氟喹诺酮-3-羧酸和7-取代的1-叔丁基-6-氟-1,8-萘啶-3-羧酸。经测试具有抗菌活性。其中7-氨基吡咯烷基20b和7-二氮杂双环萘啶18b是体外和体内最有效的化合物。还讨论了理化数据和急性毒性。考虑到体外和体内的微生物活性，低毒性和药代动力学特征，化合物18b BMY 40062表现出最有利的总体性能，并被选择用于临床评估。
• 6-Aminoquinolones as New Potential Anti-HIV Agents
  作者：Violetta Cecchetti、Cristina Parolin、Stefano Moro、Teresa Pecere、Enrica Filipponi、Arianna Calistri、Oriana Tabarrini、Barbara Gatto、Manlio Palumbo、Arnaldo Fravolini、Giorgio Palu’

  DOI：10.1021/jm9903390

  日期：2000.10.1

  A series of 6-aminoquinolone compounds were evaluated for their in vitro activity against human immunodeficiency virus type 1 (HIV-1). Compound 12a, bearing a methyl substituent at the N-1 position and a 4-(2-pyridyl)-1-piperazine moiety at the C-7 position, was the most active in inhibiting HIV-1 replication on de novo infected C8166 human lymphoblastoid cell lines. The 12a EC50 value was 0.1 mu M, a 7-20-fold lower concentration relative to that for compounds 8a and 7a containing a cyclopropyl and tert-butyl substituent at the N-1 position, respectively. When the C-6 amino group was replaced with a fluorine atom, a decreased antiviral effect was observed. The observed effects are selective, since potency is substantially reduced when testing the compounds against the herpes simplex virus type 1 (HSV-1). Active quinolone derivatives very efficiently interact with TAR RNA, which suggests a nucleic acid-targeted mechanism of action.
• Novel fluoroquinolones: design, synthesis, and in vivo activity in mice against Mycobacterium tuberculosis H37Rv
  作者：Anand V. Shindikar、C.L. Viswanathan

  DOI：10.1016/j.bmcl.2005.02.037

  日期：2005.4

  Novel 6,8-difluoro-1-alkyl-5-amino-1,4-dihydro-4-oxo-7-4-substituted piperazin-1-yl}-quinoline-3-carboxylic acids, with the substituents at 4th position of piperazine being -[2(pyridine-4-carbonyl) hydrazono]propyl and -2[(pyrazine-2-carbonyl) amino] ethyl, were synthesized and evaluated in vivo against Mycobacterium tuberculosis H(37)Rv in Swiss albino mice. Test compounds exhibited activity comparable to that of sparfloxacin (survival rate, reduction of splenomegaly and reduced tubercular lesions) at a dose of 200 mg/kg. (c) 2005 Elsevier Ltd. All rights reserved.
• BOUZARD, D.;CESARE, P. DI;ESSIZ, M.;JACQUET, J. P.;KIECHEL, J. R.;REMUZON+, J. MED. CHEM., 33,(1990) N, C. 1344-1352
  作者：BOUZARD, D.、CESARE, P. DI、ESSIZ, M.、JACQUET, J. P.、KIECHEL, J. R.、REMUZON+

  DOI：——

  日期：——