ethyl 1-(4-fluorophenyl)-7-chloro-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylate | 148927-35-9

• 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: ethyl 1-(4-fluorophenyl)-7-chloro-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylate
• 英文别名: Ethyl 7-chloro-1-(4-fluorophenyl)-6-nitro-4-oxoquinoline-3-carboxylate
• CAS: 148927-35-9
• 化学式: C₁₈H₁₂ClFN₂O₅
• 分子量: 390.755
• InChiKey: WGDWPSAYKGCTJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 1-(4-fluorophenyl)-7-chloro-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylate 在 盐酸 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 7-chloro-1-(4-fluorophenyl)-1,4-dihydro-6-nitro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of 1-substituted 6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acids as potential antimicrobial drugs

  摘要：

  DOI：

  10.1007/bf02464104
• 作为产物：
  描述：

  ethyl ester of 3-dimethylamino-2-(5-nitro-2,4-dichlorobenzoyl)acrylic acid 在 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 ethyl 1-(4-fluorophenyl)-7-chloro-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis of 1-substituted 6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acids as potential antimicrobial drugs

  摘要：

  DOI：

  10.1007/bf02464104

文献信息

• 6-Aminoquinolones: A New Class of Quinolone Antibacterials?
  作者：Violetta Cecchetti、Sergio Clementi、Gabriele Cruciani、Arnaldo Fravolini、Pier Giuseppe Pagella、Angela Savino、Oriana Tabarrini

  DOI：10.1021/jm00006a017

  日期：1995.3

  acids, designed by previous QSAR studies and characterized by an amino group at the C-6 position instead of the usual fluorine atom, were synthesized for the first time and evaluated for in vitro antibacterial activity. All of the synthesized compounds maintain good activity against Gram-negative bacteria (Pseudomonas aeruginosa excluded), and those compounds having a thiomorpholine group as the C-7 substituent

  通过先前的QSAR研究设计了一系列喹诺酮和1,8-萘啶酮-3-羧酸，它们的特征是在C-6位置的氨基而不是通常的氟原子，并进行了首次体外抗菌活性。所有合成的化合物都对革兰氏阴性菌保持良好的活性（铜绿假单胞菌除外），并且具有硫吗啉基作为C-7取代基的那些化合物也对革兰氏阳性菌具有良好的活性。还讨论了与C-1，C-5，C-7和C-8取代基相关的结构活性关系的某些方面。衍生物18g和38g对革兰氏阴性菌和革兰氏阳性菌分别具有0.45和0.66-0.76微克/ mL的几何平均MIC的最佳活性。这种抗菌活性反映了它们抑制细菌DNA旋转酶的能力。这项研究的结果表明，尽管C-6氟仍然是优选的取代基，但仍可通过用氨基取代而获得良好的活性。
• Structure Modifications of 6-Aminoquinolones with Potent Anti-HIV Activity
  作者：Oriana Tabarrini、Miguel Stevens、Violetta Cecchetti、Stefano Sabatini、Micaela Dell'Uomo、Giuseppe Manfroni、Manlio Palumbo、Christophe Pannecouque、Erik De Clercq、Arnaldo Fravolini

  DOI：10.1021/jm049721p

  日期：2004.10.1

  We have recently discovered that 6-aminoquinolone derivatives could be valid leads for the development of new anti-HIV agents because of their new and diversified mode of action. In fact, studies carried out on the lead WM5 showed that this derivative is able to inhibit the Tat-mediated long terminal repeat driven transcription, an essential step in the HIV-1 replication cycle. Thus, starting from lead WM5, we performed the design and synthesis of an enlarged series of 6-aminoquinolones, which permitted some very potent anti-HIV 6-amino derivatives to be obtained and the structure-activity relationship to be delineated. Some derivatives, 26c, 26e, 26i, and 26j, proved to be highly effective in inhibiting HIV replication at 50% inhibitory concentration in the range of 0.0087-0.7 mug/mL in MT-4, PBMCs and CEM cell lines coupled with positive selectivity indexes that reach values higher than 1000 on CEM cell lines for compounds 26e and 26i. Time-of-addition experiments clearly confirm that the new, potent 6-aminoquinolones interact at a postintegration step in the replication cycle of HIV.
• Synthesis and antimycobacterial activities of novel 6-nitroquinolone-3-carboxylic acids
  作者：Palaniappan Senthilkumar、Murugesan Dinakaran、Perumal Yogeeswari、Dharmarajan Sriram、Arnab China、Valakunja Nagaraja

  DOI：10.1016/j.ejmech.2008.02.031

  日期：2009.1

  Various 1-(substituted)-1,4-dihydro-6-nitro-4-oxo-7-(sub-secondary amino)-quinoline-3-carboxylic acids were synthesized from 2,4-dichlorobenzoic acid by six step synthesis. The compounds were evaluated for antimycobacterial in vitro and in vivo against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant Mycobacterium tuberculosis (MDR-TB) and Mycobacterium smegmatis (MC2) and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from M. smegmatis. Among the 48 synthesized compounds, 7-(4-((benzo[d][1,3]dioxol-5-yl)methyl)piperazin-1-yl)-1-cyclopropyl-1,4-dihydro-6-nitro-4-oxoquinotine-3-carboxylic acid (8c) was found to be the most active compound in vitro with MIC of 0.08 and 0.16 mu M against MTB and MDR-TB, respectively. In the in vivo animal model 8c decreased the bacterial load in lung and spleen tissues with 2.78 and 4.15-log 10 protections, respectively, at the dose of 50 mg/kg body weight. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Synthesis of 1-substituted 6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acids as potential antimicrobial drugs
  作者：R. G. Glushkov、N. B. Marchenko、I. B. Levshin

  DOI：10.1007/bf02464104

  日期：1997.5