1-ethyl-6-nitro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester | 70186-33-3

• 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: 1-ethyl-6-nitro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl ester of 1-ethyl-6-nitro-4-oxo-7-chloro-1,4-dihydroquinoline-3-carboxylic acid；ethyl 7-chloro-1-ethyl-6-nitro-1H-quinolin-4-one-3-carboxylate；ethyl 1-ethyl-6-nitro-7-chloro-4-quinolone-3-carboxylate；Ethyl 7-chloro-1-ethyl-6-nitro-4-oxo-1,4-dihydro-3-quinolinecarboxylate；ethyl 7-chloro-1-ethyl-6-nitro-4-oxoquinoline-3-carboxylate
• CAS: 70186-33-3
• 化学式: C₁₄H₁₃ClN₂O₅
• mdl: MFCD01090654
• 分子量: 324.721
• InChiKey: FDZUDEZZPLTYAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  1-ethyl-6-nitro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 在 palladium on activated charcoal 菲 、 氢气 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 25.0~340.0 ℃ 、101.33 kPa 条件下， 反应 10.25h， 生成 ethyl 1-ethyl-1H,10H-pyrido<2,3-b>carbazol-4-one-3-carboxylate
  参考文献：
  名称：

  Synthesis of Various Pyrido- and Indolo[g]fused 1H-Quinolin-4-one Derivatives

  摘要：

  Four series of linear tricyclic and quadricyclic heterocyclic derivatives related to oxolinic acid have been prepared: 1H-pyrido[3,4-g]quinolin-4-ones (1), 1H-pyrido[3,2-g]quinolin-4-ones (2), 1H,11H-pyrido[3,2-b] acridine-4,6-diones (8)and 1H,10H-indolo[3,2-g]quinolin-4-ones (10).

  DOI：

  10.3987/com-93-6500
• 作为产物：
  描述：

  ethyl 2-(2,4-dichloro-5-nitrobenzoyl)-3-ethoxyacrylate 在 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-ethyl-6-nitro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and amination of 1-alkyl-6-nitro-4-oxo-7-chloro-1,4-dihydroquinoline-3-carboxylic acids

  摘要：

  DOI：

  10.1007/bf02464110

文献信息

• Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids
  作者：Hiroshi Koga、Akira Itoh、Satoshi Murayama、Seigo Suzue、Tsutomu Irikura

  DOI：10.1021/jm00186a014

  日期：1980.12

  Previous quantitative and qualitative structure-activity studies in antibacterial monosubstituted 1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids prompted us to synthesize the 6,7,8-polysubstituted compounds. In this paper, the preparation and antibacterial activity of the 6,7- and 7,8-disubstituted compounds and their derivatives are described. Among these compounds, 1-ethyl-6-fluoro-1,4-di

  先前在抗菌单取代的1-乙基-1,4-二氢-4-氧代喹啉3-羧酸中进行的定量和定性结构活性研究促使我们合成了6,7,8-多取代的化合物。在本文中，描述了6,7-和7,8-二取代化合物及其衍生物的制备和抗菌活性。在这些化合物中，1-乙基-6-氟-1,4-二氢-4-氧代-7-（1-哌嗪基）喹啉-3-羧酸（34）具有许多显着的活性，并且比草酸（ 84）对抗革兰氏阳性和革兰氏阴性细菌。讨论了构效关系。
• Novel synthesis of 3-nitro-4-quinolone derivatives
  作者：M. M. Maslova、N. B. Marchenko、V. I. Po1'shakov、R. G. Glushkov

  DOI：10.1007/bf00781074

  日期：1993.2

  the selective introduction of the nitro group into ~-electron-deficient nitrogen heterocycles has not been clearly resolved to date. This circumstance makes the task of developing preparative methods for the synthesis of 3-nitro-4-quinolones a vital one, as it has been previously. 3-Nitroquinoline derivatives are of interest for pharmacological research as potential drugs and also as convenient key

  将硝基选择性引入到缺电子氮杂环中的问题迄今尚未得到明确解决。这种情况使得开发用于合成 3-硝基-4-喹诺酮类的制备方法的任务成为一项至关重要的任务，就像以前一样。3-硝基喹啉衍生物作为潜在的药物和用于制备生物活性化合物的方便的关键产品在药理学研究中很受关注。
• 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.
• 7-Substituted 6-nitro analogs of oxolinic acid
  作者：R. G. Glushkov、L. N. Dronova、A. S. Elina、M. V. Porokhovaya、E. N. Padeiskaya、T. P. Radkevich、L. D. Shipilova

  DOI：10.1007/bf00764618

  日期：1989.11
• Transformation of bis(2-chloroethyl)amino group into 1-piperazinyl in position 7 in the series of 6-nitroquinolonecarboxylic acid derivatives
  作者：R. G. Glushkov、S. A. Zaitsev、I. B. Levshin、N. B. Marchenko

  DOI：10.1007/bf02464281

  日期：1997.11