ethyl 7-chloro-6-fluoro-4-oxo-1-(prop-2-yn-1-yl)-1,4-dihydroquinoline-3-carboxylate | 134478-70-9

• 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 7-chloro-6-fluoro-4-oxo-1-(prop-2-yn-1-yl)-1,4-dihydroquinoline-3-carboxylate
• 英文别名: ethyl 7-chloro-6-fluoro-4-oxo-1-prop-2-ynylquinoline-3-carboxylate
• CAS: 134478-70-9
• 化学式: C₁₅H₁₁ClFNO₃
• 分子量: 307.709
• InChiKey: JCXDNWKUPWPDPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  216-220 °C(Solv: ethanol (64-17-5))
• 沸点：
  444.5±45.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 7-chloro-6-fluoro-4-oxo-1-(prop-2-yn-1-yl)-1,4-dihydroquinoline-3-carboxylate 在 盐酸 、 碳酸氢钠 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 9.0h， 生成 7-氯-6-氟-1,4-二氢-4-氧代-1-丙二烯基喹啉-3-羧酸
  参考文献：
  名称：

  Radl, Stanislav; Kovarova, Lenka; Holubek, Jiri, Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 2, p. 439 - 448

  摘要：

  DOI：
• 作为产物：
  描述：

  二乙基[[(3-氯-4-氟苯基)氨基]亚甲基]丙二酸酯 在 sodium hydride 作用下， 以 二苯醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.83h， 生成 ethyl 7-chloro-6-fluoro-4-oxo-1-(prop-2-yn-1-yl)-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis and in vitro antiplasmodial activities of fluoroquinolone analogs

  摘要：

  Fluoroquinolone analogs were synthesized by simple alkylation followed by click chemistry and evaluated for their antimalarial in vitro against chloroquine sensitive strain of Plasmodium falciparum while ciprofloxacin was used as standard. Our results showed that the compound 12 was found most active with IC50 value of 1.33 mu g/mL while ciprofloxacin showed IC50 = 8.81 mu g/mL. Therefore, screening of either known or unknown quinolone/fluoroquinolone analogs are worthwhile to find more potent antimalarial drugs which might prove useful in the treatment of mild or severe malaria in human either alone or in combination with existing antimalarial drugs. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.006

文献信息

• Synthesis of Novel<i>N</i>-Triazolo Methyl Substituted Fluoroquinolones and Their Antimicrobial Activity
  作者：A Ravi Kumar、G. Sathaiah、A. Chandra Shekhar、K. Raju、P. Shanthan Rao、B. Narsaiah、Y. K. Raju、U. S. N. Murthy

  DOI：10.1002/jhet.2034

  日期：2015.1

  strategy was adopted for the preparation of N‐triazolo methyl substituted fluoroquinolones 4 and screened for their antimicrobial activity. The synthetic methodology starts from N‐propargylation of ethyl 7‐chloro‐6‐fluoro‐4‐hydroxyquinoline‐3‐carboxylate (1) followed by reaction with azides through click reaction under Sharpless conditions furnished triazole substituted quinolone ester 3. The latter quinolone

  采用了一种优雅的合成策略来制备N-三唑并甲基取代的氟喹诺酮4并对其抗菌活性进行了筛选。合成方法从7-氯-6-氟-4-羟基喹啉3-羧酸乙酯的N-炔丙基化开始（1），然后在Sharpless条件下通过点击反应与叠氮化物反应，得到三唑取代的喹诺酮酯3。后者的喹诺酮酯与各种仲胺反应，得到相应的喹诺酮衍生物4。或者，喹诺酮羧酸衍生物7a，7b，7c，7d由三唑标记的喹诺酮酯分两步制备。针对各种细菌和真菌菌株筛选所有最终产物。化合物4a，4b，4c和4k显示出中等的抗菌活性，而4f显示出对真菌菌株的有希望的活性。
• Antibiotic protected silver nanoparticles for microbicidal cotton
  作者：Ana Maria Montagut、Albert Granados、Anna Ballesteros、Roser Pleixats、Montserrat Llagostera、Pilar Cortés、Rosa María Sebastián、Adelina Vallribera

  DOI：10.1016/j.tet.2018.11.035

  日期：2019.1

  Surface coating of metal nanoparticles is one of the major aspects to be optimized in the design of antimicrobial nanoparticles. The novelty of this work is that antimicrobial derivatives have been used as stabilizers to protect silver nanoparticles (Ag NPs). Microbicidal activity studies of fabricated cotton textiles coated with these [email protected] were performed. Protective ligand layers of Ag

  金属纳米颗粒的表面涂层是抗菌纳米颗粒设计中要优化的主要方面之一。这项工作的新颖之处在于，抗菌衍生物已被用作稳定剂来保护银纳米颗粒（Ag NPs）。对涂有这些[受电子邮件保护]的人造棉纺织品的杀菌活性进行了研究。Ag NPs的保护性配体层是其抗菌活性的决定性因素。对于织物TAM（用表面上带有三芳基甲烷衍生物的Ag NP涂层，[电子邮件保护]），获得了最佳的杀菌活性，对于金黄色葡萄球菌菌株，细菌减少了3 log个单位。TAMSH的内在抗生素活性和部分正电荷可能增强了其抗菌作用。织物Eu（表面涂有丁香酚衍生的Ag NPs，[有电子邮件保护]）和织物FQPEG（表面有PEG-氟喹诺酮衍生物包埋的Ag NPs，有[电子邮件保护]）对金黄色葡萄球菌和铜绿假单胞菌均显示出抗菌活性。株。这些涂覆的抗菌棉织物可应用于不同的医用纺织品。
• RADL, STANISLAV;KOVAROVA, LENKA;HOLUBEK, JIRI, COLLECT. CZECHOSL. CHEM. COMMUN., 56,(1991) N, C. 439-448
  作者：RADL, STANISLAV、KOVAROVA, LENKA、HOLUBEK, JIRI

  DOI：——

  日期：——
• Anchoring CuO nanoparticle on nitrogen-doped reduced graphene oxide as nanocatalyst for the synthesis of 5-substituted-1H-tetrazole and 1,2,3- triazole derivatives
  作者：Alka Singh、Alka Agarwal

  DOI：10.1016/j.mcat.2023.113377

  日期：2023.8
• Synthesis and in vitro antiplasmodial activities of fluoroquinolone analogs
  作者：Sandeep K. Dixit、Nidhi Mishra、Manish Sharma、Shailja Singh、Alka Agarwal、Satish K. Awasthi、V.K. Bhasin

  DOI：10.1016/j.ejmech.2012.02.006

  日期：2012.5

  Fluoroquinolone analogs were synthesized by simple alkylation followed by click chemistry and evaluated for their antimalarial in vitro against chloroquine sensitive strain of Plasmodium falciparum while ciprofloxacin was used as standard. Our results showed that the compound 12 was found most active with IC50 value of 1.33 mu g/mL while ciprofloxacin showed IC50 = 8.81 mu g/mL. Therefore, screening of either known or unknown quinolone/fluoroquinolone analogs are worthwhile to find more potent antimalarial drugs which might prove useful in the treatment of mild or severe malaria in human either alone or in combination with existing antimalarial drugs. (C) 2012 Elsevier Masson SAS. All rights reserved.