ethyl 4-oxo-1-(prop-2-yn-1-yl)-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate | 1471177-89-5

• 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 4-oxo-1-(prop-2-yn-1-yl)-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate
• 英文别名: Ethyl 4-oxo-1-prop-2-ynyl-7-(trifluoromethyl)quinoline-3-carboxylate；ethyl 4-oxo-1-prop-2-ynyl-7-(trifluoromethyl)quinoline-3-carboxylate
• CAS: 1471177-89-5
• 化学式: C₁₆H₁₂F₃NO₃
• 分子量: 323.271
• InChiKey: NRQXMXZGXTUUQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 4-oxo-1-(prop-2-yn-1-yl)-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate 在 肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以95%的产率得到4-oxo-1-(prop-2-yn-1-yl)-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carbohydrazide
  参考文献：
  名称：

  Design and regioselective synthesis of trifluoromethylquinolone derivatives as potent antimicrobial agents

  摘要：

  Three series of new trifluoromethyl substituted quinolone derivatives were synthesized (4a-f, 6a-f and 8a-f) from corresponding substituted anilines by multi-step reactions. The regioselective alkylation with different alkyl halides were carried out by approaching two different routes to get the final products in good yield. Newly synthesized compounds were characterized by spectral study and also by C, H, N analyses. Three dimensional structure of 2b and 4b were also confirmed by single crystal X-ray studies. The final compounds (4a-f, 6a-f and 8a-f) were screened for their in-vitro antibacterial and antifungal activity by well plate method (zone of inhibition). The results revealed that, compounds 4a, 6b, 6c and 8e showed significant antibacterial activity as compared to the standard drug Ciprofloxacin. The compound 8a was found to be a potent antifungal agent. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.021
• 作为产物：
  描述：

  二乙基2-[[[3-(三氟甲基)苯基]氨基]亚甲基]丙二酸酯 以 二苯醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 ethyl 4-oxo-1-(prop-2-yn-1-yl)-7-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  羟基三萜酸和氟喹诺酮类新型抗菌和抗生物膜三唑缀合物的设计、半合成和分子对接

  摘要：

  以橄榄果渣 ( Olea europaea L.) 的天然产物分离五环三萜酸为原料，设计并半合成了一系列具有有效抗菌和抗生物膜活性的山楂酸 (MA) 和齐墩果酸 (OA) 类似物。这些缀合物是通过铜催化的叠氮化物-炔环加成 (CuAAC) 的最后一步合成的，在炔丙基化喹诺酮/氟喹诺酮 (QN/FQNs) 和 MA/OA 叠氮化物之间进行，以总体优异的收率获得新的三唑衍生物。后者的杂交体在体外筛选其对两种革兰氏阳性菌（金黄色葡萄球菌和粪肠球菌）和两种革兰氏阴性菌（金黄色葡萄球菌和粪肠球菌）的抗菌和抗生物膜活性。大肠杆菌和铜绿假单胞菌）。结果表明，一些山楂酸衍生物对所有测试菌株均表现出显着的活性，其 MIC 值在 3.25–30 μg mL -1范围内。此外，评估的化合物具有中度至显着的抗生物膜活性，对金黄色葡萄球菌生物膜形成的抑制百分比高达 68.75% 。使用合成化合物抗菌活性对接研究的分

  DOI：

  10.1039/d3nj02922k

文献信息

• Design and regioselective synthesis of trifluoromethylquinolone derivatives as potent antimicrobial agents
  作者：B. Garudachari、Arun M. Isloor、M.N. Satyanarayana、Hoong-Kun Fun、N. Pavithra、Ananda Kulal

  DOI：10.1016/j.ejmech.2013.07.021

  日期：2013.10

  Three series of new trifluoromethyl substituted quinolone derivatives were synthesized (4a-f, 6a-f and 8a-f) from corresponding substituted anilines by multi-step reactions. The regioselective alkylation with different alkyl halides were carried out by approaching two different routes to get the final products in good yield. Newly synthesized compounds were characterized by spectral study and also by C, H, N analyses. Three dimensional structure of 2b and 4b were also confirmed by single crystal X-ray studies. The final compounds (4a-f, 6a-f and 8a-f) were screened for their in-vitro antibacterial and antifungal activity by well plate method (zone of inhibition). The results revealed that, compounds 4a, 6b, 6c and 8e showed significant antibacterial activity as compared to the standard drug Ciprofloxacin. The compound 8a was found to be a potent antifungal agent. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Design, semi-synthesis and molecular docking of new antibacterial and antibiofilm triazole conjugates from hydroxy-triterpene acids and fluoroquinolones
  作者：Besma Boulila、Mabrouk Horchani、Raphael Duval、Mohamed Othman、Adam Daïch、Hichem Ben Jannet、Anis Romdhane、Ata Martin Lawson

  DOI：10.1039/d3nj02922k

  日期：——

  from isolated pentacyclic triterpene acids as natural products from olive pomace (Olea europaea L.). These conjugates were synthesized via a last step of Cu-catalyzed azide–alkyne cycloaddition (CuAAC) between propargylated quinolone/fluoroquinolones (QN/FQNs) and MA/OA azides to achieve new triazole derivatives in overall excellent yields. The latter hybrids were screened in vitro for their antibacterial

  以橄榄果渣 ( Olea europaea L.) 的天然产物分离五环三萜酸为原料，设计并半合成了一系列具有有效抗菌和抗生物膜活性的山楂酸 (MA) 和齐墩果酸 (OA) 类似物。这些缀合物是通过铜催化的叠氮化物-炔环加成 (CuAAC) 的最后一步合成的，在炔丙基化喹诺酮/氟喹诺酮 (QN/FQNs) 和 MA/OA 叠氮化物之间进行，以总体优异的收率获得新的三唑衍生物。后者的杂交体在体外筛选其对两种革兰氏阳性菌（金黄色葡萄球菌和粪肠球菌）和两种革兰氏阴性菌（金黄色葡萄球菌和粪肠球菌）的抗菌和抗生物膜活性。大肠杆菌和铜绿假单胞菌）。结果表明，一些山楂酸衍生物对所有测试菌株均表现出显着的活性，其 MIC 值在 3.25–30 μg mL -1范围内。此外，评估的化合物具有中度至显着的抗生物膜活性，对金黄色葡萄球菌生物膜形成的抑制百分比高达 68.75% 。使用合成化合物抗菌活性对接研究的分