4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide | 873942-91-7

• 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: 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide
• 英文别名: 4-oxo-8-(trifluoromethyl)-1H-quinoline-3-carbohydrazide
• CAS: 873942-91-7
• 化学式: C₁₁H₈F₃N₃O₂
• 分子量: 271.199
• InChiKey: OETNJGVZOBKJOR-UHFFFAOYSA-N

物化性质

• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  84.2
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-二氢苯并呋喃-5-甲醛 、 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以91%的产率得到
  参考文献：
  名称：

  Design, synthesis and docking studies of new quinoline-3-carbohydrazide derivatives as antitubercular agents

  摘要：

  Three new series of 4-hydroxy-8-trifluoromethyl-quinoline derivatives were synthesized through multi step reactions. All the newly synthesized compounds were characterized by spectral and elemental analyses. The structure of 5j was evidenced by X-ray crystallographic study. The newly synthesized title compounds were evaluated for their antimicrobial activities including antimycobacterial activity. Amongst the tested compounds, 5b, 5e, 5h, 5j, 6c and 7c displayed promising antimicrobial activity. The mode of action of these active compounds was carried out by docking of receptor enoyl-ACP reductase with newly synthesized candidate ligands, 5b, 5e, 5h, 5j and 6c. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.033
• 作为产物：
  描述：

  邻氨基三氟甲苯 在 联苯 、 hydrazine hydrate 作用下， 生成 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide
  参考文献：
  名称：

  1,3-噻嗪南-4-酮衍生物的一些新喹啉的合成，鉴定及体外生物学评价

  摘要：

  本研究描述了两个新系列的3-羟基-N-（4-氧代-2-苯基-1,3-噻嗪基-3-基）-8-（三氟甲基）喹啉-2-羧酰胺衍生物的合成（4a – j）和3-（（7-氯喹啉-4-基氨基）甲基）-2-苯基-1,3-噻嗪南-4-酮衍生物（5a – 7j）。通过一锅三组分环缩合反应以中等至良好的收率合成所有化合物。通过FT-IR，1 H，13 C NMR和元素分析对新合成的化合物进行表征。筛选化合物对一组致病细菌菌株的体外抗菌活性，对这些细菌的抗结核活性。结核分枝杆菌H 37 Rv以及它们对恶性疟原虫的体外抗疟活性。在合成的化合物中，其中两个（4f和5f）以15.6μg/ mL的浓度显示了对破伤风梭菌的出色抗菌活性。与一线药物相比，其中一些药物显示出优异的抗结核（4f和5f）和良好的抗疟疾（4f，5f和6f）活性。

  DOI：

  10.1016/j.bmcl.2016.06.038

文献信息

• Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety
  作者：Sumesh Eswaran、Airody Vasudeva Adhikari、N. Suchetha Shetty

  DOI：10.1016/j.ejmech.2009.06.031

  日期：2009.11

  A new class of quirroline derivatives containing 1,2,4-triazole moiety were synthesized from derivatives of 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide 4 through multi-step reactions. The compound 4, on treatment with substituted Isothiocyanates yielded quinoline-thiosemicarbazides 5a-c, which were conveniently cyclized to (5-mercapto-4H-triazol-3-yl)-quinolin-4-ols 6a-c in basic medium. These intermediates were then transformed to their respective chloro derivatives 7a-c by treatment with phosphorus oxychloride, which on further reaction with different biologically active rare amines yielded the target compounds 8a-g, 9a-h and 10a-h in good yield. The ultimate step, involving nucleophilic substitution reaction was achieved by microwave-induced technique, which has reduced the reaction time drastically as well as improved the yield when compared to conventional heating. The newly synthesized final compounds were evaluated for their in vitro antibacterial and antifungal activities against four strains each. Preliminary results indicated that most of the compounds demonstrated very good antimicrobial activity, comparable to the first line standard drugs. The most effective compounds have exhibited activity at MIC of 6.25 mu g/mL. (C) 2009 Elsevier Masson SAS. All rights reserved.
• 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, synthesis and docking studies of new quinoline-3-carbohydrazide derivatives as antitubercular agents
  作者：K.D. Thomas、Airody Vasudeva Adhikari、Sandeep Telkar、Imran H. Chowdhury、Riaz Mahmood、Nishith K. Pal、Guru Row、E. Sumesh

  DOI：10.1016/j.ejmech.2011.07.033

  日期：2011.11

  Three new series of 4-hydroxy-8-trifluoromethyl-quinoline derivatives were synthesized through multi step reactions. All the newly synthesized compounds were characterized by spectral and elemental analyses. The structure of 5j was evidenced by X-ray crystallographic study. The newly synthesized title compounds were evaluated for their antimicrobial activities including antimycobacterial activity. Amongst the tested compounds, 5b, 5e, 5h, 5j, 6c and 7c displayed promising antimicrobial activity. The mode of action of these active compounds was carried out by docking of receptor enoyl-ACP reductase with newly synthesized candidate ligands, 5b, 5e, 5h, 5j and 6c. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis, identification and in vitro biological evaluation of some novel quinoline incorporated 1,3-thiazinan-4-one derivatives
  作者：S. Umamatheswari、C. Sankar

  DOI：10.1016/j.bmcl.2016.06.038

  日期：2017.2

  The present study describes the synthesis of two new series of 3-hydroxy-N-(4-oxo-2-phenyl-1,3-thiazinan-3-yl)-8-(trifluoromethyl)quinoline-2-carboxamide derivatives (4a–j) and 3-((7-chloroquinolin-4-ylamino)methyl)-2-phenyl-1,3-thiazinan-4-one derivatives (5a–7j). All the compounds were synthesized in moderate to good yield by one-pot three component cyclo-condensation reaction. The newly synthesized

  本研究描述了两个新系列的3-羟基-N-（4-氧代-2-苯基-1,3-噻嗪基-3-基）-8-（三氟甲基）喹啉-2-羧酰胺衍生物的合成（4a – j）和3-（（7-氯喹啉-4-基氨基）甲基）-2-苯基-1,3-噻嗪南-4-酮衍生物（5a – 7j）。通过一锅三组分环缩合反应以中等至良好的收率合成所有化合物。通过FT-IR，1 H，13 C NMR和元素分析对新合成的化合物进行表征。筛选化合物对一组致病细菌菌株的体外抗菌活性，对这些细菌的抗结核活性。结核分枝杆菌H 37 Rv以及它们对恶性疟原虫的体外抗疟活性。在合成的化合物中，其中两个（4f和5f）以15.6μg/ mL的浓度显示了对破伤风梭菌的出色抗菌活性。与一线药物相比，其中一些药物显示出优异的抗结核（4f和5f）和良好的抗疟疾（4f，5f和6f）活性。