Synthesis, Spectral Characterization, Molecular Docking Studies, and Biological Evaluation of Pyranoquinolinyl Acrylic Acid (PQAA) Diastereomers as Antibacterial Agents Promoted by Indium (III) Triflate in 1-Butyl-3-Methylimidazolium Tetrafluoroborate Ionic Liquid

IF 0.7 4区化学 Q4 CHEMISTRY, ORGANIC Letters in Organic Chemistry Pub Date : 2024-07-29 DOI:10.2174/0115701786333234240725110033

K. venkatapathy, C. J. Magesh

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Abstract

In the present investigation, we report the multistep synthesis of pyranoquinolinyl acrylic acid (PQAA)/furoquinolinyl acrylic acid (FQAA) diastereomers via perkin condensation and reduction, followed by one-pot inverse electron demand Diels-Alder reaction among 2,3 dihydropyran, amine, and aromatic aldehyde mediated by indium (III) triflate in 1-butyl-3-methylimidazolium tetrafluoroborate (In(OTf)3/ [bmim]BF4) at 25.0-27.0oC. The pyranoquinolinyl acrylic acid/furoquinolinyl acrylic acid diastereomers were evaluated for their in vitro antibacterial activity. Molecular docking studies were carried out employing iGEMDOCK software to evaluate the mode of binding between UDP-N-acetylenolpyruvoyl glucosamine reductase and PQAA adducts. All the pyranoquinolinyl/ furoquinolinyl/tetrahydro-cyclopentaquinolinyl acrylic acid (PQAA/FQAA/CPQAA) diastereomers were thoroughly characterized by NMR, FT-IR, mass spectral, and CHN analysis.

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1-丁基-3-甲基咪唑鎓四氟硼酸盐离子液体中的三氟化铟 (III) 促进吡喃喹啉基丙烯酸 (PQAA) 非对映异构体的合成、光谱表征、分子对接研究和生物学评价

在本研究中，我们报告了通过普金缩合和还原多步合成吡喃喹啉丙烯酸（PQAA）/呋喃喹啉丙烯酸（FQAA）非对映体的过程、然后在 1-丁基-3-甲基咪唑鎓四氟硼酸盐（In(OTf)3/ [bmim]BF4）中以三酸铟（III）为介质，在 25.0-27.0oC。对吡喃喹啉丙烯酸/呋喃喹啉丙烯酸非对映异构体的体外抗菌活性进行了评估。利用 iGEMDOCK 软件进行了分子对接研究，以评估 UDP-N-acetylenolpyruvoyl 葡萄糖胺还原酶与 PQAA 加合物之间的结合模式。所有吡喃喹啉基/呋喃喹啉基/四氢环戊喹啉基丙烯酸（PQAA/FQAA/CPQAA）非对映体都通过核磁共振、傅立叶变换红外光谱、质谱和碳氢化合物分析进行了全面表征。

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来源期刊

Letters in Organic Chemistry 化学-有机化学

CiteScore

1.30

自引率

12.50%

发文量

135

审稿时长

7 months

期刊介绍： Aims & Scope Letters in Organic Chemistry publishes original letters (short articles), research articles, mini-reviews and thematic issues based on mini-reviews and short articles, in all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is to publish quality papers rapidly by taking full advantage of latest technology for both submission and review of the manuscripts. The journal is an essential reading for all organic chemists belonging to both academia and industry.