{"title":"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","authors":"K. venkatapathy, C. J. Magesh","doi":"10.2174/0115701786333234240725110033","DOIUrl":null,"url":null,"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.","PeriodicalId":18116,"journal":{"name":"Letters in Organic Chemistry","volume":"11 1","pages":""},"PeriodicalIF":0.7000,"publicationDate":"2024-07-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"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\",\"authors\":\"K. venkatapathy, C. J. Magesh\",\"doi\":\"10.2174/0115701786333234240725110033\",\"DOIUrl\":null,\"url\":null,\"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.\",\"PeriodicalId\":18116,\"journal\":{\"name\":\"Letters in Organic Chemistry\",\"volume\":\"11 1\",\"pages\":\"\"},\"PeriodicalIF\":0.7000,\"publicationDate\":\"2024-07-29\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Letters in Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.2174/0115701786333234240725110033\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Letters in Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.2174/0115701786333234240725110033","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
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
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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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.
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