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      Camphorsulfonic Acid-Mediated One-Pot Tandem Consecutive via the Ugi Four-Component Reaction for the Synthesis of Functionalized Indole and 2-Quinolone Derivatives by Switching Solvents

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          Abstract

          A camphorsulfonic acid-mediated one-pot tandem consecutive approach was developed to synthesize functionalized indole and 2-quinolone derivatives from the Ugi four-component reaction by switching solvents. A reaction of the Ugi adduct in an aprotic solvent undergoes 5- exo-trig cyclization to form an indole ring. In a protic solvent, however, the Ugi adduct undergoes an alkyne-carbonyl metathesis reaction to form a 2-quinolone ring.

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          The combinatorial synthesis of bicyclic privileged structures or privileged substructures.

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            Synthesis and functionalization of indoles through palladium-catalyzed reactions.

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              Quinolones: from antibiotics to autoinducers

              Since quinine was first isolated, animals, plants and microorganisms producing a wide variety of quinolone compounds have been discovered, several of which possess medicinally interesting properties ranging from antiallergenic and anticancer to antimicrobial activities. Over the years, these have served in the development of many synthetic drugs, including the successful fluoroquinolone antibiotics. Pseudomonas aeruginosa and related bacteria produce a number of 2-alkyl-4(1H)-quinolones, some of which exhibit antimicrobial activity. However, quinolones such as the Pseudomonas quinolone signal and 2-heptyl-4-hydroxyquinoline act as quorum-sensing signal molecules, controlling the expression of many virulence genes as a function of cell population density. Here, we review selectively this extensive family of bicyclic compounds, from natural and synthetic antimicrobials to signalling molecules, with a special emphasis on the biology of P. aeruginosa. In particular, we review their nomenclature and biochemistry, their multiple properties as membrane-interacting compounds, inhibitors of the cytochrome bc 1 complex and iron chelators, as well as the regulation of their biosynthesis and their integration into the intricate quorum-sensing regulatory networks governing virulence and secondary metabolite gene expression.
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                Author and article information

                Journal
                ACS Omega
                ACS Omega
                ao
                acsodf
                ACS Omega
                American Chemical Society
                2470-1343
                10 February 2022
                22 February 2022
                : 7
                : 7
                : 5713-5729
                Affiliations
                []Department of Chemistry, National Dong Hwa University , Shoufeng, Hualien 974301, Taiwan
                []Department of Nursing, Tzu Chi University of Science and Technology , Hualien 970302, Taiwan
                [§ ]Instrumentation Center, College of Science, National Taiwan University , Taipei 10617, Taiwan
                Author notes
                Author information
                https://orcid.org/0000-0002-9904-1085
                Article
                10.1021/acsomega.1c05460
                8867550
                4eb64966-88d3-4b05-8342-7a5edee366da
                © 2022 The Authors. Published by American Chemical Society

                Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works ( https://creativecommons.org/licenses/by-nc-nd/4.0/).

                History
                : 01 October 2021
                : 28 January 2022
                Funding
                Funded by: Ministry of Science and Technology, Taiwan, doi 10.13039/501100004663;
                Award ID: MOST 108-2113-M-277-001
                Categories
                Article
                Custom metadata
                ao1c05460
                ao1c05460

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