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- W2981388093 abstract "The design and synthesis of a quality compound library containing a small number of skeletally diverse scaffolds, whose members rapidly deliver new chemical probes active against multiple phenotypes, is paramount in drug discovery. In this context, an efficient one-pot strategy for the synthesis of a mini library of sp3-enriched hexahydropyrido[2′,1′:2,3]imidazo[1,5-a]quinolinium and hexahydrothiazolo[2′,3′:2,3]imidazo[1,5-a]quinolinium architectures, is described. This new one-pot method features a combination of Sc(OTf)3-catalyzed [4 + 1]-cycloaddition with aza-Michael addition reactions. The cascade results in a rapid and diastereoselective formation of these scaffolds via desymmetrization of the oxidative dearomatization products of phenols. Phenotypic screening of the mini library against multiple drug-resistant bacteria and a panel of cancer cell lines identified potential antibacterial and anticancer lead drug candidates. Further investigation of the anticancer leads, indicated by their activity as tubulin-polymerization inhibitors, represents a promising approach for cancer therapy." @default.
- W2981388093 created "2019-11-01" @default.
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- W2981388093 date "2019-10-21" @default.
- W2981388093 modified "2023-10-14" @default.
- W2981388093 title "Sequencing [4 + 1]-Cycloaddition and Aza-Michael Addition Reactions: A Diastereoselective Cascade for the Rapid Access of Pyrido[2′,1′:2,3]/Thiazolo[2′,3′:2,3]imidazo[1,5-<i>a</i>]quinolone Scaffolds as Potential Antibacterial and Anticancer Motifs" @default.
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- W2981388093 doi "https://doi.org/10.1021/acs.joc.9b01919" @default.
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