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- W4379378499 abstract "Studies suggest that the 1′β–CN moiety in remdesivir sterically clashes with the Ser861 residue of the RNA-dependent-RNA polymerase (RdRp), causing a delayed chain termination in the RNA replication process. Replacing C1′β–CN with 5-membered heterocycles such as tetrazoles, oxadiazoles, and triazoles can augment the inhibitory activity and pharmacokinetic profile of C-nucleotides. Synthesis of tetrazole-, triazole-, and oxadiazole-integrated C1′ analogues of remdesivir was attempted using general synthetic routes. The final compounds 26, 28, and 29 did not inhibit viral replication; however, the synthetic intermediates, i.e., 27 and 50, exhibited an IC90 = 14.1 μM each. The trifluoromethyl-substituted 1,2,4-oxadiazole 59 showed an IC90 of 33.5 μM. This work adds to the growing evidence of the beneficial medicinal impact of C1,1′-disubstituted C-nucleotides." @default.
- W4379378499 created "2023-06-06" @default.
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- W4379378499 date "2023-06-05" @default.
- W4379378499 modified "2023-10-03" @default.
- W4379378499 title "Multistep Synthesis of Analogues of Remdesivir: Incorporating Heterocycles at the C-1′ Position" @default.
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- W4379378499 doi "https://doi.org/10.1021/acs.joc.3c00754" @default.
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