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Asian Journal of Organic Chemistry

Asian Journal of Organic Chemistry

IF: 2.8
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Novel Abietane type Sugar Triazole Hybrids and Amides against SARS-CoV-2 Spike Glycoprotein and Influenza A Virus

Published:1 September 2024 DOI: 10.1002/ajoc.202400227
Dr. Elena Tretyakova, Dr. Liwen Hua, Anna Smirnova, Prof.?Dr. Oxana Kazakova, Prof.?Dr. Vladimir Zarubaev, Dr. Hongwei Jin, Dr. Huan Xu, Prof.?Dr. Sulong Xiao

Abstract

Abietane type diterpenic (dehydroabietic, 2,3-dihydroquinopimaric and maleopimaric) acids were converted by the acid chloride method into a series of aliphatic and heterocyclic amine spacered conjugates. A number of structurally novel derivatives holding 1,2,3-triazole moieties were designed and synthesized by treating of the propargylated amides and esters with a sugar azides using the Cu(I)-catalyzed click chemistry approach. The synthesized N-containing diterpene derivatives were tested for their potential inhibition of influenza A/PuertoRico/8/34 (H1N1) virus in MDCK cell culture and SARS-CoV-2 pseudovirus in BHK-21-hACE2 cells. Among tested forty-five compounds ten derivatives were the most efficacious against influenza virus A with IC50 0.7–63.4?μM together with high selectivity index SI value from 11 from 94. Dihydroquinopimaric acid N-ethylpiperazine-amide and dehydroabietic acid 1,2,3-triazoles spacered with glucose and lactose showed anti-SARS-CoV-2 pseudovirus activity with EC50 values of 1.79–25.46?μM. Molecular docking and dynamics modeling investigated the binding mode of the lead compounds into the binding pocket of influenza A virus M2 protein and the RBD domain of SARS-CoV-2 spike glycoprotein.

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