Design, synthesis and an anti-proliferative activity study of C-14 amide substituted derivatives of dehydroabietic acid

Shi, Qiwen; Meng, Yu; Deng, Shuiguang; Zhang, Ziyuan; Dong, Hewei; Xu, Hongtao; Hou, Wenhua

doi:10.1016/j.phytol.2023.03.012

Phytochemistry Letters

2023

DOI: 10.1016/j.phytol.2023.03.012

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Design, synthesis and an anti-proliferative activity study of C-14 amide substituted derivatives of dehydroabietic acid

Qiwen Shi

Yu Meng

Shuiguang Deng

et al.

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2024

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Novel Abietane Type Sugar Triazole Hybrids and Amides against SARS‐CoV‐2 Spike Glycoprotein and Influenza A Virus

Tretyakova,

Hua,

Smirnova

et al. 2024

Asian J Org Chem

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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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Novel Abietane Type Sugar Triazole Hybrids and Amides against SARS‐CoV‐2 Spike Glycoprotein and Influenza A Virus

Tretyakova,

Hua,

Smirnova

et al. 2024

Asian J Org Chem

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show abstract

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Design, synthesis and an anti-proliferative activity study of C-14 amide substituted derivatives of dehydroabietic acid

Cited by 1 publication

References 31 publications

Novel Abietane Type Sugar Triazole Hybrids and Amides against SARS‐CoV‐2 Spike Glycoprotein and Influenza A Virus

Novel Abietane Type Sugar Triazole Hybrids and Amides against SARS‐CoV‐2 Spike Glycoprotein and Influenza A Virus

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