The semi-synthesis of novel andrographolide analogues and anti-influenza virus activity evaluation of their derivatives

Bioorganic & Medicinal Chemistry Letters
Lei YuanLixia Chen

Abstract

Two novel andrographolide analogues with the structural motif of Δ(8,17)-alkene exo-to-endo isomerization, AI78 and AI89, were semi-synthesized firstly. Two series of derivatives were designed and synthesized based on the synthetic pathway (including series I: olefin isomerizing to endocyclic Δ(8,9) and series II: olefin isomerizing to endocyclic Δ(7,8)). The anti-influenza virus activity in vitro for all derivatives was evaluated. Among the compounds synthesized, compound 38 with benzyl amino group showed the greatest potency against H3N2 and was approximately 1.5-fold more potent than that of Lianbizhi, andrographolide analogue used clinically in China. Adamantyl derivative, 43, presented the lowest toxicity, with a higher TC50 and TI values than Lianbizhi. The structure-activity relationships studies of the synthetic analogues indicated that the endocyclic Δ(7,8)-double bond is preferable for anti-viral effect. Furthermore, the introduction of the fatty amino attached to the rigid skeleton at C-17 is beneficial for activity.

References

May 12, 2009·Trends in Pharmacological Sciences·Robert M Krug, James M Aramini
Feb 15, 2012·Expert Opinion on Therapeutic Patents·Chantana Aromdee

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Citations

Aug 30, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jinhua LiLinfang Huang
Nov 30, 2016·Archives of Virology·Swati GuptaLilly Ganju
May 1, 2021·Phytotherapy Research : PTR·Ashwini Khanderao Jadhav, Sankunny Mohan Karuppayil
Apr 30, 2020·Mini Reviews in Medicinal Chemistry·Meng HaoHui Xu
Jul 28, 2021·European Journal of Medicinal Chemistry·Hang ZhangHaiwei Xu
Aug 27, 2021·International Immunopharmacology·Swati GuptaS B Singh
Nov 28, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Archana MishraBakht Ramin Shah

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