Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry

Abstract

Naturally occurring terpenes were combined by click reactions to generate sixteen hybrid molecules. The diterpene imbricatolic acid (IA) containing an azide group was used as starting compound for the synthesis of all the derivatives. The alkyne group in the terpenes cyperenoic acid, dehydroabietinol, carnosic acid γ-lactone, ferruginol, oleanolic acid and aleuritolic acid was obtained by esterification using appropriate alcohols or acids. The hybrid compounds were prepared by combining the IA azide function with the different terpene-alkynes under click chemistry conditions. The cytotoxic activity of the terpene hybrids 1–16 was assessed against Vero cells and tumour cell lines (HEP-2, C6 and Raw 264.7). Compounds 1, 2, 3 and 7 showed cytotoxic activity against the tested cell lines. The antiviral activity of the compounds was evaluated against HSV-1 KOS, Field and B2006 strain. For the pairs of hybrid compounds formed between IA-diterpene (compounds 3–8, except for compound 7), a moderate activity was observed against the three HSV-1 strains with an interesting selectivity index (SI ≥10, SI = CC50/CE50) for some compounds.

An expedient synthesis of novel bis[thienopyridines] linked to arene or heteroarene core as novel hybrid molecules

“…Motivated by these findings and in conjunction with recent interest on molecular hybridization concept as well as on the chemistry of bis-heterocyclic compounds, [26][27][28][29][30][31][32][33][34][35][36][37][38][39] we report herein on the synthesis of novel bis[thienopyridines] linked to arene or heteroarene spacers.…”

Synthesis and Antiproliferative Activity of Novel Heterocyclic Glycyrrhetinic Acid Derivatives

“…Cycloaddition of azides and alkynes, commonly referred to as “click chemistry”, has acquired great interest in the development of novel heterocyclic compounds with varied biological activities [ 30 , 31 , 32 , 33 ]. This efficient and simple process has been successfully used in the synthesis of pentacyclic triterpenoid derivatives with improved anticancer activity [ 34 , 35 , 36 , 37 ].…”

Potential Antiviral Xanthones from a Coastal Saline Soil Fungus Aspergillus iizukae

“…The anti-herpes simplex virus types 1 (HSV-1) and 2 (HSV-2) activity of 1 − 7 on Vero cells were conducted in the same way as described above [ 20 ], and acyclovir (ACV) was applied as the positive control.…”