Background: Anthraquinone derivatives, frequently occurring motifs in many various
natural compounds, have attracted a great deal of interest as compounds with a wide spectrum of
Introduction: The hybrid pharmacophore approach has become an object of considerable interest
due to the incorporation of a five- or six-membered heterocyclic rings in the structure of various
natural compounds, especially anthraquinone derivatives.
Methods: A series of polyfunctionalized anthraquinonehydrazones have been synthesized via the
azo-coupling reaction between anthraquinone-based triazenes and methylene active compounds. The
structures of synthesized compounds were confirmed by spectral data. Some of the synthesized
compounds were screened for their in vitro anticancer activity according to US NCI protocols. The
screening of antimicrobial and antifungal activities against Candida albicans and Lactobacillus sp.
was carried out. The synthesized compounds were evaluated for their antioxidant (DPPH free radical
scavenging assay) and herbicidal activity.
Results: The synthesized 1-[N'-(5-oxo-2-thioxoimidazolidin-4-ylidene)-hydrazino]-anthraquinone
1.5 displayed a high level of antimitotic activity against tested human tumor cells with mean
GI50/TGI values 4.06/78.52μM. The screening of antimicrobial and antifungal activities led to the
identification of 1.8 and 1.9 with a moderate effect on Candida albicans and Lactobacillus sp. Antioxidant
activity evaluation allowed the identification of 1-[N'-(3-methyl-5-oxo-1-phenyl-1,5-
dihydropyrazol-4-ylidene)-hydrazino]-anthraquinone 1.8 with an IC50 value of 3.715 mM. The herbicidal
activity screening led to compound identification 1.8 with growth inhibition of Agrostis stolonifera
at 25 %.
Conclusion: The obtained anthraquinonehydrazones constitute an interesting template for the design
of new synthetic agents with polypharmacological activities.
Keywords: Anthraquinones, hybrid pharmacophore approach, anticancer activity, antioxidant activity, antimicrobial activity,
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