Title:Synthesis and Biological Activity Evaluation of Polyfunctionalized Anthraquinonehydrazones
VOLUME: 18 ISSUE: 2
Author(s):Andrii Lozynskyi, Serhii Holota, Ihor Yushyn, Oksana Sabadakh, Olexandr Karpenko, Volodymyr Novikov and Roman Lesyk*
Affiliation:Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, Lviv 79010, Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, Lviv 79010, Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, Lviv 79010, Department of Environmental Chemistry and Chemistry Education, Vasyl Stefanyk Precarpathian National University, Halytska 201, Ivano-Frankivsk 76000, Enamine Ltd, 23 Alexandra Matrosova, Kiev 01103, Department of Technology of Biologically Active Substances, Pharmacy and Biotechnology, Lviv Polytechnic National University, Bandery 12, Lviv 79013, Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Pekarska 69, Lviv 79010
Keywords:Anthraquinones, hybrid pharmacophore approach, anticancer activity, antioxidant activity, antimicrobial activity,
herbicidal activity.
Abstract: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
biological activities.
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.
