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CYTOTOXIC EVALUATION OF ORIGINAL PYRAZOLO[3,4d]THIAZOLES AND PYRAZOLO[3,4-c]PYRAZOLES

NICU-COSMIN OSTACHE 1,2, ARNAUD PARIS 1, MARIE-AUDE HIEBEL 1, ADRIANA- LUMINIȚA FÎNARU 2, RICHARD DANIELLOU 1, FRANCK SUZENET 1, GÉRALD
GUILLAUMET 1*

1Institut de Chimie Organique et Analytique (ICOA), Université d’Orleans UMR CNRS 7311, BP 6759, 45067 Orléans
Cedex 2, France
2 Center of Applied Chemistry and Process Engineering (CAIP), University Vasile Alecsandri of Bacău, 157 Calea Mărăşeşti Street, Bacău, 600115, Romania

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A concise and versatile synthetic strategy for the synthesis of original substituted heterobicycles was developed, relying on the use of aromatic hydrazines in one-pot condensations and Ullmann-type intramolecular cyclization sequences, as well as on chemoselective brominations and palladium-mediated cross-coupling reactions. In this study, the two series of novel heterobicycles were tested for their cytotoxic potential. The compounds were structurally characterized by nuclear magnetic resonance spectrometry (1H NMR and 13C NMR), infrared spectroscopy (IR) and high-resolution mass spectrometry (HRMS). The IC50 values of these compounds on five tumour cell lines (A-549, HS-683, MCF-7, SK-MEL-28 and B16-F1) were obtained by MTT colorimetric assay. Six of the compounds exhibited excellent activity compared to 5-fluorouracil against two of the five cell lines tested, with IC50 values ranging from 0.1 to 10 μM.