An easy microwave-assisted synthesis of C8-alkynyl adenine pyranonucleosides as novel cytotoxic antitumor agents

Athina Dimopoulou; Stella Manta; Vanessa Parmenopoulou; Nikolaos Kollatos; Ourania Christidou; Virginia V Triantakonstanti; Dominique Schols; Dimitri Komiotis

doi:10.3389/fchem.2015.00021

An easy microwave-assisted synthesis of C8-alkynyl adenine pyranonucleosides as novel cytotoxic antitumor agents

Front Chem. 2015 Mar 23:3:21. doi: 10.3389/fchem.2015.00021. eCollection 2015.

Authors

Athina Dimopoulou¹, Stella Manta¹, Vanessa Parmenopoulou¹, Nikolaos Kollatos¹, Ourania Christidou¹, Virginia V Triantakonstanti², Dominique Schols³, Dimitri Komiotis¹

Affiliations

¹ Laboratory of Bioorganic Chemistry, Department of Biochemistry and Biotechnology, University of Thessaly Larissa, Greece.
² Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki Thessaloniki, Greece.
³ Department of Microbiology and Immunology, Rega Institute for Medical Research, KU Leuven Leuven, Belgium.

Abstract

We describe the synthesis of C8-alkynyl adenine pyranonucleosides 4, 5, and 8-phenylethynyl-adenine (II), via Sonogashira cross-coupling reaction under microwave irradiation. Compounds 4e and II were less cytostatic than 5-fluorouracil (almost an order of magnitude) against murine leukemia (L1210) and human cervix carcinoma (HeLa) cells, while the same compounds proved to be more active than 5-fluorouracil against human lymphocyte (CEM) cells.

Keywords: 8-bromoadenine; N6-benzoyladenine pyranonucleosides; Sonogashira coupling reaction; cytotoxic activity; microwave irradiation.