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Molecules 2011, 16, 4786-4806; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis and In Vitro Antiproliferative Activity of Novel Androst-5-ene Triazolyl and Tetrazolyl Derivatives Zalán Kádár 1,*, Dóra Kovács 1, Éva Frank 1, Gyula Schneider 1, Judit Huber 2, István Zupkó 2, Tibor Bartók 3,4 and János Wölfling 1,* 1 Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary 2 Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary 3 Faculty of Engineering, University of Szeged, Moszkvai krt. 5-7, H-6725 Szeged, Hungary 4 Fumizol Ltd., Moszkvai krt. 5-7, H-6725 Szeged, Hungary * Authors to whom correspondence should be addressed; E-Mails: wolfling@chem.u-szeged.hu (J.W.); zkadar@chem.u-szeged.hu (Z.K.); Tel.: +36-62-544-200; Fax: +36-62-544-200. Received: 12 May 2011; in revised form: 2 June 2011 / Accepted: 6 June 2011 / Published: 9 June 2011 Abstract: A straightforward and reliable method for the regioselective synthesis of steroidal 1,4-disubstituted triazoles and 1,5-disubstituted tetrazoles via copper(I)-catalyzed cycloadditions is reported. Heterocycle moieties were efficiently introduced onto the starting azide compound 3β-acetoxy-16β-azidomethylandrost-5-en-17β-ol through use of the “click” chemistry approach. The antiproliferative activities of the newly-synthesized triazoles were determined in vitro on three human gynecological