Synthesis and biological evaluation of a post-synthetically modified Trp-based diketopiperazine
Barcelona Science Park, Baldiri Reixac 10-12, 08028 Barcelona, Spain; Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10-12, 08028 Barcelona, Spain; Department of Organic Chemistry, Faculty of Chemistry, University of Barcelona, Martí I Franqués 1-11, 08028 Barcelona, Spain; CIBER-BBN, Networking Centre on Bioengineering Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona, Spain; Department of Patology and Experimental Therapeutics, Faculty of Medicine, University of Barcelona, Feixa Llarga s/n, Pavelló de Govern. 08907 L'Hospitalet, Barcelona, Spain; School of Chemistry, University of KwaZulu-Natal, 4001-Durban, South Africa; Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Avda. Joan XXII s.n., 08028 Barcelona, Spain
A series of C2-arylated analogues of the diketopiperazine brevianamide F has been synthesized using a mild Pd-catalyzed CH-activation procedure. Biological evaluation of the new derivatives in different cell lines shows that this modification is responsible for the remarkable change in activity, turning a mild antibiotic and antifungal natural product (brevianamide F) into novel antitumoral compounds. Furthermore, the approach stated represents a new straightforward and versatile methodology with promising applications in peptidomimetics and medicinal chemistry. © 2013 The Royal Society of Chemistry.
antineoplastic agent; brevianamide F derivative; puromycin; unclassified drug; antineoplastic activity; antiproliferative activity; article; arylation; breast adenocarcinoma; cancer cell culture; catalysis; chemical modification; colon adenocarcinoma; controlled study; drug cytotoxicity; drug mechanism; drug potency; drug screening; drug structure; drug synthesis; human; human cell; lung carcinoma; priority journal; stereoisomerism; uterine cervix carcinoma