Regional Issue "Organic Chemistry in Argentina" ARKIVOC 2011 (vii) 149-161 Page 149 © ARKAT-USA, Inc. Synthesis and antifungal activity of N-aryl-N-benzylamines and of their homoallyl analogues Francisco M. Garibotto, a,b Maximiliano A. Sortino, a,c Vladimir V. Kouznetsov, d Ricardo D. Enriz, b,c and Susana A. Zacchino a * a Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario. Suipacha 531, 2000-Rosario, Argentina b Química General, Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luis, Chacabuco 915, 5700-San Luis, Argentina c IMIBIO-CONICET, Universidad Nacional de San Luis, Chacabuco 915, 5700-San Luis, Argentina d Laboratorio de Química Orgánica y Biomolecular, Escuela de Química, Universidad Industrial de Santander, A.A. 678 Bucaramanga, Colombia E-mail: szaabgil@citynet.net.ar In honour of Professors Rita H. Rossi, Julio C. Podestá, Manuel González Sierra and Oscar S. Giordano, recognising their contributions to the development of Organic Chemistry in Argentina Abstract Ten N-aryl-N-benzylamines were synthesized and evaluated for their antifungal activity, which was compared with their homoallylamine analogues that possessed an allyl group in the carbon next to the nitrogen atom. Results indicated that the absence of the allyl group caused an enhancement of the antifungal activity which could be correlated with the flexibility of the alkyl chain between both aromatic groups. DFT calculations supported these differences in activity. Keywords: N-arylamines, Homoallylamines, Antifungal, DFT calculations Introduction Among the different microbes that affect the quality of life, fungi have an enormous impact on morbidity and mortality, especially among the immunocompromised hosts, since they have emerged over the past two decades as major causes of human infections. 1 They produce serious invasive mycoses in individuals submitted to organ transplantations or antineoplasic chemotherapy, those suffering the acquired immunodeficiency syndrome (AIDS), extremely