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Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4- N -arylamine-1-butenes and related compounds with inhibitory activities on β(1–3) glucan and chitin synthases Urbina, Juan M García Cortés, Juan Carlos Palma, Alirio López, Silvia N Zacchino, Susana A Enriz, Ricardo D Ribas Elcorobarrutia, Juan Carlos Kouznetzov, Vladimir V Agentes antifúngicos 4-aril- o 4-alquil-N-arilamina-1-butenos Células de los hongos Antifungal agents Inhibitors of the fungal cell wall 2414 Microbiología 2407 Biología Celular 2302.21 Biología Molecular 2302 Bioquímica [EN]As part of our project devoted to the search for antifungal agents, which act via a selective mode of action, we synthesized a series of new 4-aryl- or 4-alkyl-N-arylamine-1-butenes and transformed some of them into 2-substituted 4-methyl-tetrahydroquinolines and quinolines by using a novel three-step synthesis. Results obtained in agar dilution assays have shown that 4-aryl homoallylamines not possessing halogen in their structures, tetrahydroquinolines and quinolines, display a range of antifungal properties in particular against Epidermophyton floccosum and Microsporum canis. Regarding the mode of action, all active compounds showed in vitro inhibitory activities against β(1–3) glucan-synthase and mainly against chitin-synthase. These enzymes catalyze the synthesis of β(1–3) glucan and chitin, respectively, major polymers of the fungal cell wall. Since fungal but not mammalian cells are encased in a cell wall, its inhibition may represent a useful mode of action for these antifungal compounds. Colciencias (Colombia), CONICET (Argentina), Universidad Nacional de Rosario (Argentina), CICYT (España), Iberoamerican Program of Science and Technology for the Development (CYTED) 2024-04-08T11:14:21Z 2024-04-08T11:14:21Z 2000 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Juan M Urbina, Juan C.G Cortés, Alirio Palma, Silvia N López, Susana A Zacchino, Ricardo D Enriz, Juan C Ribas, Vladimir V Kouznetzov, Inhibitors of the fungal cell wall. Synthesis of 4-aryl-4-N-arylamine-1-butenes and related compounds with inhibitory activities on β(1–3) glucan and chitin synthases, Bioorganic & Medicinal Chemistry, Volume 8, Issue 4, 2000, Pages 691-698 0968-0896 http://hdl.handle.net/10366/157202 10.1016/s0968-0896(00)00003-1 10819157 eng https://doi.org/10.1016/s0968-0896(00)00003-1 CYCYT/BIO98-0814-C02-01 Colciencias/115-05-353-96 CONICET/PEI 239/97 Universidad Nacional de Rosario (Argentina)/Project B050 CC0 1.0 Universal http://creativecommons.org/publicdomain/zero/1.0/ info:eu-repo/semantics/openAccess Elsevier https://gredos.usal.es/bitstream/10366/157202/5/2000_Inhibitors%20of%20the%20fungal%20cell%20wall.pdf.jpg Hispana TEXT http://creativecommons.org/publicdomain/zero/1.0/ Gredos. Repositorio Documental de la Universidad de Salamanca http://hdl.handle.net/10366/157202