title: Multicomponent Petasis-borono Mannich Preparation of Alkylaminophenols and Antimicrobial Activity Studies.
abstract: In this work we report the antibacterial activity of alkylaminophenols. A series of such compounds was prepared by a multicomponent Petasis-borono Mannich reaction starting from salicylaldehyde and its derivatives. The obtained compounds were tested against a large panel of microorganisms, Gram-positive and Gram-negative bacteria, and a yeast. Among the several tertiary amine derivatives tested, indoline-derived aminophenols containing a nitro group at the para-phenol position showed considerable activity against bacteria tested with minimal inhibitory concentrations as low as 1.36 μm against Staphyloccocus aureus and Mycobacterium smegmatis. Cytotoxicity of the new para-nitrophenol derivatives was observed only at concentrations much higher than those required for antibacterial activity.
authors.affiliation: Center for Research in Biosciences & Health Technologies (CBIOS), Universidade Lusófona de Humanidades e Tecnologias, 1749-024, Lisboa, Portugal.
authors.forename: Íris
authors.initials: Í
authors.lastname: Neto
authors.affiliation: Center for Research in Biosciences & Health Technologies (CBIOS), Universidade Lusófona de Humanidades e Tecnologias, 1749-024, Lisboa, Portugal.
authors.forename: Joana
authors.initials: J
authors.lastname: Andrade
authors.affiliation: Center for Research in Biosciences & Health Technologies (CBIOS), Universidade Lusófona de Humanidades e Tecnologias, 1749-024, Lisboa, Portugal.
authors.forename: A S
authors.initials: AS
authors.lastname: Fernandes
authors.affiliation: Center for Research in Biosciences & Health Technologies (CBIOS), Universidade Lusófona de Humanidades e Tecnologias, 1749-024, Lisboa, Portugal.
authors.forename: Catarina
authors.initials: C
authors.lastname: Pinto Reis
authors.affiliation: Department of Chemistry and Bioengineering, Tampere University of Technology, Korkeakoulunkatu 8, 33101, Tampere, Finland.
authors.forename: Jagadish K
authors.initials: JK
authors.lastname: Salunke
authors.affiliation: Department of Chemistry and Bioengineering, Tampere University of Technology, Korkeakoulunkatu 8, 33101, Tampere, Finland.
authors.forename: Arri
authors.identifier: 0000-0002-5945-9671
authors.initials: A
authors.lastname: Priimagi
authors.affiliation: Department of Chemistry and Bioengineering, Tampere University of Technology, Korkeakoulunkatu 8, 33101, Tampere, Finland. nuno.rafaelcandeias@tut.fi.
authors.forename: Nuno R
authors.identifier: 0000-0003-2414-9064
authors.initials: NR
authors.lastname: Candeias
authors.affiliation: Center for Research in Biosciences & Health Technologies (CBIOS), Universidade Lusófona de Humanidades e Tecnologias, 1749-024, Lisboa, Portugal. patricia.rijo@ulusofona.pt.|Instituto de Investigação do Medicamento (iMed.ULisboa), Faculdade de Farmácia, Universidade de Lisboa, 1649-003, Lisboa, Portugal. patricia.rijo@ulusofona.pt.
authors.forename: Patrícia
authors.identifier: 0000-0001-7992-8343
authors.initials: P
authors.lastname: Rijo
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001596:Benzylamines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D020102:Mycobacterium smegmatis / Q000187:drug effects*; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D001596:Benzylamines; D010636:Phenols
keywords: alkylaminophenols; antibacterial activity; multicomponent reactions; structure-activity relationships