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European journal of medicinal chemistry v.143, 2018년, pp.1010 - 1020   SCI SCIE
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Hetero-Diels-Alder reactions of novel 3-triazolyl-nitrosoalkenes as an approach to functionalized 1,2,3-triazoles with antibacterial profile

Lopes, Susana M.M. (CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal ) ; Novais, Juliana S. (Universidade Federal Fluminense, PPBI, Instituto de Biologia, Campus Valonguinho, 24210130, Niterói, RJ, Brazil ) ; Costa, Dora C.S. (Universidade Federal Fluminense, Departamento de Química Orgânica, Instituto de Química, Campus do Valonguinho, 24020-150, Niterói, RJ, Brazil ) ; Castro, Helena C. (Universidade Federal Fluminense, PPBI, Instituto de Biologia, Campus Valonguinho, 24210130, Niterói, RJ, Brazil ) ; Figueiredo, Agnes Marie S. (Universidade Federal do Rio de Janeiro, Instituto de Microbiologia Professor Paulo de Góes, Departamento de Microbiologia Médica, Rio de Janeiro, Brazil ) ; Ferreira, Vitor F. (Universidade Federal Fluminense, Departamento de Tecnologia Farmacêutica, Faculdade de Farmácia, Niterói, RJ, 24241-002, Brazil ) ; Pinho e Melo, Teresa M.V.D. (CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal ) ; da Silva, Fernando de Carvalho (Universidade Federal Fluminense, Departamento de Química Orgânica, Instituto de Qu&i ) ;
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    Abstract The generation and reactivity of 3-triazolyl-nitrosoalkenes are reported for the first time. The study showed that hetero-Diels-Alder reaction of these heterodienes is an interesting synthetic strategy to functionalized 1,2,3-triazoles, including 1,2,3-triazolyl-pyrroles, 1,2,3-triazolyl-dipyrromethanes and 1,2,3-triazolyl-indoles. The evaluation of the antibacterial profile against Gram-positive and Gram-negative strains revealed the new 5,5′-diethyldipyrromethane bearing a side chain incorporating a triazole and oxime moieties. The antibacterial profile detected was within the Clinical and Laboratory Standard Institute (CLSI) range and against important Staphylococcus species including Methicillin-resistant strain ( S. aureus ATCC 25923, S. epidermidis ATCC 12228 and S. simulans ATCC 27851 and MRSA). Interestingly, this new 1,2,3-triazole presented hemocompatibility and low in silico toxicity profile similar to antibiotics current in use. It also has an usual antibiofilm activity against MRSA, which reinforced its potential as a new antibacterial prototype. Highlights The generation and reactivity of new 3-triazolyl-nitrosoalkenes are reported. 1,2,3-triazoles linked to pyrroles, dipyrromethanes and indoles were synthesized. 1,2,3-triazoles have been evaluated against bacteria gram-positive and gram-negative. 1,2,3-triazoles linked to dipyrromethane presented promising antibacterial profile. Graphical abstract [DISPLAY OMISSION]


  • 주제어

    1,2,3-Triazoles .   Pyrrole .   Diels-Alder reaction .   α-bromooximes .   Antibacterial.  

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