UMYMFOR 05516
UNIDAD DE MICROANALISIS Y METODOS FISICOS EN QUIMICA ORGANICA
Unidad Ejecutora - UE
congresos y reuniones científicas
Título:
3-(Difluoromethyl) and tetrazole analogues of cinnamic acid with antibacterial activity. A bioisosteric approach
Autor/es:
MARTINEZ M. D.; MORA V.; BERTONCELLO L.; ZINI E.; GUIMARÃES T.; REGINATTO F. H.; BURTON G.; DURAN F. J.
Lugar:
Canela, Rio Grande do Sul, Brasil
Reunión:
Simposio; 6th Brazilian Symposium on Medicinal Chemistry; 2012
Institución organizadora:
Brazilian Chemical Society (SBQ). Division of Medicinal Chemistry.
Resumen:
The cinnamic and caffeic (3,4-dihydroxycinnamic
acid) acid scaffolds are extremely versatile
pharmacophores and are found in a number of
biologically active synthetic and natural molecules.
Their derivatives showed antibacterial, antiviral, antisclerotic,
anti-HIV and anti-tumor activities among
others. In particular, caffeic acid amides and related
compounds have significant antibacterial activity
against M. tuberculosis and S. aureus strains.1a-f
Recently, we prepared a series of amides of
3-(difluoromethyl)cinnamic acid and tested them
against a panel of 14 microorganisms (Gram + and
Gram -). N-isopropyl-3-(difluoromethyl)-4-methoxycinnamyl
amide (1) showed good activity (MIC 8
μg/ml M. smegmatis).2a-b
Our approach was to optimize the activity of 1 and
evaluate the effect of the bioisosteric replacement of
the carboxyl group by a tetrazole ring.
