RESUMO
Tuberculosis (TB) is a contagious disease caused by Mycobacterium tuberculosis, which remains a serious public health problem. The emergence of resistant bacterial strains has continuously increased and new treatment options are currently in need. In this work, we identified a new potential aldehyde-arylhydrazone-oxoquinoline derivative (4e) with interesting chemical structural features that may be important for designing new anti-TB agents. This 1-ethyl-N'-[(1E)-(5-nitro-2-furyl)methylene]-4-oxo-1,4-dihydroquinoline-3-carbohydrazide (4e) presented an in vitro active profile against M. tuberculosis H37Rv strain (minimum inhibitory concentration, MIC = 6.25 µg/mL) better than other acylhydrazones described in the literature (MIC = 12.5 µg/mL) and close to other antitubercular agents currently on the market. The theoretical analysis showed the importance of several structural features that together with the 5-nitro-2-furyl group generated this active compound (4e). This new compound and the analysis of its molecular properties may be useful for designing new and more efficient antibacterial drugs.
Assuntos
Antituberculosos/isolamento & purificação , Antituberculosos/farmacologia , Mycobacterium tuberculosis/efeitos dos fármacos , Aldeídos/química , Aldeídos/isolamento & purificação , Aldeídos/farmacologia , Antituberculosos/química , Hidrazonas/química , Hidrazonas/isolamento & purificação , Hidrazonas/farmacologia , Testes de Sensibilidade Microbiana , Estrutura Molecular , Quinolonas/química , Quinolonas/isolamento & purificação , Quinolonas/farmacologiaRESUMO
In the title compound, C(18)H(16)N(4)O(2), the plane defined by the ethyl C atoms and the attached N atom is inclined to the adjacent pyridine ring at an angle of 67.87â (16)°. The dihedral angle between the two heterocyclic rings is 3.33â (16)°. The mol-ecular conformation is stabilized by an intra-molecular N-Hâ¯O hydrogen bond and the crystal structure by inter-molecular C-Hâ¯O hydrogen bonds, forming a one-dimensional structure.