ABSTRACT
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.
Subject(s)
Antitubercular Agents/isolation & purification , Antitubercular Agents/pharmacology , Mycobacterium tuberculosis/drug effects , Aldehydes/chemistry , Aldehydes/isolation & purification , Aldehydes/pharmacology , Antitubercular Agents/chemistry , Hydrazones/chemistry , Hydrazones/isolation & purification , Hydrazones/pharmacology , Microbial Sensitivity Tests , Molecular Structure , Quinolones/chemistry , Quinolones/isolation & purification , Quinolones/pharmacologyABSTRACT
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.