Substituted naphthalen-1-yl-acetic acid hydrazides: synthesis, antimicrobial evaluation and QSAR analysis

A series of naphthalen-1-yl-acetic acid benzylidene/(1-phenyl-ethylidene)-hydrazides (1-36) was synthesized and tested, in vitro, for antiviral, antibacterial and antifungal activities. The antibacterial and antifungal screening results indicated that compounds having o-bromo, methoxy and hydroxy substitutents were the most active ones. The results of antiviral evaluation showed that none of the synthesized derivatives inhibited the viral infection at subtoxic concentrations. QSAR investigations revealed that the multi-target QSAR model was more effective in describing the antimicrobial activity than the one-target QSAR models. Further, it revealed the importance of the partition coefficient (log P) followed by energies of the highest occupied molecular orbital (HOMO) and topological parameters, molecular connectivity indices (1χ, 3χ and 3χv) in describing the antimicrobial activity of substituted hydrazides.