Synthesis of Novel Gabapentin Scaffold Derived Hydrazide-hydrazones for Potential Antimicrobial agents and Antioxidants

Abstract

Twelve new analogues of gabapentin (GBP) derived hydrazide-hydrazone scaffolds were produced by using various electronically and structurally divergent aromatic aldehydes. All the hydrazones were obtained in moderate to good yields (66-82%) by heating the GBP hydrazide with respective aldehydes to a temperature of 45-65 °C for 4-7 h. Further, the compounds were explored for their antimicrobial activity on three different Gram positive (Micrococcus luteus, Streptococcus mutans, Enterococcus faecalis) and Gram negative bacterial strains (Salmonella enterica, Alcaligenes faecalis, Pseudomonas aeruginosa). The antibacterial results obtained were found to be good against Gram positive bacteria when compared to Gram negative bacteria. Moreover, the compounds were also screened for antioxidant activity at four different concentrations using the DPPH method and the results showed that some of the compounds were moderately active.

Quinoline Hydrazide/Hydrazone Derivatives: Recent Insights on Antibacterial Activity and Mechanism of Action

“…Metal complexes showed more antibacterial activity as compared to ligand molecules. Cu (65) depicted comparable antibacterial activity (ZOI = 32 mm) as standard drug amoxicillin (ZOI = 38 mm) against E. faecalis. SAR scrutiny demonstrated that the existence of alkoxy group at the 8 th position of the quinoline improved the activity.…”

“…Nitrofurazone, furazolidone, nitrofurantoin, isoniazid etc ., are pharmacologically active antibacterial drugs that contain hydrazide/hydrazone moiety (Figure 2). [63,64] Amongst various reported activities, the antibacterial activity of quinoline hydrazide/hydrazone derivatives is noteworthy [65–67] . The presence of polar and nonpolar moieties in quinoline hydrazide/hydrazone derivatives make them able to penetrate across the bacterial cell membrane (Figure 3).…”

“…[63,64] Amongst various reported activities, the antibacterial activity of quinoline hydrazide/hydrazone derivatives is noteworthy. [65][66][67] The presence of polar and nonpolar moieties in quinoline hydrazide/ hydrazone derivatives make them able to penetrate across the bacterial cell membrane (Figure 3). Moreover, clubbing of quinoline with hydrazide/hydrazone moiety provided the amphipathic properties, which enhanced the penetration of drug through the cell wall of the bacteria.…”

Design, microwave-assisted synthesis, biological evaluation, molecular docking and ADME studies of pyrrole-based hydrazide-hydrazones as potential antioxidant agents

“…5 Literature data describing the antioxidant properties of hydrazide-hydrazonebased compounds are also published. 6 Thus, an increasing number of medicinal chemists are interested in the design and synthesis of various compounds comprising a hydrazide-hydrazone moiety.…”