New Hydrazide-hydrazone Derivatives of Quinoline 3-Carboxylic Acid Hydrazide: Synthesis, Theoretical Modeling and Antibacterial Evaluation

Abstract

A series of biologically active 3-quinoline carboxylic acid hydrazide-hydrazones has been synthesized from 3-quinoline carboxylic acid hydrazide and a variety of aldehydes, with moderate to good yields. The chemical structures of the new products were confirmed by elemental analysis, IR, and 1H NMR, 13C NMR spectral data. The structural and frontier molecular orbital (FMO) properties and the density functional theory (DFT) calculations were conducted for the new compounds. The new hydrazide-hydrazones exhibited low to moderate antibacterial activity against Staphylococcus aureus and Esherichia coli in comparison with gentamycin. Among the tested compounds, compounds 9 and 13 were found to be the most active. Phthalimide derivative 2 of 3-quioline carboxylic acid hydrazide showed remarkable antibacterial activity.

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

“…Amongst the derivatives, 20 indicated the maximum activity (ZOI=17 mm) and comparable to standard drug gentamicin (ZOI=19.1 mm against S. aureus and 21.2 mm against E. coli ). SAR study indicated that substitution by 1,3‐dioxoisoindolin‐2‐yl moiety ( 20 ) in hydrazine enhanced the antibacterial activity of quinoline‐based compounds [80] …”

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

“…The latter intermediate dicarbonyl compound (2) was produced by Calkylation of the commercially available 2,4'-dibromoacetophenone (1) and ethyl 3-oxobutanoate. A hydrazinolysis with excess hydrazine-hydrate was also carried out to obtain the desired Npyrrolylhydrazide (5). For the production of the pyrrole-based hydrazide-hydrazones (5a-d), we utilized equimolar concentrations of the hydrazide 5 (Scheme 1) and the corresponding carbonyl partners (a-d) (Figure 1).…”

“…The pharmacological profile of the latter functional group is broad, and it includes antimicrobial, antiseptic, antidepressant, antitubercular, antifungal, anti-inflammatory, antiviral, and antiprotozoal effects. 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.…”

“…8 Furthermore, higher yields, rapid cooling potential, higher product purities, minor pollution of the environment, and easier work-up practices have been discussed. 9,10 Therefore, the aim was to implement both conventional and microwave-assisted synthesis of one N-pyrrolylcarboxylic acid (3), the corresponding hydrazide (5), and four novel hydrazide-hydrazones (5a-d). The antioxidant properties of the latter were assessed with DPPH (2,2-diphenyl-1-picrylhydrazyl) and ABTS (2,2'-azino-bis(3ethylbenzothiazoline-6-sulfonic acid)) scavenging tests.…”

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

“…Hydrazide-hydrazone derivatives are present in many bioactive molecules and display a wide variety of biological activities, such as antibacterial, antitubercular, antifungal, anticancer, anti-inflammatory, anticonvulsant, antiviral, and antiprotozoal action [12][13][14][15]. Therefore, many medicinal chemists are interested in the synthesis of various hydrazidehydrazones and the evaluation of their biological activities.…”