Substituted benzoic acid benzylidene/furan-2-yl-methylene hydrazides: synthesis, antimicrobial evaluation and QSAR analysis

Abstract

Development of new antimicrobial agents is increasingly important due to the resistance of microbes to the known antimicrobial drugs. In the present work substituted benzoic acid hydrazides (1-10) were condensed with substituted aromatic and heteroaromatic aldehydes to yield the target products (11)(12)(13)(14)(15)(16)(17)(18)(19)(20). The synthesized compounds were tested in vitro for their antimicrobial activity against Gram positive, Gram negative bacterial and fungal species. The QSAR analysis applied to determine the correlation of antimicrobial activity of substituted hydrazide derivatives with their physicochemical properties indicated the importance of electronic parameters, dipole moment (µ) and energy of lowest unoccupied molecular orbital (LUMO) in describing antibacterial and antifungal activity respectively.

Infrared and ¹³C NMR Spectral Studies of some Aryl Hydrazides: Assessment of Substituent Effects

“…All substituted benzohydrazides have been synthesized and analyzed their purities by literature method [4]. The general structure of the synthesized benzohydrazide is shown in Fig.…”

“…Hydrazides are one of the derivatives of acid chloride compounds. They possess important biological activities due to their moiety contains carbonyl, N-N groups and polar substituents in aryl ring [1][2][3][4][5][6][7][8]. Spectroscopic data were utilized for the study of QSAR, QPR, QSR of organic compounds [9,10].…”

Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings

“…This class of compounds and their derivatives such as hydrazones have been described as useful synthons of various heterocyclic rings of different ring sizes with one or several heteroatoms that exhibit interesting applications as pharmaceuticals, , herbicides, antibacterial agents, and dyes. , The synthetic strategy, in general, for various heterocyclic moieties from hydrazide precursors, has been made by cyclization or cycloaddition with numerous reagents . Hydrazide analogues also possess other biological activities like anticonvulsant, antidepressant, anti-inflammatory, antimalarial, antimycobacterial, anticancer, and antimicrobial − activities.…”

Efficient Oxidative Cyclisation of Acid Hydrazides to 2,5-Disubstituted 1,3,4-Oxadiazoles Catalysed by Bu4NI with t-BuOOH as Oxidant

“…Typical procedure Preparation of acid hydrazides: 41 A mixture of carboxylic acid ester (10 mmol) and hydrazine hydrate (40.0 mmol, 80% in H 2 O) in ethanol (20 mL) was refluxed overnight. After cooling to room temperature, the solution was concentrated in vacuo and the crude product was washed with hexane (2 × 10 mL) to give the corresponding acid hydrazide.…”