Synthesis, Structures, and Antibacterial Activities of Hydrazone Compounds Derived from 4-Dimethylaminobenzohydrazide

Guo-Xu He,Ling-Wei Xue

doi:10.17344/acsi.2020.6333

Abstract

A series of three new hydrazone compounds derived from the condensation reactions of 4-dimethylaminobenzohydrazide with 4-dimethylaminobenzaldehyde, 2-chloro-5-nitrobenzaldehyde and 3-methoxybenzaldehyde, respectively, were prepared. The compounds were characterized by elemental analysis, infrared and UV-vis spectra, HRMS, 1H NMR and 13C NMR spectra, and single crystal X-ray diffraction. Crystals of the compounds are stabilized by hydrogen bonds. The compounds were assayed for antibacterial (Bacillus subtilis, Escherichia coli, Pseudomonas fluorescence and Staphylococcus aureus) and antifungal (Aspergillus niger and Candida albicans) activities by MTT method. The results indicated that compound 2 is an effective antibacterial material.

Highlights

Hydrazone compounds have been reported to possess interesting biological activities
The emphasis on structural studies of hydrazone compounds is a consequence of our interests in compounds having potential biological activity
Hydrazone compounds have been used as preferred ligands in construction of versatile structures of complexes with various metal salts like manganese, copper, vanadium and zinc.[3]

Summary

Introduction

Hydrazone compounds have been reported to possess interesting biological activities. Some of the compounds are found to be useful for the treatment of inflammatory diseases and tumors,[1] and some of the compounds have antibacterial, antifungal, antiviral, and many other activities.[2] The emphasis on structural studies of hydrazone compounds is a consequence of our interests in compounds having potential biological activity. Hydrazone compounds have been used as preferred ligands in construction of versatile structures of complexes with various metal salts like manganese, copper, vanadium and zinc.[3] The complexes displayed interesting biological and catalytic activities. It was reported that the compounds bearing one or more halo-substituents on the aromatic ring have improved biological activities, especially for the antibacterial and antifungal activities.[4] the structure-activity relationship was not clear until now. As an extension of our work on the structures and antibacterial activities of such compounds, in the present paper, three new hydrazone compounds, N’-(4-dimethylaminobenzylidene)-4-dimethylaminobenzohydrazide (1), N’-(2chloro-5-nitrobenzylidene)-4-dimethylaminobenzohydrazide (2), and N’-(3-methoxybenzylidene)-4-dimethylaminobenzohydrazide (3) (Scheme 1), are reported

1. Materials and Methods

Results and Discussion

Conclusion