Design, synthesis and biological evaluation of N-(substituted benzylidene)-2/4-(1, 3 dioxoisoindolin-2-yl) alkanehydrazide
Annu Saini, Jyoti, Sweety Ranga, Aakash Deep and Rakesh Kumar Marwaha
There is an urgent need to discover/develop antimicrobial agents having higher efficacy and potency against the rapidly growing antibiotic resistant strains of pathogenic micro-organism. A series of new Isoindole-1, 3-dione derivatives were synthesized via reaction of phthalic anhydride with two amino acids under fused conditions. Esterification of N-phthaloyl alkanoic acid derivatives with methanol in the presence of sulfuric acid yielded the corresponding esters, whereas, the esterification with methanol in presence of thionyl chloride gave N-phthaloyl alkanoic acid acetyl chloride. Both the esters and acetyl chlorides so formed produce the corresponding N-phthaloyl acid hydrazides on reaction with hydrazine hydrate and ethanol. Further reaction with different benzaldehydes yielded the corresponding substituted benzylidene phthalimide derivatives. The structures of the synthesized compounds were confirmed from their analytical and spectral data such as IR spectra and 1H-NMR spectra.
The antimicrobial activity of synthesized compounds determined by tube dilution method against various microorganisms indicated compounds, 9, 18 and 22 as most active ones. The synthesized compounds were also screened for in vitro antidiabetic activity by inhibition of α-amylase enzyme and antioxidant activity by DPPH assay method. The compounds 6 and 11 exhibited excellent α-amylase inhibitory activity whereas the compounds 10 and 22 found to possess good antioxidant activity.
How to cite this article:
Annu Saini, Jyoti, Sweety Ranga, Aakash Deep, Rakesh Kumar Marwaha. Design, synthesis and biological evaluation of N-(substituted benzylidene)-2/4-(1, 3 dioxoisoindolin-2-yl) alkanehydrazide. Pharma Innovation 2018;7(7):205-214.