Synthesis, Characterization and Biological Activities of Some New Acid Hydrazones Derived from Ethyl-2-[(N-acetyl)-2,5-dichloroanilido] Acetohydrazide

Abstract

A series of new acid hydrazones have been synthesized by the reaction of ethyl-2-[(N-acetyl)- 2,5-dichloroanilido] acetohydrazide with various carbonyl compounds in 30-92 % yield. Hydrazones are white, brown and yellow colour solids, having high melting points. Newly synthesized compounds (1-9, 12-17) have been tested for their antibacterial activity against gram positive bacteria S. albus, S. aureus and gram negative bacteria E. coli and Pseudomonas piosineus. The compound 2, 3, 5, 12, 13, 14 and 15 shown significant activity and compound 1, 4, 6, 7, 8, 9, 16 and 17 have shown moderate activity. The same compounds were tested for their antifungal activity against Candida albicans, Aspergillus niger and Alternaria alternata at concentration of 30 mg/mL using savored dextrose agar media. The compounds 2, 5, 12, 13, 14 and 15 shown significant activities and compounds 1, 4, 8, 9, 16 and 17 have shown moderate activity against Candida albicans and Aspergillus niger. All the other compounds did not show significant activity against the fungi at the concentration used. Some new compounds have been tested for anti tubercular activity in vitro using Mycobacterium tuberculosis. The compounds were incorporated into Lowenstein Jensen egg medium having concentrations of 10 and 100 mg/mL and were inoculated with Mycobacterium tuberculosis, H27, Rv strains, incubated at 37 ºC and observed, ethyl-2-[(N-acetyl)-2,5-dichloroanilido] acetohydrazide, ethyl-2-[(N-acetyl)-2,5- dichloroanilido] acetohydrazone of 4-N,N-bis-2'-cyanoethylamino benzaldehyde, ethyl-2-[(Nacetyl)- 2,5-dichloroanilido]acetohydrazone of 2-methyl-4-N,N-bis-2'-cyanoethylaminobenzaldehyde and ethyl-2-[(N-acetyl)-2,5-dichloroanilido] acetohydrazone of 5-chloro salicylaldehyde inhibited the growth of Mycobacterium tuberculosis at 100 mg/mL concentration other compounds were found to be inactive.