Synthesis, characterization and study of the fungicidal and carginogenic activity of new dialkylphosphorylacylhydrazones
Organophosphorus, hydrazones, acethylcolinesterase, post-harvest fungusand melanoma
The present work refers to the synthesis of novel dialkylphosphorylacylhydrazones that occurs in 3 reaction steps: the first step consisted in the synthesis of different dialkyl acetate phosphonoacetates obtained by the reaction of the ethylbromoacetate with the trialkyl phosphite of interest. The second step was the synthesis of acetic diethoxyphosphonylhydrazides which occured by reaction between dialkyl phosphonoacetates synthesized and hydrazine. The third and final ones occured by the condensation of acetic diethoxyphosphonylhydrazides with different heterocyclic aldehydes. The obtained compounds were characterized by 1-H and 13-C and 31-P NMR, infrared (IR) and mass spectroscopy (MS). In total, 17 unpublished compounds, namely one to 17, respectively, were obtained with diastereoisomeric mixture of preferential conformation E. The fungicidal activity of each synthesized molecule was tested against plant pathogens fungi responsible for postharvest diseases of economic importance such as Pilidium sp., Alternaria sp., Penicilium sp. and Colletotrichum gloeosporioides, however, they did not present fungicidal activity in the evaluated fungi. The compounds were further tested on melanoma cells, for the purpose of verify whether they have any activity in tumor growth of melanoma cells, but only compounds 2 and 10 showed some biological activity, although relatively low.After synthesis and purification of the synthesized compounds, they are checked against the acetylcholinesterase enzyme activity. The AChE enzyme inhibition assay has shown that compound 2 does not inhibit the enzyme along with compounds 3, 7, 8 and 16 while compound 13 in addition to compound 9 strongly inhibits AChE and even more inhibitors than the standard used, the Propoxur.