Isobutyrohydrazonoyl bromide 1 was used as a precursor for the synthesis of 4-imino-3-
isopropyl-1-(4-nitrophenyl)-1,4-dihydro-5H-pyrazolo[3,4-d]pyrimidin-5-amine 4, which was converted
into hydrazino derivative 5 by heating with hydrazine hydrate at reflux. Hydrazino, as well as imino
and amino derivatives, underwent condensation and cyclization reactions to give pyrazolo[3,4-
d]pyrimidine and pyrazolo[4,3-e][1,2,4]triazolo[3,4-c]pyrimidine derivatives, respectively. Antimicrobial
studies are performed using two-gram positive bacteria and two-gram negative bacteria. Data revealed
that compound 9a is the most promising antibacterial agent with high efficiency (low MIC value
(48 μg/ml)). The cytotoxic assay was investigated for in vitro antitumor screening against Caucasian
breast adenocarcinoma MCF7, hepatocellular carcinoma HepG2 and colon carcinoma HCT-116
cell lines. The results are compared with doxorubicin standard anticancer drugs as well as normal cell
lines like MCF10 and MCF12. Molecular docking was carried out for the highest potent compound 8c
with the binding site of dihydrofolate reductase enzyme DHFR PDB:ID (1DLS).
Keywords: Modeling simulation, DHFR, cytotoxicity, imino-amino, hydrazine hydrate, hydrazones, antibacterial activity.
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