Synthesis and Biological Activity Evaluation of 3,4,7,8-Tetrahydro-3,3-Dimethyl-11-Aryl-2H-Pyridazino[1,2-a]Indazole-1,6,9(11H)-Triones by Using an Acidic Ionic Liquid 1-Methylimidazolium Trinitromethanide {[HMIM]C(NO2)3} as a Green Catalyst

3,4,7,8-tetrahydro-3,3-dimethyl-11-aryl-2H-pyridazino[1,2-a]indazole-1,6,9(11H)-triones 5a-j were synthesized by a one-pot cyclocondensation of four components such as succinic anhydride, hydrazine hydrate, benzaldehyde derivatives and dimedone at room temperature through a multi-component reaction and solvent-free condition by using 1-methyl imidazolium trinitromethanide {[HMIM]C(NO2)(3)} as a very effective ionic liquid catalyst. All synthesized compounds which are soluble in DMSO were subjected to antibacterial activity assay against Escherichia coli, Salmonella enteritidis, Staphylococcus aureus, and Bacillus cereus. Results showed that the compounds had antibacterial activity against some bacteria tested. In addition, the antioxidant activity of the compounds was evaluated by DPPH free radical scavenging assay. Our results indicated that most of the compounds had excellent dose-dependent antiradical properties. Based on obtained data, the compounds possessed moderate to excellent bactericidal effect on both Gram-positive and Gram-negative bacteria. Moreover, the compounds 5b and 5g exhibited the most anti-proliferative potencies against MCF-7 (breast carcinoma), A549 (non-small lung carcinoma) and AGS (gastric carcinoma) cell lines.

Automated summary

3,4,7,8-tetrahydro-3,3-dimethyl-11-aryl-2H-pyridazino[1,2-a]indazole-1,6,9(11H)-triones were synthesized using a one-pot cyclocondensation method with succinic anhydride, hydrazine hydrate, benzaldehyde derivatives and dimedone. The compounds exhibited antibacterial activity against both Gram-positive and Gram-negative bacteria, as well as anti-proliferative effects on breast, lung, and gastric carcinoma cell lines.