Chemoselective synthesis of tunable poly-functionalized binary pyrazolyl and annulated pyrazolo/pyrido anchored on quinolinone: insecticidal and antioxidant studies

Abstract

The present work is directed to synthesize new tolerance binary pyrazolylquinolinone such as pyrazolylquinolinone, 1-phenylpyrazolyl)quinolinone and 1,2,4-triazolyl)pyrazolyl)quinolinone and fused pyrazolo-/pyridoquinolinone hybrids as pyrazolo[4,3-c]quinolinone, benzo[h][1,6]naphthyridinedione, tetrahydrobenzo[h][1,6]naphthyridine-3-carbonitrile and 2,7-triazaindeno[4,5,6-de]anthracenol as prospective ingredients with the aim of assessment for their antioxidant and insecticidal potentiality. Additionally, in vitro and in vivo insecticidal bio-responses, cotton leafworm, Spodoptera littoralis (S. littoralis) and the cotton aphid were screened for the synthesized compounds. Interestingly, the most potent compounds were 11 and 5 with (LC₅₀ 119.79 and 164.63 mg L⁻¹) against S. littoralis. Furthermore, the influence of the tested compounds on biochemical parameters, including AChE, ATPase, total protein levels, detoxifying enzymes CaE, and GST were also inspected. Furthermore, the targeted compounds showed promising antioxidant activity comparable with ascorbic acid as the presence of both of functionalized quinolinone and pyrazole moieties increasing the scavenger radical inhibition. Finally, DFT calculations were implemented to investigate the electronic and structural properties of the synthesized scaffolds.