Synthesis, larvicidal efficiency and molecular docking studies of novel annulated pyrano[2,3-c]pyrazoles against Culex pipiens L. and Musca domestica L. larvae

[Display omitted] •Novel annulated pyrazolopyranopyrimidines were prepared.•The tested pyranopyrazole derivatives exhibited good larvicidal bioefficacy.•Iminoether 4 exhibited promising larvicidal efficiency.•Docking study of the inhibitory effects of synthesized molecules on nAChRs was evaluated. A...

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Published in:Bioorganic chemistry 2023-01, Vol.130, p.106258, Article 106258
Main Authors: El-Sayed, Mahmoud K.F., El-Shahawi, Manal M., Ali, Yasmeen M., Abdel-Haleem, Doaa R., Abu El-Azm, Fatma S.M.
Format: Article
Language:English
Subjects:
Enaminonitriles
Iminoethers
Insecticidal efficiency
Pyranopyrazoles
Pyrazolopyranopyrimidines
Pyrazolopyranotriazolopyrimidines
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Summary:[Display omitted] •Novel annulated pyrazolopyranopyrimidines were prepared.•The tested pyranopyrazole derivatives exhibited good larvicidal bioefficacy.•Iminoether 4 exhibited promising larvicidal efficiency.•Docking study of the inhibitory effects of synthesized molecules on nAChRs was evaluated. A number of novel annulated pyrazolopyranopyrimidines were prepared via reaction of iminoether of the corresponding 6-amino-5-cyano-pyrano[2,3-c]pyrazole derivative 1 with different nitrogen nucleophiles. The structure of the synthesized compounds was deduced based on IR, MS, 1H NMR and 13C NMR spectroscopic data. The larvicidal potency of the synthesized compounds against the lab and field strains of Culex pipiens and Musca domestica larvae was evaluated and the structure–activity relationship (SAR) was discussed. The assay revealed that the tested pyranopyrazole derivatives exhibited good larvicidal bio-efficacy whereas iminoether 4 exhibited the highest efficiency, for lab more than field strains of both species. Also, M. domestica larvae were more sensitive to tested compounds than C. pipiens. The field strain showed low resistance ratios to all compounds with only about 2 folds. The inhibitory effects of synthesized molecules on nAChRs were evaluated by molecular docking. Moreover, the cytotoxicity of the newly synthesized compounds against normal human fibroblasts (WI-38) was investigated. The cytotoxic assay showed that derivatives 4 and 5 were not harmful to normal fibroblasts.
ISSN:0045-2068
1090-2120
DOI:10.1016/j.bioorg.2022.106258