Brominated 1,4-dihydropyridine derivatives as potential insecticides against the cotton aphid (Aphis gossypii): synthesis, characterization, biological evaluation, and molecular docking studies.
6 affiliations
- 1Department of Biological Sciences, College of Science, University of Jeddah Jeddah Saudi Arabia [email protected].
- 2Department of Chemistry, Faculty of Science, Umm Al-Qura University 21955 Makkah Saudi Arabia [email protected] [email protected].
- 3Department of Chemistry, Faculty of Science, Sohag University Sohag 82524 Egypt [email protected].
- 4Department of Chemistry, Faculty of Science, King Khalid University Abha 61413 Saudi Arabia.
- 5Plant Protection Research Institute, Agricultural Research Center 12112 Giza Egypt.
- 6Department of Chemistry, Jamoum University College, Umm Al-Qura University 21955 Makkah Saudi Arabia.
Abstract
A new series of brominated 1,4-dihydropyridine derivatives bearing various aryl and heteroaryl substituents was successfully synthesized through a microwave-assisted multicomponent Hantzsch reaction followed by bromination under solar irradiation. The synthesized compounds were characterized by IR, 1H NMR, 13C NMR spectroscopy and elemental analyses. Their insecticidal activities were evaluated against adult and nymphal stages of the cotton aphid, Aphis gossypii, using the leaf-dipping bioassay technique. Biological evaluation demonstrated that all synthesized derivatives exhibited significant insecticidal activity, with nymphs showing greater susceptibility than adults. Among the tested compounds, derivative 5e displayed the highest activity, with LC50 values of 0.18 and 3.03 mg L-1 against nymphs and adults, respectively. To investigate the potential mode of action, molecular docking studies were performed against acetylcholinesterase (AChE). All compounds showed favorable binding affinities toward the enzyme, ranging from -8.3 to -9.0 kcal mol-1. Compound 5d exhibited the strongest predicted binding affinity (-9.0 kcal mol-1), while the biologically most active derivative, 5e, showed a docking score of -8.7 kcal mol-1. The combined biological and computational results indicate that brominated 1,4-dihydropyridine derivatives represent promising lead structures for the development of new insecticidal agents against A. gossypii.
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BibTeX
@article{hakeem2026brominated,
title = {{Brominated 1,4-dihydropyridine derivatives as potential insecticides against the cotton aphid (Aphis gossypii): synthesis, characterization, biological evaluation, and molecular docking studies.}},
author = {Israa J Hakeem and Munirah M Al-Rooqi and Moumen S Kamel and Abdullah Yahya Abdullah Alzahrani and Ahmed G Khamis and Ali M Drar and Amer A Amer and Rabab S Jassas and Saleh A Ahmed and Mohamed Sharaf},
journal = {RSC advances},
year = {2026},
month = oct,
doi = {10.1039/d6ra08804j},
url = {https://europepmc.org/article/MED/42953411},
note = {CC BY},
}
RIS
TY - JOUR
TI - Brominated 1,4-dihydropyridine derivatives as potential insecticides against the cotton aphid (Aphis gossypii): synthesis, characterization, biological evaluation, and molecular docking studies.
AU - Israa J Hakeem
AU - Munirah M Al-Rooqi
AU - Moumen S Kamel
AU - Abdullah Yahya Abdullah Alzahrani
AU - Ahmed G Khamis
AU - Ali M Drar
AU - Amer A Amer
AU - Rabab S Jassas
AU - Saleh A Ahmed
AU - Mohamed Sharaf
PY - 2026
DA - 2026/10/28
JO - RSC advances
DO - 10.1039/d6ra08804j
UR - https://europepmc.org/article/MED/42953411
AB - A new series of brominated 1,4-dihydropyridine derivatives bearing various aryl and heteroaryl substituents was successfully synthesized through a microwave-assisted multicomponent Hantzsch reaction followed by bromination under solar irradiation. The synthesized compounds were characterized by IR, 1H NMR, 13C NMR spectroscopy and elemental analyses. Their insecticidal activities were evaluated against adult and nymphal stages of the cotton aphid, Aphis gossypii, using the leaf-dipping bioassay technique. Biological evaluation demonstrated that all synthesized derivatives exhibited significant insecticidal activity, with nymphs showing greater susceptibility than adults. Among the tested compounds, derivative 5e displayed the highest activity, with LC50 values of 0.18 and 3.03 mg L-1 against nymphs and adults, respectively. To investigate the potential mode of action, molecular docking studies were performed against acetylcholinesterase (AChE). All compounds showed favorable binding affinities toward the enzyme, ranging from -8.3 to -9.0 kcal mol-1. Compound 5d exhibited the strongest predicted binding affinity (-9.0 kcal mol-1), while the biologically most active derivative, 5e, showed a docking score of -8.7 kcal mol-1. The combined biological and computational results indicate that brominated 1,4-dihydropyridine derivatives represent promising lead structures for the development of new insecticidal agents against A. gossypii.
SN - 2046-2069
ER -