Cargando…
Green Design, Synthesis, and Molecular Docking Study of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora
[Image: see text] An efficient and environmentally friendly method was established for designing novel 3-amino-1,4-dihydroquinoxaline-2-carbonitrile (1) via the reaction of bromomalononitrile and benzene-1,2-diamine under microwave irradiation in an excellent yield (93%). This targeted amino derivat...
Autores principales: | , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
|
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9366785/ https://www.ncbi.nlm.nih.gov/pubmed/35967065 http://dx.doi.org/10.1021/acsomega.2c03332 |
_version_ | 1784765644033490944 |
---|---|
author | Alanazi, Mariam Azzam Arafa, Wael A.A. Althobaiti, Ibrahim O. Altaleb, Hamud A. Bakr, Rania B. Elkanzi, Nadia A. A. |
author_facet | Alanazi, Mariam Azzam Arafa, Wael A.A. Althobaiti, Ibrahim O. Altaleb, Hamud A. Bakr, Rania B. Elkanzi, Nadia A. A. |
author_sort | Alanazi, Mariam Azzam |
collection | PubMed |
description | [Image: see text] An efficient and environmentally friendly method was established for designing novel 3-amino-1,4-dihydroquinoxaline-2-carbonitrile (1) via the reaction of bromomalononitrile and benzene-1,2-diamine under microwave irradiation in an excellent yield (93%). This targeted amino derivative was utilized for the construction of a series of Schiff bases (8–13). A new series of thiazolidinone derivatives (15–20) were synthesized in high yields (89–96%) via treatment of thioglycolic acid with Schiff bases (8–13) under microwave irradiation in high yields (89–96%). Moreover, new pyrimidine derivatives (26–30 and 35–38) were prepared by treatment of compound 1 with arylidenes (21–25) and/or alkylidenemalononitriles (31–34) using piperidine as a basic catalyst under microwave conditions. Based on elemental analyses and spectral data, the structures of the new assembled compounds were determined. The newly synthesized quinoxaline derivatives were screened and studied as an insecticidal agent against Aphis craccivora. The obtained results indicate that compound 16 is the most toxicological agent against nymphs of cowpea aphids (Aphis craccivora) compared to the other synthesized pyrimidine and thiazolidinone derivatives. The molecular docking study of the new quinoxaline derivatives registered that compound 16 had the highest binding score (−10.54 kcal/mol) and the thiazolidinone moiety formed hydrogen bonds with Trp143. |
format | Online Article Text |
id | pubmed-9366785 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-93667852022-08-12 Green Design, Synthesis, and Molecular Docking Study of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora Alanazi, Mariam Azzam Arafa, Wael A.A. Althobaiti, Ibrahim O. Altaleb, Hamud A. Bakr, Rania B. Elkanzi, Nadia A. A. ACS Omega [Image: see text] An efficient and environmentally friendly method was established for designing novel 3-amino-1,4-dihydroquinoxaline-2-carbonitrile (1) via the reaction of bromomalononitrile and benzene-1,2-diamine under microwave irradiation in an excellent yield (93%). This targeted amino derivative was utilized for the construction of a series of Schiff bases (8–13). A new series of thiazolidinone derivatives (15–20) were synthesized in high yields (89–96%) via treatment of thioglycolic acid with Schiff bases (8–13) under microwave irradiation in high yields (89–96%). Moreover, new pyrimidine derivatives (26–30 and 35–38) were prepared by treatment of compound 1 with arylidenes (21–25) and/or alkylidenemalononitriles (31–34) using piperidine as a basic catalyst under microwave conditions. Based on elemental analyses and spectral data, the structures of the new assembled compounds were determined. The newly synthesized quinoxaline derivatives were screened and studied as an insecticidal agent against Aphis craccivora. The obtained results indicate that compound 16 is the most toxicological agent against nymphs of cowpea aphids (Aphis craccivora) compared to the other synthesized pyrimidine and thiazolidinone derivatives. The molecular docking study of the new quinoxaline derivatives registered that compound 16 had the highest binding score (−10.54 kcal/mol) and the thiazolidinone moiety formed hydrogen bonds with Trp143. American Chemical Society 2022-07-27 /pmc/articles/PMC9366785/ /pubmed/35967065 http://dx.doi.org/10.1021/acsomega.2c03332 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Alanazi, Mariam Azzam Arafa, Wael A.A. Althobaiti, Ibrahim O. Altaleb, Hamud A. Bakr, Rania B. Elkanzi, Nadia A. A. Green Design, Synthesis, and Molecular Docking Study of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora |
title | Green Design, Synthesis,
and Molecular Docking Study
of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora |
title_full | Green Design, Synthesis,
and Molecular Docking Study
of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora |
title_fullStr | Green Design, Synthesis,
and Molecular Docking Study
of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora |
title_full_unstemmed | Green Design, Synthesis,
and Molecular Docking Study
of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora |
title_short | Green Design, Synthesis,
and Molecular Docking Study
of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora |
title_sort | green design, synthesis,
and molecular docking study
of novel quinoxaline derivatives with insecticidal potential against aphis craccivora |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9366785/ https://www.ncbi.nlm.nih.gov/pubmed/35967065 http://dx.doi.org/10.1021/acsomega.2c03332 |
work_keys_str_mv | AT alanazimariamazzam greendesignsynthesisandmoleculardockingstudyofnovelquinoxalinederivativeswithinsecticidalpotentialagainstaphiscraccivora AT arafawaelaa greendesignsynthesisandmoleculardockingstudyofnovelquinoxalinederivativeswithinsecticidalpotentialagainstaphiscraccivora AT althobaitiibrahimo greendesignsynthesisandmoleculardockingstudyofnovelquinoxalinederivativeswithinsecticidalpotentialagainstaphiscraccivora AT altalebhamuda greendesignsynthesisandmoleculardockingstudyofnovelquinoxalinederivativeswithinsecticidalpotentialagainstaphiscraccivora AT bakrraniab greendesignsynthesisandmoleculardockingstudyofnovelquinoxalinederivativeswithinsecticidalpotentialagainstaphiscraccivora AT elkanzinadiaaa greendesignsynthesisandmoleculardockingstudyofnovelquinoxalinederivativeswithinsecticidalpotentialagainstaphiscraccivora |