Green Design, Synthesis, and Molecular Docking Study of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora

Mariam Azzam Alanazi; Wael A A Arafa; Ibrahim O Althobaiti; Hamud A Altaleb; Rania B Bakr; Nadia A A Elkanzi

doi:10.1021/acsomega.2c03332

Green Design, Synthesis, and Molecular Docking Study of Novel Quinoxaline Derivatives with Insecticidal Potential against Aphis craccivora

ACS Omega. 2022 Jul 27;7(31):27674-27689. doi: 10.1021/acsomega.2c03332. eCollection 2022 Aug 9.

Authors

Mariam Azzam Alanazi¹, Wael A A Arafa^{1

2}, Ibrahim O Althobaiti³, Hamud A Altaleb⁴, Rania B Bakr⁵, Nadia A A Elkanzi^{1

6}

Affiliations

¹ Chemistry Department, College of Science, Jouf University, P.O. Box 2014, Sakaka 2014, Saudi Arabia.
² Chemistry Department, Faculty of Science, Fayoum University, P.O. Box 63514, Fayoum 63514, Egypt.
³ Department of Chemistry, College of Science and Arts, Jouf University, Sakaka 42421, Saudi Arabia.
⁴ Department of Chemistry, Faculty of Science, Islamic University of Madinah, Madinah 42351, Saudi Arabia.
⁵ Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt.
⁶ Chemistry Department, Faculty of Science, Aswan University, P.O. Box 81528, Aswan 81528, Egypt.

Abstract

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.