Enantioselective MW-US-assisted Synthesis, DFT Simulation and Molecular Docking of Spiro Pyrrolidine-2,3'-Thieno [2,3-d]Pyridazin-Hydrazide as Green Agricultural Product

• Published in: Polycyclic aromatic compounds Vol. 44; no. 5; pp. 2991 - 3008
• Main Authors: Rizk, Sameh A., Alzahrani, Abdullah Y., Abdo, Abdullah M.
• Format: Journal Article
• Language: English
• Published: Philadelphia Taylor & Francis 27.05.2024; Taylor & Francis Ltd
• Subjects: Acrylic acid; agriculture product; Antiinfectives and antibacterials; antimicrobial activities; Bacteria; Bacterial diseases; Binding; Biomolecules; Chemical synthesis; Density functional theory; DFT; Enantiomers; Ethanol; green chemistry; Heterocyclic compounds; Insects; Irradiation; Larvae; Microbicides; Microorganisms; Microwave radiation; Molecular docking; Planar structures; Pyrrolidine; Spiropyridazine; Sustainable agriculture; Thioglycolic acid; United States > US
• ISSN: 1040-6638; 1563-5333
• DOI: 10.1080/10406638.2023.2227316

Effecient green tools of β-(3,4-dichlorophenyl-acrylic acid, thioglycolic acid and β-(2-oxopyrrolidin-1-yl) ethanol under ultrasonic and microwave-assisted irradiation (MW-US) as found to be a simple approach for preparing interesting Spiro derivatives. A novel class Spiro-pyrrolidine-2,3'-thieno[2,3-d]pyridazine derivatives (2-6) were efficiently synthesized via one-pot multicomponent reactions. Ethoxy acetyl Spiro pyrrolidine-2,3'-thieno[2,3-d]pyridazin-hydrazide (5) assessed as ecofriendly microbicidal and insecticidal activities to establish a structure-activity relationship. Elemental analysis and spectroscopic data were used to describe the structures of all synthesized products. The Spiro-heterocyclic compounds are exclusive non-planar structures and branded for binding to biomolecules. The microbicidal and insecticidal activities of the compounds were investigated on ATCC coded test microorganisms upon the applied dose and time was studied through two kinetic study. The interaction with these antibacterial and insect's third instar larvae was medicinal and economically valuable. The preliminary testing demonstrated flourishing microbicidal capability to prevent the growth of threatening pathogenic bacteria as well as blossoming insecticidal efficacy. Moreover, Molecular docking and density functional theory simulations can be used to validate the experimental results. Also, we utilized the docking approach with secondary bacterial infection indicated that Ethoxy acetyl Spiro hydrazide (5) and Spiro arylidene hybrid (6) have exerted the strongest docking binding value against the active sites of 6LU7.