Efficient and Recoverable Bio-Organic Catalyst Cysteine for Synthesis, Docking Study, and Antifungal Activity of New Bio-Active 3,4-Dihydropyrimidin-2(1 H)-ones/thiones Under Microwave Irradiation

Nadia A A Elkanzi; Asmaa M Kadry; Rasha M Ryad; Rania B Bakr; Mahmoud Abd El Aleem Ali Ali El-Remaily; Ali M Ali

doi:10.1021/acsomega.2c02449

Efficient and Recoverable Bio-Organic Catalyst Cysteine for Synthesis, Docking Study, and Antifungal Activity of New Bio-Active 3,4-Dihydropyrimidin-2(1 H)-ones/thiones Under Microwave Irradiation

ACS Omega. 2022 Jun 23;7(26):22839-22849. doi: 10.1021/acsomega.2c02449. eCollection 2022 Jul 5.

Authors

Nadia A A Elkanzi^{1

2}, Asmaa M Kadry³, Rasha M Ryad⁴, Rania B Bakr⁵, Mahmoud Abd El Aleem Ali Ali El-Remaily³, Ali M Ali³

Affiliations

¹ Chemistry Department, College of Science, Jouf University, P.O. Box: 2014 Sakaka, Saudi Arabia.
² Chemistry Department, Faculty of Science, Aswan University, P.O. Box: 81528 Aswan, Egypt.
³ Chemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt.
⁴ Department of Botany and Microbiology, Faculty of Science, Sohag University, 82524 Sohag, Egypt.
⁵ Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Beni-Suef University, 62511 Beni-Suef, Egypt.

Abstract

An eco-friendly green bio-organic catalyst and low-cost 3,4-dihydropyrimidin-2(1H)-ones/thione derivatives 4-7 have been synthesized using a high-yield, synthetic method via a one-pot, three-component process between 4-formylphenyl-4-methylbenzenesulfonate (1), thiourea, or urea and ethyl acetoacetate or acetylacetone under microwave irradiation in aqueous media of water and ethanol (3:1 ratio) as a green solvent in the presence of cysteine as a new green bio-organic catalyst. The reaction between compound 1, 4-(carbamothioylhydrazono) methyl]phenyl 4-methyl benzenesulfonate (3c), and ethyl acetoacetate or acetylacetone under the same condition afforded novel pyrimidines. Similarly, compound 1 was allowed to react with a mixture of 4-(carbamothioylhydrazono)methyl]phenyl 4-methyl benzenesulfonate (3c) and ethyl acetoacetate or acetylacetone under the same condition to afford pyrimidine derivatives 8 and 9. Excellent yields (90-98%) were obtained within short reaction times, and problems associated with the toxic solvents used (cost, safety, and pollution) were avoided. The structures of the new compounds were elucidated by elemental and spectral analyses. All compounds were studied using molecular docking, and their antifungal activity was investigated.