Efficient access to some new pyrimidine derivatives and their antimicrobial evaluation

Abstract

1-[4-(3-Hydroxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]eth anone (1) was used as a precursor for heterocyclic synthesis. Condensation of compound 1 with monochloroacetic acid and benzaldehyde gave thiazolopyrimidine 2 which in turn underwent cyclization with malononitrile dimmer to afford malononitrile derivative 3. Also, the reaction of compound 1 with benzaldehyde under a basic condition produced chalcone 4. Chalcone 4 can be used as a key intermediate for further preparation of heterocyclic compounds. In addition, compound 1 was allowed to react with malononitrile dimmer and/or ethyl chloroacetate to give pyrimidines 8 and 9, respectively.Alkylation of compound 8 with ethyl chloroacetate afforded S-alkylated product 10 which was treated with hydrazine hydrate to yield the hydrazino derivative 11. Alternative synthesis of compound 10 was taken place through reaction of compound 9 with malononitrile dimmer. The biological activity of the synthesized compounds was investigated. Compounds 1, 4, 5, and 8 recorded high activities against Gram positive bacteria (S. aureus). Structures of the new synthesized compounds were elucidated by elemental analysis and spectral data.

Design, Synthesis, and Antifungal Activity of Novel 1,2,4-Triazolo[4,3-c]trifluoromethylpyrimidine Derivatives Bearing the Thioether Moiety

“…Pyrimidine is an essential part of DNA and RNA in living system ( Kumar and Narasimhan, 2018 ). Pyrimidine derivatives exhibited diverse biological properties, such as antineoplastic ( Kesari et al, 2021 ), anti-inflammatory ( Abdel-Aziz et al, 2021 ), antiviral ( Abu-Zaied et al, 2021 ), and antimicrobial ( El-mahdy and Farouk, 2021 ) activities. In addition, fused pyrimidine systems, such as pyrrolo [3,2- d ]pyrimidine and 1,2,4-triazolo[1,5- a ]pyrimidine, also possess extensive biological activities ( Cawrse et al, 2018 ; Wang et al, 2019 ; Baillache and Unciti-Broceta, 2020 ; Basyouni et al, 2021 ; Wang R.-X.…”