Abstract
In this study, we used oxazinethione as a perfect precursor to synthesize new pyrimidine and pyrazole derivatives with potent biological activities. Biological activities were determined for all compounds against A. flavus, E. coli, S. aureus, and F. moniliform. Compounds 3, 4a-b, and 5 exhibited higher activities toward A. flavus, E. coli, S. aureus, and F. moniliform; this was indicated through the MIC (minimum inhibitory concentration). At the same time, anticancer activities were determined through four cell lines, Ovcar-3, Hela, MCF-7, and LCC-MMk. The results obtained indicated that compound 5 was the most potent compound for both cell lines. Molecular docking was studied by the MOE (molecular operating environment). The in silico ADME of compounds 2 and 5 showed good pharmacokinetic properties. The present research strengthens the applicability of these compounds as encouraging anticancer and antibacterial drugs. Moreover, JAGUAR module MD simulations were carried out at about 100 ns. In addition, spectroscopic studies were carried out to establish the reactions of the synthesized structure derivatives.
Highlights
Oxazinethione is a bright nucleus in many pharmacological studies and applications
An easy way of synthesizing and studying the biological activities of oxazine pyrimidine and oxazine pyrazole derivatives was reported with promising results [6]
The results showed good pharmacokinetic properties in which compounds 2b and 5 have high gastrointestinal absorption
Summary
Oxazinethione is a bright nucleus in many pharmacological studies and applications. One of oxazinethione is compound 1a-b which was prepared in our laboratory Figure 1. Oxazinethione derivative (1a) reacted with urea and thiourea in n-butanol by boiling, which gave 2-(tetrabromophthalimidomethyl-6-phenyl-5-cyano-1,3-oxazino[4,5-e]-1,3-. The structures of both (2a and 2b) were proved by analytical data, and the IR spectra of (2a) and (2b) exhibited absorptions at 1720–1710 cm−1 (CO), 2230–2220 cm−1 (CN), 1200–1190 cm−1 (CS), and 3380–. Compound (1a) reacted with hydrazine hydrate in boiling n-butanol, resulting in 2-(tetrabromophalimidmethyl)-6-phenyl-5-yano-1,3-oxazino[4,5-d]-1,2-pyrazole2[H]-3-one (3), Scheme 2. Oxazinethione derivative (1a) reacted with urea and thiourea in n-butanol by boiliSncgh,ewmhei1c.hSygnatvhees2i-s(oteftcroambrpoomunodpsh2tha-abli.midomethyl-6-phenyl-5-cyano-1,3-oxazino[4,5-e]-1,3pyrimidine-3-[H]-2,4-dione (2a) and 2-(tetrabromophthalimidomethyl-6-phenyl-5-cyano-1,3oxazino[4,5-e]-1,3-pyrimidine-3-[H]-2-thione-4-one (2b). The structures of both (2a and 2b) were proved by analytical data, and the IR spectra of (2a) and (2b) exhibited absorptions at 1720–1710 cm−1 (CO), 2230–2220 cm−1 (CN), 1200–1190 cm−1 (CS), and 3380–3370 cm−1 (NH). FOivglFiciungaerurser.-e33,3..aInnIndhihbLiitbLioiCnti-oaMnndKaI2Cn5cd0 eolfIlCslei5lne0cetoesd.f csoemlepcotuenddscionmDMpoSOunsodlustiionnsDtoMwaSrOd MsCoFlu-7t,iHonelsa, tOovwcaarr-3d, aMndCLFLC-7-M, HK2ecleal,l
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