Design and Synthesis of 8-Trifluloromethyl-2-Thioquinazolin-(3H)-4-One Nucleosides

Abstract

Quinazolinone and thioquinazolinone are heterocyclic compounds that occupy a distinct place in the field of medicinal chemistry. Quinazoline-2,4-diones and thioquinazolinones bearing a trifluoromethyl group derivatives were inhibitors of human immunodeficiency virus-1 reverse transcriptase, antagonists at ionotropic glutamate receptors and anticancer compound trifluoromethyl-substituted pyrazole N-nucleoside. 2-Amino-3-trifluloromethyl benzoic acid 1 isothiocyanate KNCS and triethylamine in absolute ethanol was heated under reflux for 3 h. Synthesis of 8-trifluloromethyl-2-thioquinazolin-(1H,3H)-4-one 2. which have been ribosylated by coupling with 1-O-acetyl-2,3,5-tri-O-benzoyl-\(\beta\) -D-ribofuranose 4 by using the silylation method, afforded \(\beta\)-anomeric of the benzoylated nucleoside derivatives 5. Debenzoylation of 5 by sodium metal in dry methanol to afford the corresponding free nucleosides 6. The structures of the newly synthesised compounds have been confirmed on the basis of elemental analyses, IR, ¹HNMR, ¹³CNMR and Mass spectral data.The structures of the products 2-6 were established and confirmed.