Anti-Hepatitis B Virus Activity of New N⁴-β-D-Glycoside Pyrazolo[3,4-d]pyrimidine Derivatives

Abstract

The reaction of 6-hydrazinyl-1,3-dimethylpyrimidine-2,4-(1H,3H)-dione (1) with ethoxymethylenemalononitrile afforded 5-amino-1-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-6-yl)-1H-pyrazole-4-carbonitrile (2). The latter was reacted with formamide and urea affording the corresponding 4-aminopyrazolo[3,4-d]pyrimidines 3 and 4. The reaction of monosaccharide aldoses with 3 and 4 gave stereoselectively the β-N-glycosides 5a -d and 6a -d which were treated with acetic anhydride in pyridine to afford the corresponding acetylated derivatives 7a -d and 8a -d. The prepared compounds were tested for their antiviral activity against hepatitis B virus (HBV) and showed moderate to high activities.

Click chemistry based synthesis, cytotoxic activity and molecular docking of novel triazole-thienopyrimidine hybrid glycosides targeting EGFR

“…As a consequence of the above findings, it is assumed that novel hybrid structures possessing the three pharmacophoric systems could be of biological interest. We have continuing research interest for discovering potent and selective anticancer compounds 38,39 by the synthesis of new heterocyclic glycosides with modified base and/or glycon constituent. Owing to the significance of the above findings, in the current study, a number of molecular hybrids of thienopyrimidine linked triazole glycosides were synthesised and studied for their anticancer activity in addition to docking studies and EGFR kinase inhibition investigation.…”

Synthesis and Antimicrobial Activity of New Substituted 5‐(Pyridine‐3‐yl)‐1,3,4‐Thiadiazoles and Their Sugar Derivatives

“…Furthermore, the glycosylthio heterocycles [14,15] and the acyclic nucleoside [16][17][18] analogs including modifications of both the glycon and aglycon parts have stimulated extensive research as biological inhibitors [19,20]. In view of the above facts and our interest [19,[22][23][24][25] in the attachment of carbohydrate residues to heterocycles to find new biologically active leads, we report here the synthesis and antimicrobial activity of new Substituted 5-(pyridine-3-yl)-1,3,4-thiadiazoles, their sugar hydrazones and acyclic C-nucleoside analogs as well as the corresponding glycoside derivatives. In view of the above facts and our interest [19,[22][23][24][25] in the attachment of carbohydrate residues to heterocycles to find new biologically active leads, we report here the synthesis and antimicrobial activity of new Substituted 5-(pyridine-3-yl)-1,3,4-thiadiazoles, their sugar hydrazones and acyclic C-nucleoside analogs as well as the corresponding glycoside derivatives.…”

Synthesis and Antimicrobial Activity of New Thiazole Derivatives and Their Glucoside and Acyclic Nucleoside Analogs

“…Novel lead compounds containing thiazolyl moiety attached to pyrazolyl ring systems have been shown to possess pronounced dual anti‐inflammatory and antimicrobial activities. Furthermore, nucleoside analogs are structurally, metabolically, and pharmacodynamically related agents that have diverse biological actions and therapeutic effects including antiviral and antitumor activities. The above facts and our interest in the attachment of carbohydrate moieties to newly synthesized heterocycles searching for new biologically active leads promoted us to synthesize new substituted thiazoles glucosides and their acyclic analogous and evaluate their antimicrobial activity.…”