Nucleic Acid Components and Their Analogues: A Novel and Efficient Method for the Synthesis of a New Class of Bipyridyl and Biheterocyclic-Nitro Gen Thioglycosides From Pyridine-2(1h)-Thiones

Abstract

A novel synthesis of a new class of bipyridyl and biheterocyclic-nitrogen thioglycosides utilizing the reactions of heterocyclic substituted pyridine-2(1H)-thiones and alpha-bromoglucose or alpha-bromogalactose tetraacetate as starting components is described.

Thiazoles in glycosylation reactions: Novel synthesis of thiazole thioglycosides

“…[4] For this reason, many Tiazofurin analogues were synthesized aiming to produce derivatives with reduced toxicity. [5] As a part of our recent program directed toward syntheses of catabolically stable nucleoside analogues, we have recently reported on the synthesis and antiviral activity of a number of heterocyclic thioglycosides that have an interesting cytotoxic activity such as pyridine thioglycosides, [6] pyrimidine thioglycosides, [7] imidazole thioglycosides, [8] oxadiazole thioglycosides, [9] thiophene thioglycosides, [10] quinoline thioglycosides, [11] and thienopyrazole thioglycosides. [12] We have reported that the thioglycosides of dihydropyridine show a strong P-glycoprotein antagonist activity as well as against human colon carcinoma cells.…”

Synthesis and domino reactions of polymethylene‐3‐cyanopyridine‐2(1Н)‐thiones

“…[7,8,[23][24][25] In order to unambiguously establish the structures of products of these reactions, we synthesized adamantyl derivative 12 (Scheme 3) and studied it using X-ray diffraction analysis. [7,8,[23][24][25] In order to unambiguously establish the structures of products of these reactions, we synthesized adamantyl derivative 12 (Scheme 3) and studied it using X-ray diffraction analysis.…”

Synthesis of novel pyrimidine thioglycosides as structural analogs of favipiravir (avigan) and their antibird flu virus activity

“…In our previous work many antiviral heterocyclic thioglycosides were synthesized and provided an effective cytotoxicity such as imidazole thioglycosides, [9] triazole thioglycosides, [10] thiazole thioglycosides, [11] pyrazole thioglycosides, [12] pyrimidine thioglycosides, [13] pyridine thioglycosides, [14] purine thioglycosides, [15] thienopyrazole thioglycosides, [16] oxadiazole thioglycosides [17] and quinolone thioglycosides, [18] in previous work we reported that dihydropyridine thioglycosides are used as inhibitors in the protein glycosylation process. [19,20] In this work we designed a facile method for synthesis of amino pyrimidine thioglycosides compounds as Avigan analogs by the reaction of sodium 2-cyano-3-(arylamino)prop-1-ene-1,1-bis(thiolate) and guanidine hydrochloride followed by coupling of the resulting pyrimidine thiolates with a-halo sugars.…”