A convenient new synthesis, characterization and antibacterial activity of double headed acyclo-C-nucleosides from unprotected d-glucose

Double-headed nucleosides: Synthesis and applications

“…Among the tested compound, derivative 235 showed fair activity against E. coli and C. albicans but was inactive against S. aureus whereas compound 234 showed activity only against S. aureus [19]. Amara and Othman [20] synthesized the double-headed acyclo-C-nucleosides 1,4-bis(3-mercapto-1H-1,2,4-triazol-5-yl)butane- The double-headed C-nucleosides 240-242 were tested in vitro against Gram-positive bacteria Staphylococcus aureus, Listeria inovanii and Gram-negative bacteria Klebsiella pneumoniae, Salmonella sp., and Escherichia coli. All the double-headed nucleosides except derivative 242 showed moderate antibacterial activity in comparison with the known antibiotic combination amoxicillin/clavulanic acid (AMC) [20].…”

“…On the other hand, a variety of heterocyclic/carbocyclic moieties were considered as the head of these modified nucleosides. The heterocyclic structures which were found to be attached to these double-headed nucleosides include triazolophthalazine [11], 4,6-di-tert-butylbenzoxazole [12], mesitylisoxazole [13], 5-trimethylsilyl-1,2,3-triazole [14], 1-pivaloyloxymethyl-1H-1,2,3-triazole [15], 1,3,4-oxadiazino [6,5-b]indole [16], 6,7-dihydro-6-oxo-5H-1,2,4triazolo [3,4-b][1, 3,4]thiadiazine [17], 1,2,4-triazino [5,6b]indole [18], 1,3,4-thiadiazoline [19], 1,3,4-oxadiazoline [19], 1,2,4-triazoline [19], 3-mercapto-1H-1,2,4-triazole [20], 1,3,4oxadiazole-2(3H)-thione [20], 4-amino-5-mercapto-4H-1,2,4triazole [20], and 1,2,4-triazolo [3,4-b](1,3,4)-thiadiazole moieties [21]. Additionally, selected examples of doubleheaded nucleosides comprising aromatic/polyaromatic/carbocyclic moieties such as phenyl [13][14][15]22], pyrene [23][24][25], adamant-1-yl [24], cholesteryl [24], perylen-3-yl [24], 4-(tertbutyldimethylsilyloxy/hydroxy)phenyl [26], 3/4-(N-((dimethylamino)methy-lidene)aminosulfonyl)phenyl [26,27], and sulfonamido-substituted benzothiazole [28] attached as an additional head are also reported in this review article.…”

Two decades of the synthesis of mono- and bis-aminomercapto[1,2,4]triazoles

“…1 In addition, the same procedure (alcoholic hydrazine solution) was applied to the conversion of 1,4-bis(2-mercapto-1,3,4oxadiazol-5-yl)butane-1,2,3,4-tetrol (48) to 1,4-bis(4-amino-5mercapto-4H-1,2,4-triazol-3-yl)butane-1,2,3,4-tetrol (49) (Scheme 18). 143 4-Amino-5-mercapto[1,2,4]triazole 1 and its 3-substituted derivatives 2-4 (Chart 2) contain both amino and mercapto groups as ready-made nucleophilic centers for the synthesis of condensed heterocyclic rings.…”

DFT Studies of New Class of Single-Headed Nucleosides Derived from the D-glucaric Acid

“…However, we have selected three, which are : the 1,3,4-oxadiazole-2thione (5), the 1,2,4-triazole-3-thiol (6) and the 4-amino-1,2,4-triazole-3-thiol (7), whose structures are given in the figure 2. This choice is justified by the fact that three double-headed acyclo-C-nucleosides, carriers these heterocycles, were synthesized from the D-glucaric acid (1) (Amara and Othman, 2016) and whose computational results have already been published (Amara et al, 2015). So, this is continuity in the path of a series of molecules already synthesized.…”