Synthesis of C-nucleosides. Part 14. 5(3)-Glycosyl-1,2,4-triazole-3(5) carboxamides as analogues of ribavirin

The Quest for an Efficacious Antiviral for Respiratory Syncytial Virus

“…The results of the foregoing study with 3-NPN were consonant with the massive volume of earlier work on the structure-activity relationships (SAR) of ribavirin and its analogues (Cook et al, 1978;De Clercq et al, 1978;Goebel et al, 1982;Huynh-Dinh et al, 1977;Kini et al, 1989;Narang & Vince, 1977;Revankar & Robins, 1975;Sanghvi et al, 1988;Sidwell et al, 1979;Smejkal et al, 1984;Srivastava et al, 1975Srivastava et al, , 1977Storer et al, 1999;Tsilevich et al, 1987;Vijayaiakshmi & Yathindra, 1980;Wood et al, 1985) Such research has demonstrated that the structural requirements for antiviral activity are quite stringent. These include an absolute requirement for the 4-carboxamido group and the probable need for an electron-rich hydrogen bond acceptor corresponding to the 5 position of the triazole ring of ribavirin.…”

1,2,4-Triazoles: Synthetic approaches and pharmacological importance. (Review)

“…Al-Masoudi et al [113] have used the cycloaddition of cations 83 with sugar nitriles as a novel method to prepare the C-nucleosides, since a few 1,2,4-triazole C-ribonucleosides were prepared [114][115][116][117][118][119]. Thus, cycloaddition of the peracylated β-D-ribofuranosyl nitrile 86 [120] with 83a-c, formed from (chloroalkyl)azo compounds 82 in the presence of SbCl 5 , afforded iminium salts 87a-c.…”

A New 1,2,4-Triazole Acyclonucleosides: Synthesis and Biological Evaluation

“…The preparation by direct method of a five-member-ring 3-methoxycarbonyl-5-methyl-1,2,4-triazole 1 (Scheme 1) from the condensation in pyridine between hydrochlorated acetamidine [12] and methyl hydrazidooxalate [13] has been already reported [14] in the literature. The synthetic route for the preparation of acyclic nucleoside analogues is outlined in Scheme 2.…”