Synthesis and anti-HSV-1 activity of new 1,2,3-triazole derivatives

Abstract

In this work, a new series of arysulfonylhydrazine-1H-1,2,3-triazole derivatives were synthesized, and their ability to inhibit the in vitro replication of HSV-1 was evaluated. Among the 1,2,3-triazole derivatives, 1-[(5″-methyl-1″-(4‴-fluorophenylamino)-1H-1,2,3-triazol-4″-yl)carbonyl]-2-(4'-methylphenylsulfonyl)hydrazine and 1-[(5'-methyl-1'-(2″,5″-dichlorophenylamino)-1H-1,2,3-triazol-4'-yl)carbonyl]-2-(phenylsulfonyl)hydrazine, with IC(50) values of 1.30 and 1.26 μM, respectively, displayed potent activity against HSV-1. Because these compounds have low cytotoxicity, their selectivity indices are high. Under the assay conditions, they have better performance than does the reference compound acyclovir. The structures of all of the compounds were confirmed by one- and two-dimensional NMR techniques ((1)H, (13)C-APT, COSY-(1)H×(1)H and HETCOR (1)J(CH)) and by elemental analysis.

Microwave-Assisted Synthesis, Characterization, and Biological Evaluation of Phenylacrylamide Derivatives of Triazoles Derived From Oxazolones

“…Triazole moiety may be considered as a bioisostere of imidazole, which is a part of the azole group of antifungal drug (i.e., fluconazole). The 1, 2, 4-triazole nucleus has been incorporated into a wide variety of therapeutically important agents such as ribavirin (antiviral), rizatriptan (antimigraine), alprazolam (anxiolytic), vorozole, letrozole, and anastrozole (antitumoral) [11][12][13][14][15][16][17][18][19][20][21][22][23].…”

Structures of 1-(substituted-phenyl)-4-hydroxymethyl- and -4-fluoromethyl-1,2,3-triazoles

“…Boechat and co-workers [3][4][5][6][7] and other Rio de Janeiro based groups [8,9] have been interested in the synthesis, biological activities and crystal structures of 1,2,3-triazole derivatives for some time.…”

Antivenom Effects of 1,2,3-Triazoles againstBothrops jararacaandLachesis mutaSnakes

“…Literature has described 1,2,3-triazole compound as an important class of five-member nitrogen heterocyclic system which exhibits different pharmacological profiles, such as antiplatelet activity [15], anticlotting [16], antiviral [17], trypanocidal [18], antimicrobial [19], and/or their use in treating schizophrenia [20] and leishmaniasis [21]. Two general methods are available for the construction of 1,2,3-triazole rings: Huisgen 1,3-dipolar cycloaddition reactions [22], in particular the copper(I)-catalyzed cycloaddition [23], and the intramolecular 1,5-electrocyclization of β -substituted- α -diazocarbonyl compounds [24]. Our previous studies have indicated that six new synthetic 1,2,3-triazole compounds (1-arylsulfonylamino-5-methyl-1 H -[1,2, 3]-triazole-4-carboxylic acid ethyl esters) inhibited the hemolysis induced by L. muta venom [25].…”