Antiviral Activity of Benzotriazole Based Derivatives

Abstract

Background: For the last thirty years, the benzotriazole scaffold has been the object of our group interest and we have already presented some results on the antiviral activity of our compounds. Objective: In this article, we conclude the exploration of N-(4-(R-2H-benzo[d][1,2,3]triazol-2-yl)phenyl)-4-R’-benzamides and 1-(4-(R-2H-benzo[d][1,2,3]triazol-2-yl)phenyl)-3-R’-ureas by synthesizing further modified derivatives, in order to have more elements for SARs evaluation. Methods: Here, we reported the synthesis and the antiviral screening results of 38 newly synthesized benzotriazole derivatives against a panel of DNA and RNA viruses. We also analyse SARs in comparing these compounds with previously published benzotriazole analogues, taking stock of the situation. Results: Among the newly presented derivatives, compounds 17 and 18 were the most active with EC50 6.9 and 5.5 µM, respectively against Coxsackievirus B5 (CV-B5) and 20.5 and 17.5 µM against Poliovirus (Sb-1). Conclusion: we can conclude that N-(4-(2H-benzo[d] [1 - 3] triazol-2-yl)phenyl-R-amide is a good chemical scaffold for the development of new antiviral molecules.

Design, Synthesis, Antimicrobial Evaluation of Novel 2‐Oxo‐4‐Substituted Aryl‐Azetidine Benzotriazole Derivatives**

“…Equal quantity of octanol and water (10 ml) containing 5 mg sample was combined in a graduated glass tube with a glass stopper. After being thoroughly stirred for 24 h with the aid of a mechanical stirrer, the mixture was left to isolate into its different phases for 6 h. After separation of phases, filter using membrane filter, and drug content analyzed in the aqueous phase using UV spectroscopy [37,38] . Experimental and theoretical values of log p given in Table 5.…”

Design, Synthesis, and Antiviral Activities of New Benzotriazole-Based Derivatives

“… General structures of our benzotriazole-based antiviral compounds: series ( A ), active against CVB (EC 50 values between 8–10 µM) and RSV (EC 50 values 3–7 µM). Series ( B ), active on HTNV (EC 50 < 5 µM), CVB (EC 50 values between 4–8 µM) and RSV (EC 50 values 2–3 µM) [ 51 , 52 , 53 , 54 ]. …”

“…We previously reported different generations of BTZ-based compounds variously functionalized to exert in turn selective or wide-spectrum antiviral activity [ 51 , 52 , 53 , 54 ]. By screening the synthesized compounds on a panel of viruses, including representative pathogens of the Flaviviridae , Picornaviridae , Reoviridae , Rhabdoviridae , Paramyxoviridae , Poxviridae , and Herpesviridae families, we identified a number of hit compounds, whose general structures are active against three viral strains, as depicted in Figure 2 : Coxsackievirus B (CVB) [ 51 , 53 ], respiratory syncytial virus (RSV) [ 54 ] and Orthohantavirus (HTNV) [ 52 ].…”

Main and by-processes at 1-(2-nitroaryl)-1H-benzotriazole reduction

“…Further, we studied the impact of this factor on the 1(2-nitroaryl)-1Hbenzotriazoles reduction. The choice of these substrates is due to resulting N-(aminoaryl)benzotriazole derivatives are widely used in drug development [4][5][6][7]. Also, isomerization process can be expected to occur during the reduction.…”