1222521-18-7Relevant articles and documents
5′-silylated 3′-1,2,3-triazolyl thymidine analogues as inhibitors of West Nile Virus and Dengue virus
Vernekar, Sanjeev Kumar V.,Qiu, Li,Zhang, Jing,Kankanala, Jayakanth,Li, Hongmin,Geraghty, Robert J.,Wang, Zhengqiang
supporting information, p. 4016 - 4028 (2015/05/27)
West Nile virus (WNV) and Dengue virus (DENV) are important human pathogens for which there are presently no vaccine or specific antivirals. We report herein a 5′-silylated nucleoside scaffold derived from 3′-azidothymidine (AZT) consistently and selectively inhibiting WNV and DENV at low micromolar concentrations. Further synthesis of various triazole bioisosteres demonstrated clear structure-activity relationships (SARs) in which the antiviral activity against WNV and DENV hinges largely on both the 5′-silyl group and the substituent of 3′-triazole or its bioisosteres. Particularly interesting is the 5′ silyl group which turns on the antiviral activity against WNV and DENV while abrogating the previously reported antiviral potency against human immunodeficiency virus (HIV-1). The antiviral activity was confirmed through a plaque assay where viral titer reduction was observed in the presence of selected compounds. Molecular modeling and competitive S-adenosyl-l-methionine (SAM) binding assay suggest that these compounds likely confer antiviral activity via binding to methyltransferase (MTase).
Straightforward carbamoylation of nucleophilic compounds employing organic azides, phosphines, and aqueous trialkylammonium hydrogen carbonate
Yagodkin, Andrey,L?schcke, Kerstin,Weisell, Janne,Azhayev, Alex
experimental part, p. 2210 - 2221 (2010/04/29)
In the presence of aqueous trialkylammonium hydrogen carbonate, the Staudinger reaction leads to the intermediate formation of the corresponding isocyanate, which, in turn, reacts further with a nucleophilic reagent also present in the mixture and results in carbamoylation with good yield. On the basis of this reaction a practical carbamoylation procedure was devised and a comparative study on suitability of different solvents and phosphorus (III) derivatives for carbamoylation reaction was conducted. The versatility of the method was demonstrated by examples with different classes of nucleophilic compounds that included the aminomethyl resin and natural compounds that display poor solubility in organic solvents.
