Synthesis and Antiviral (RNA) Evaluation of Nucleoside Analogs of Tiazofurin Modified at the Carboxamide Moiety

Michael J. Phelan U.S. Army Medical Research Institute of Infectious Diseases, Fort Detrick, Frederick, Maryland, 21702

Bjarne Gabrielsen U.S. Army Medical Research Institute of Infectious Diseases, Fort Detrick, Frederick, Maryland, 21702

Jorma J. Kirsi Southern Research Institute, Virology Division, Birmingham, Alabama, 35255

William M. Shannon Southern Research Institute, Virology Division, Birmingham, Alabama, 35255

Michael A. Ussery Food and Drug Administration, Rockville, Maryland, 20855

Louis Barthel-Rosa Department of Chemistry, University of Nevada-Reno, Reno, Nevada, 89557

Ernst M. Schubert Pharm-Eco Laboratories, Inc., Lexington, Massachusetts, 02173

Ganesh D. Kini School of Medicine, Univ. of California - San Diego, La Jolla, California, 92093

Roland K. Robins U.S. Army Medical Research Institute of Infectious Diseases, Fort Detrick, Frederick, Maryland, 21702

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Abstract

The carboxamide functionality of tiazofurin 1a has been modified to produce the following analogs: carboximidates 5a,b, carboxamidines 6, 10, tetrahydropyrimidine 7, N-glycine 8 and N-glutamine 9. These structural modifications abolished the in vitro antiviral (RNA) activity exhibited by tiazofurin against the flaviviruses (yellow fever and Japanese encephalitis viruses), bunyavirus (Punta Toro virus) and togavirus (Venezuelan equine encephalomyelitis virus). Only carboximidates 5a,b retained marginal activity against bunyaviruses.

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Synthesis and Antiviral (RNA) Evaluation of Nucleoside Analogs of Tiazofurin Modified at the Carboxamide Moiety

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Synthesis and Antiviral (RNA) Evaluation of Nucleoside Analogs of Tiazofurin Modified at the Carboxamide Moiety

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