AN EPIMER OF 5'-NORARISTEROMYCIN AND ITS ANTIVIRAL PROPERTIES

A derivative of 5'-noraristeromycin epimeric at the 5'-nor center ((-) -3) has been prepared enantiospecifically in three steps from (+)-((1R ,4S)-4-hydroxy-2-cyclopenten-1-yl acetate. Compound (-)-3 was evaluate d for antiviral activity against a large number of viruses and found t o display marked activity against varicella-zoster virus, vaccinia vir us, vesicular stomatitis virus, parainfluenza virus, reovirus,and cyto megalovirus. A similar antiviral activity spectrum was Shown by the S- adenosylhomocysteine hydrolase inhibitors neplanocin A and carbocyclic 3-deazaadenosine. While equally potent as neplanocin A against most o f the viruses tested, compound (-)-3 was significantly less cytotoxic. The results of this study suggest that (-)-3 should be pursued for th e treatment of those virus infections [that is, pox (VV);rhabdo (VSV), paramyxo (parainfluenza), and reo] that appear to be exquisitively se nsitive to the compound.