Synthetic Studies on the Isomeric N -Methyl Derivatives of C-Ribavirin |
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| Authors: | Giin-Yuan Shen Roland K Robins Ganapathi R Revankar |
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| Institution: | 1. Department of Medicinal Chemistry , Nucleic Acid Research Institute , 3300 Hyland Avenue, Costa Mesa, California, 92626, U. S. A.;2. Pharm-Eco Laboratories, Inc. , 2355 Chain Drive, Simi Valley, CA, 93085;3. Department of Medicinal Chemistry , Nucleic Acid Research Institute , 3300 Hyland Avenue, Costa Mesa, California, 92626, U. S. A.;4. Triplex Pharmaceuticals Corp. , 9391 Grogans Mill Rd., The Woodlands, TX, 77380 |
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| Abstract: | Abstract The syntheses of all three of the mono-N-methy1 derivatives of C-ribavirin (3-β-D-ribofuranosyl-1, 2, 4-triazole-5-carboxamide, 2) have been accomplished. Reaction of 1-(β-D-ribofuranosyliminomethyl)-2-methyl-hydrazine ( 7 ) with ethyl oxamate (8) in boiling ethanol gave the N′-methyl-C-ribavirin ( 3 ). A similar treatment of β-D-ribofuranosyl-1-carboximidic acid methyl ester ( 6 ) with N′-methyloxamic hydrazide ( 10 ) furnished the N2-methyl-C-ribavirin ( 4 ). Direct methylation of unprotected 2 with methyl iodide in the presence of potassium carbonate in dimethyl sulfoxide gave N 4-methyl isomer ( 5 ) as the major product. Structural assignments of 3 , 4 , and 5 were based on the unequivocal synthetic sequences, 1H and 13C NMR data and confirmed by single crystal X-ray diffraction analysis. |
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