Synthesis of Substituted-Benzyl and Sugar-Modified Analogues of 6-N-(4-Nitrobenzyl)adenosine and Their Interactions with “ES” Nucleoside Transport Systems

Morris J. Robins Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada, T6G 2H7; Department of Chemistry, Brigham Young University, Provo, UT, 84602, U.S.A.

Jun-ichi Asakura Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada, T6G 2H7; Department of Chemistry, Brigham Young University, Provo, UT, 84602, U.S.A.

Masakatsu Kaneko Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada, T6G 2H7

Susumu Shibuya Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada, T6G 2H7

Ewa S. Jakobs Department of McEachern Laboratory, University of Alberta, Edmonton, Alberta, Canada, T6G 2H7

Francisca R. Agbanyo Department of McEachern Laboratory, University of Alberta, Edmonton, Alberta, Canada, T6G 2H7

Carol E. Cass Department of Biochemistry, University of Alberta, Edmonton, Alberta, Canada, T6G 2H7; Department of McEachern Laboratory, University of Alberta, Edmonton, Alberta, Canada, T6G 2H7

Alan R. P. Paterson Department of Pharmacology, University of Alberta, Edmonton, Alberta, Canada, T6G 2H7; Department of McEachern Laboratory, University of Alberta, Edmonton, Alberta, Canada, T6G 2H7

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Abstract

Four classes of 6-X-benzylated purine nucleosides, (i) 6-N-(substituted-benzyl)adenosines, (ii) 6-N-(4-nitrobenzyl)adenine nucleosides with modified sugars, (iii) 6-N(S)-(4-azidobenzyl) derivatives of adenosine, 6-thioinosine, and 6-thioguanosine, and (iv) 6-N-{4-N-[acyl(sulfonyl)amino]benzyl}adenosines, were synthesized and their binding interactions with “es-NT” ( e quilibrative, inhibitor-sensitive nucleoside transport) systems were studied. Several tight-binding analogues were found.

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Synthesis of Substituted-Benzyl and Sugar-Modified Analogues of 6-N-(4-Nitrobenzyl)adenosine and Their Interactions with “ES” Nucleoside Transport Systems

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Synthesis of Substituted-Benzyl and Sugar-Modified Analogues of 6-N-(4-Nitrobenzyl)adenosine and Their Interactions with “ES” Nucleoside Transport Systems

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