Synthesis and Biological Evaluation of Some Acyclic Pyridine C-Nucleosides. Part Two |
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| Authors: | Johan Van hemel Eddy L Esmans Alex De Groot Roger A Dommisse Jan M Balzarini Erik D De Clercq |
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| Institution: | 1. Nucleoside Research Unit , University of Antwerp (RUCA) , Groenenborgerlaan 171, B-2020, Antwerp, BELGIUM;2. NMR Research Unit , University of Antwerp (RUCA) , Groenenborgerlaan 171, B-2020, Antwerp, BELGIUM;3. Rega Institute for Medical Research , Katholieke Universiteit Leuven , Minderbroedersstraat 10, B-3000, Leuven, BELGIUM |
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| Abstract: | Abstract 3-Bromo-5-(2-hydroxyethylthiomethyl)pyridine (7) was synthesized by reaction of 3-bromo-5-chloromethylpyridine hydrochloride (6) with the mono sodium salt of 2-mercaptoethanol. 3-Bromo-5-hydroxymethylpyridine (10) was, after protection as a silyl ether, converted to the 3-carboxy analogue using BuLi and CO2. After deprotection with NH4F, the alcohol function was chlorinated using SOCl2. Finally, attachment of the acyclic chain and ammonolysis gave the acyclic nicotinamide nucleosides. Treatment of the latter compounds with Lawesson's reagent gave the thioamide analogues. All compounds were identified by NMR and DCI-MS. The acyclic pyridine C-nucleosides were evaluated against a series of tumor-cell lines and a variety of viruses. No marked biological activity was found. |
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