| Popis: |
The synthesis of the title compound (15) and its 1'-fluoro (12) and 1'-hydroxy (12) derivatives is described. Key intermediate 4-chloro- 1-[1,2-dihydroxy-1,2-O-(ethoxymethylene)-3-nonyl]imidazo[4,5-c]pyridine (10) was obtained by two routes through condensation of (2R,3R)-3-amino- 1,2-O-isopropylidene-1,2-nonanediol (3) with either 2,4-dichloro- or 4-chloro-3-nitropyridine. When assayed as adenosine deaminase inhibi- tors, (15) was found to be almost twice as active as its racemate. While hydroxylation at the 1'-position resulted in an 80-fold decrease in activity, the 1'-fluoro derivative proved to have activity comparable to that of 3-deaza-(+)-EHNA |
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