Synthesis of 2′-deoxy-5-fluoro-5′-O-1″,3″,2″-oxazaphosphacyclohexa-2″-yluridine 2″-oxide and related compounds
- 1 January 1980
- journal article
- Published by Elsevier BV in Tetrahedron
- Vol. 36 (16), 2337-2340
- https://doi.org/10.1016/0040-4020(80)80130-x
Abstract
2′,3′- O-Isopropylidene -5′- O -1″,3″,2″- oxazaphosphacyclohex -2″- yl-uridine 2″- oxide has been obtained by the action of phosphoryl chloride and N-methylmorpholine, followed by 3-aminopropan-1-ol, on 2',3'-O-isopropy-lidineuridine. A similar reaction carried out on 3'-O-acetylthymidine, followed by removal of the acetyl group gave 5′-O-1″,3″,2″- oxazaphospha -2″- yl-thymidine 2″- oxide . Both of these compounds were obtained more conveniently by treatment of 2',3'-O-isopropylideneuridine and thymidine respectively with 2-chloro-1,3,2-oxazaphosphacyclo-hexane 2-oxide in pyridine. Similar treatment of 2′-deoxy-5-fluorouridine gave 2′-deoxy-5-fluoro-5′-O-1″,3″,2″- oxazaphosphacyclohex -2″- yluridine 2″- oxide . The latter compound was tested for activity against S 180 Crocker sarcoma and L 1210 mouse leukaemia. Only a marginal activity against the S 180 sarcoma was detected. However inactivity of the compound in inducing leukopenia indicated that it might be of low toxicity and that further testing of the compound would be justified.Keywords
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