- REACTION OF NUCLEOSIDES WITH THIONYL CHLORIDE; PREPARATION OF THE DEOXY DERIVATIVES OF CYTIDINE AND ADENOSINE
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On reaction of thionyl chloride with cytidine and adenosine in refluxing acetonitrile, the 5'-chloro-2',3'-sulphinyl derivatives I and VII are formed in a quantitative yield.On heating in dimethylformamide, compound I affords 5'-chloro-5'-deoxycyclocytidine (II) which is hydrolyzed in alkali to the arabinosyl derivative III; reduction of III with tributyltin hydride gives the 5'-deoxyarabinosyl derivative IV.The sulphinyl derivative I is hydrolyzed to 5'-chloro-5'-deoxycytidine (V) which is reduced to 5'-deoxycytidine (VI).Analogously, the sulphinyl derivative VII affords 5'-chloro-5'-deoxyadenosine (VIII) and the reduction of VIII gives 5'-deoxyadenosine (IX).Of these compounds, the 5'-chloro-5'-deoxyarabinosyl derivative as the only one shows an inhibitory effect towards the L1210 cell growth.
- Hrebabecky, Hubert,Brokes, Josef,Beranek, Jiri
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p. 599 - 605
(2007/10/02)
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