Studies on the synthesis of compounds related to adenosine 3',5'-cyclic phosphate. III. The synthesis of 2-halogenoadenosine 3',5'-cyclic phosphate.
- 1 January 1978
- journal article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 26 (8) , 2391-2395
- https://doi.org/10.1248/cpb.26.2391
Abstract
Because of the presence of etheno group, the reactivity of mercapto residue at 2 position in purine skeleton is so high that 2-chloro-1, N6-etheno adenosine 3', 5'-cyclic phosphate (2-chloro-1, N6-etheno c-AMP) and 2-iodo-1, N6-etheno c-AMP were easily synthesized from 2-mercapto-1, N6-etheno c-AMP. The deblocking reaction of the etheno group from these two halogenated products with N-bromosuccinimide (NBS) gave 2-chloro-c-AMP and 2-iodo-c-AMP. When 2-amino-c-AMP, which was synthesized from 2-amino-1, N6-etheno c-AMP by the same deblocking reaction, was diazotized with sodium nitrite in 42% fluoroboric acid (HBF4) at -10--20°, 2-fluoro-c-AMP was obtained in a yield of 17.8%. Since 2-bromo-c-AMP has been similarly obtained in previous work, the deblocking reaction of etheno group offers an excellent new route to synthesis of 2-halogeno-c-AMPs from c-AMP.Keywords
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