- BICYCLIC HETEROCYCLES, METHOD FOR PRODUCING THEM AND THEIR USE AS HERBICIDES AND PHARMACEUTICAL AGENTS
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Methods and compounds for inhibiting the enzymes adenosine monophosphate deaminase or adenoside deaminase are provided. Such methods and compounds are useful in agriculture, horticulture and/or pharmacology as, for example, active compounds for crop prote
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Page/Page column 34; 35
(2008/06/13)
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- Synthesis of C-ribosyl imidazo[2,1-f][1,2,4]triazines as inhibitors of adenosine and AMP deaminases
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The 3-β-D-ribofuranoside 6 of the new imidazo[2,1-f][1,2,4]triazine 27 is isomeric and isoelectronic with the nucleoside deaminoformycin 1 which is a good inhibitor of adenosine deaminase (ADA) while its 5′-monophosphate 2 is a good inhibitor of adenosine 5′-monophosphate deaminase (AMPDA). The 6-methylsulfanyl derivative 7 of 6 is synthesized by condensation of the monocyclic 1,2,4-triazine 9 with bromo aldehyde 10, which is accompanied by cyclization to give the protected C-nucleoside 21; the 8-methylsulfanyl group of 21 is removed by replacement by hydrazine and oxidation. The 1,2,4-triazine 9 cyclizes similarly with chloroacetaldehyde or its dimethyl acetal to give 6,8-bis(methylsulfanyl)imidazo[2,1-f][1,2,4]triazine 17, which is converted into the parent heterocycle 27 by two routes, and into mono- and di-substituted derivatives (19, 20, 24, 25, 28-30) of the new ring system. Riboside 7 is an inhibitor of mammalian ADA (IC50 40 μM). The Royal Society of Chemistry 1999.
- Dudfield, Philip J.,Le, Van-Due,Lindell, Stephen D.,Rees, Charles W.
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p. 2929 - 2936
(2007/10/03)
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