Reference

Halogenated pyrrolopyrimidine analogs of adenosine from marine organisms: pharmacological activities and potent inhibition of adenosine kinase

Halogenated pyrrolopyrimidine analogs of adenosine from marine organisms: pharmacological activities and potent inhibition of adenosine kinase. Davies, Les P.; Jamieson, Dana D.; Baird-Lambert, Judith A.; Kazlauskas, Rymantas (Roche Res. Inst. Marine Pharmacol., Dee Why, Australia). Biochem. Pharmacol., 33(3), 347-55 (English) 1984. CODEN: BCPCA6. ISSN: 0006-2952. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacology) Two novel halogenated pyrrolopyrimidine analogs of adenosine, isolated from marine sources, were examd. for pharmacol. and biochem. activities. 4-Amino-5-bromopyrrolo[2,3-d]pyrimidine (I) [22276-99-9], from a sponge of the genus Echinodictyum, had bronchodilator activity at least as potent as theophylline but with a different biochem. profile; unlike theophylline it had no antagonist activity at central adenosine [58-61-7] receptors and it was quite a potent inhibitor of adenosine uptake and adenosine kinase [9027-72-9] in brain tissue. 5'-Deoxy-5-iodotubercidin (II) [85209-84-3], isolated from the red alga Hypnea valentiae, caused potent muscle relaxation and hypothermia when injected into mice. This compd. was a very potent inhibitor of adenosine uptake into rat and guinea pig brain slices and an extremely potent inhibitor of adenosine kinase from guinea pig brain and rat brain and liver. Neither of these 2 pyrrolopyrimidine analogs was a substrate for, or an inhibitor of, adenosine deaminase [9026-93-1]. 58-61-7 and 22276-99-9 which are cas registry numbers of substances are two of reagents here. Neither compd. appeared to have any direct agonist activity on guinea pig brain adenosine-stimulated adenylate cyclase (A2 adenosine receptors). 5'-Deoxy-5-iodotubercidin is unique in 2 respects: it appears to be the first naturally-occurring example of a 5'-deoxyribosyl nucleoside and is the first example of a specifically iodinated nucleoside from natural sources. It may be the most potent adenosine kinase inhibitor yet described and, by virtue of its structure, may prove to be the most specific. .