59119-48-1Relevant academic research and scientific papers
1,3-Dialkyl-8-(hetero)aryl-9-OH-9-deazaxanthines as potent A2B adenosine receptor antagonists: Design, synthesis, structure-affinity and structure-selectivity relationships
Stefanachi, Angela,Nicolotti, Orazio,Leonetti, Francesco,Cellamare, Saverio,Campagna, Francesco,Loza, Maria Isabel,Brea, Jose Manuel,Mazza, Fernando,Gavuzzo, Enrico,Carotti, Angelo
experimental part, p. 9780 - 9789 (2009/04/11)
A number of 1,3-dialkyl-8-(hetero)aryl-9-OH-9-deazaxanthines were prepared and evaluated as ligands of recombinant human adenosine receptors (hARs). Several 1,3-dipropyl derivatives endowed with nanomolar binding affinity at hA2B receptors, but poor selectivity over hA2A, hA1 and hA3 AR subtypes were identified. A comparison with the corresponding 7-OH- and 7,9-unsubstituted-deazaxanthines revealed that 9-OH-9-deazaxanthines are more potent hA2B ligands with lower partition coefficients and higher water solubility compared to the other two congeneric classes of deazaxanthines. An optimization of the para-substituent of the 8-phenyl ring of 9-OH-9-deazaxanthines led to the discovery of compound 38, which exhibited outstanding hA2B affinity (Ki = 1.0 nM), good selectivity over hA2A, hA1 and hA3 (selectivity indices = 100, 79 and 1290, respectively) and excellent antagonist potency in a functional assay on rat A2B (pA2B = 9.33).
NEW SYNTHESIS OF 1,3-DIMETHYL-7-HYDROXYPYRROLOPYRIMIDINE-2,4(1H,3H)-DIONES (9-HYDROXY-9-DEAZATHEOPHYLLINES)
Yoneda, Fumio,Motokura, Miyuki,Otagiri, Masaki
, p. 1273 - 1276 (2007/10/02)
Treatment of 5-nitro-1,3,6-trinitrouracil with aryl aldehydes in the presence of piperidine causes the condensation to the 5-nitro-6-styryl-uracil derivatives, followed by the intramolecular cyclization including piperidine-catalyzed oxidation-reduction t
