96865-87-1Relevant academic research and scientific papers
Xanthine Functionalized Congeners as Potent Ligands at A2-Adenosine Receptors
Jacobson, Kenneth A.,Ukena, Dieter,Padgett, William,Daly, John W.,Kirk, Kenneth L.
, p. 211 - 214 (2007/10/02)
Amide derivatives of a carboxylic acid congener of 1,3-dialkylxanthine, having a 4-phenyl substituent at the 8-position, have been synthesized in order to identify potent antagonists at A2-adenosine receptors stimulatory to
BIOLOGICALLY-ACTIVE 1,3-DIPROPYL-8-PHENYLXANTHINE DERIVATIVES
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, (2008/06/13)
Certain functionalized congeners of 1,3-dialkylxanthine exhibit high potency and selectivity as antagonists for A 1-and A. sub.2-adenosine receptors and are suitable for attachment to probes, drug carriers, or solid supports. These derivatives are characterized by the presence of a phenyl at the 8 position para-substituted with a functionalized chain to provide high water solubility and high receptor affinity to such an extent that these compounds are suitable for use as antiallergenic, antiasthmatic, or cardiotonic drugs, central nervous system stimulants, and diuretics.
Functionalized Congeners of 1,3-Dialkylxanthines: Preparation of Analogues with High Affinity for Adenosine Receptors
Jacobson, Kenneth A.,Kirk, Kenneth L.,Padgett, William L.,Daly, John W.
, p. 1334 - 1340 (2007/10/02)
A series of functionalized congeners of 1,3-dialkylxanthines has been prepared as adenosine receptor antagonists.On the basis of high potency of 8-(p-hydroxyphenyl)-1,3-dialkylxanthines, the parent compounds were 8-phenyl> derivatives of theophylline and 1,3-dipropylxanthine.A series of analogues including esters of ethanol and N-hydroxysuccinimide, amides, a hydrazide, an acylurea, and anilides were prepared.The potency in blocking A1-adenosine receptors (inhibition of binding of N6-cyclohexyladenosine to brain membranes) and A2-adenosine receptors (inhibition of 2-chloroadenosine-elicited accumulations of cyclic AMP in brain slices) was markedly affected by structural changes distal to the primary pharmacophore (8-phenyl-1,3-dialkylxanthine).Potencies in the dipropyl series at the A1 receptor ranged from Ki values of 1.2 nM for a congener with a terminal amidoethyleneamine moiety to a Ki value of 58 nM for the parent carboxylic acid to a Ki of 96 nM for the bulky ureido congener.Certain congeners were up to 145-fold more active at A1 receptors than at A2 receptors.Various derivatives of the congeners should be useful as receptor probes and for radioidodination, avidin binding, and preparation of affinity columns.
