2005
DOI: 10.1021/jm050792d
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2-(Benzimidazol-2-yl)quinoxalines:  A Novel Class of Selective Antagonists at Human A1and A3Adenosine Receptors Designed by 3D Database Searching

Abstract: The Cambridge Structural Database (CSD) was searched through two 3D queries based on substructures shared by well-known antagonists at the A(1) and A(3) adenosine receptors (ARs). Among the resulting 557 hits found in the CSD, we selected five compounds to purchase, synthesize, or translate synthetically into analogues better tailored to interact with the biological targets. Binding experiments using human ARs showed that four out of five tested compounds turned out to be antagonists at the A(1)AR or A(3)AR wi… Show more

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Cited by 47 publications
(46 citation statements)
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“…Another class of bicyclic scaffold derivatives, the quinazoline derivatives (compounds 136, 137 ) and quinoxaline derivative (compound 138 ) are also derived from the in silico molecular simplification of the triazoloquinoxalinone (TQX) scaffold. They are discussed in more details under Section ,D …”
Section: Medicinal Chemistry Of A3ar Ligandsmentioning
confidence: 99%
“…Another class of bicyclic scaffold derivatives, the quinazoline derivatives (compounds 136, 137 ) and quinoxaline derivative (compound 138 ) are also derived from the in silico molecular simplification of the triazoloquinoxalinone (TQX) scaffold. They are discussed in more details under Section ,D …”
Section: Medicinal Chemistry Of A3ar Ligandsmentioning
confidence: 99%
“…The quinoxaline derivative 64 (Fig. 9) deserves to be mentioned here, not only because of its good binding profile as an A 3 AR antagonist, but also (especially) due to the novelty of the strategy applied to its design, which was based on a 3D database-searching approach (Novellino et al 2005). There is increasing evidence of the importance of 2D/3D database searching as a valuable tool to discover novel lead compounds for the A 3 AR and for other G-protein-coupled receptors (GPCRs) (Costanzi et al 2008).…”
Section: A3ar Antagonistsmentioning
confidence: 99%
“…[23] Scheme 7. Proposed benzimidazoylquinoxalines (3) synthesis mechanism from 1,2-phenylenediamine derivatives (1) and glyceraldehyde (10).…”
Section: Scope Of the Reactionmentioning
confidence: 99%
“…[9] Benzymidazoylquinoxaline compounds have shown properties as a novel class of selective antagonists at human A1 and A3 adenosine receptors. [10] Methods for the synthesis of these heteroarylquinoxalines are limited. An option involves the reaction of the corresponding o-phenylenediamine derivative with 3-hydroxyimino-2-butanone and bromine in a one-pot reaction (Scheme 1).…”
Section: Introductionmentioning
confidence: 99%