ChemInform Abstract: Substituted 1,2,3‐Triazolo[1,5‐a]quinazolines: Synthesis and Binding to Benzodiazepine and Adenosine Receptors.

Abstract

Substituted 1,2,3-Triazolo[1,5-a]quinazolines: Synthesis and Binding to Benzodiazepine and Adenosine Receptors. -Cyclization reactions and nucleophilic displacement are carried out to form new title compounds, e.g. (V), (VIII), and (XI). These compounds show decreased activity compared to triazoloquinazoline derivatives. The most potent compounds within this study are found to be the derivatives (VIII) and (XI). -(BERTELLI,

A New Series of 2-Alkoxy(aralkoxy)-[1,2,4]triazolo[1,5-a]quinazolin-5-ones as Adenosine Receptor Antagonists

“…48,49) Within our work, conversion of the lactam moiety in 1a, b, d into an imidoyl chloride function 6a-c has not influenced positively effects on the affinity profiles towards A 1 and A 2A . However, compounds 6a, c have emerged almost the same behavior in the terms of affinity at A 1 subtype (4, 6.8 mM) with their parent compounds 1a, d (4.25, 6.8 mM), whereas 6b was less potent than 1b.…”

One‐Pot Synthesis of Triazoloquinazolinones via Copper‐ Catalyzed Tandem Click and Intramolecular CH Amidation

“…and diisoproylethylamine (DIPEA) (1.2 equiv.) in the presence of CuI (10 mol%) in THF under air at room temperature for 1 h delivered the cyclized product 3aa in 80% yield ( 14).…”

“…These tricyclic heterocycles show moderate affinity towards benzodiazepine receptors, A 1 and A 2A adenosine receptors and they can act as ligands against GABA A receptors. [11][12][13][14] Additionally, the 1,2,3-triazole core is a prominent structural motif in medicinal chemistry and is frequently found in medicinally important compounds. [15] Given the prevalence of this privileged core in biologically active molecules, it has received relatively less atten-tion so far and the direct synthetic methods available in the literature are very limited.…”

“…Triazoloquinazolinones are an important class of nitrogen‐containing heterocycles which exhibit a wide range of biological applications such as anticancer and antihypertensive agents. These tricyclic heterocycles show moderate affinity towards benzodiazepine receptors, A 1 and A 2A adenosine receptors and they can act as ligands against GABA A receptors 11–14. Additionally, the 1,2,3‐triazole core is a prominent structural motif in medicinal chemistry and is frequently found in medicinally important compounds 15.…”

Condensed 1,2,3-triazoles (review)

“…Triazoles condensed with a pyrimidine ring are formed in the reaction of vicinal azido carboxylic acids 136 or their esters (X = COOR, where R = H, Alk) with derivatives of acetonitrile. 1,2,3-Triazolo[1,5-a]quinazo-lines 139 [79] and 140 [80,81] and also triazoles 141-143, condensed with pyrrolopyrimidine [82,83] and indolopyrimidine rings [84], were synthesized in this way. Triazolo[1,5-a]quinazolines of type 144 are formed during the reaction of 2-azidoacetophenones 136 (X = COR, where R = Alk) with arylacetonitriles in aprotic solvents [85].…”