139193-06-9Relevant academic research and scientific papers
Radical reactions with 3H-quinazolin-4-ones: Synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin
Bowman, W. Russell,Elsegood, Mark R. J.,Stein, Tobias,Weaver, George W.
, p. 103 - 113 (2008/03/14)
Alkyl, aryl, heteroaryl and acyl radicals have been cyclised onto the 2-position of 3H-quinazolin-4-one. The side chains containing the radical precursors were attached to the nitrogen atom in the 3-position. The cyclisations take place by aromatic homolytic substitution hence retain the aromaticity of the 3H-quinazolin-4-one ring. The highest yields were obtained using hexamethylditin to facilitate cyclisation rather than reduction without cyclisation. The alkaloids deoxyvasicinone 2, mackinazolinone 3, tryptanthrin 4, luotonin A 5 and rutaecarpine 8 were synthesised by radical cyclisation onto 3H-quinazolin-4-one. This journal is The Royal Society of Chemistry.
Synthesis and pharmacological evaluation of new arylpiperazines. 3-{4-[4-(3-chlorophenyl)-1-piperazinyl]butyl}-quinazolidin-4-one - A dual serotonin 5-HT1A/5-HT2A receptor ligand with an anxiolytic-like activity
Bojarski, Andrzej J.,Kowalski, Piotr,Kowalska, Teresa,Duszynska, Beata,Charakchieva-Minol, Sijka,Tatarczynska, Ewa,Klodzinska, Aleksandra,Chojnacka-Wojcik, Ewa
, p. 3817 - 3827 (2007/10/03)
On the basis of systematic studies on the structure-activity relationships in arylpiperazine group of serotonin ligands, 12 new derivatives containing quinazolidin-4(3H)-one (1-4), 2-phenyl-2,3-dihydrophthalazine-1,4-dione (5-8) or 1-phenyl-1,2-dihydropyridazine-3,6-dione (9-12) fragments were synthesized. The majority of the tested compounds (2, 4, 7, 8 and 10-12) showed a high affinity for 5-HT1A receptors (Ki=11-54 nM) and two (1, 2) were found active at 5-HT2A sites (16 and 68 nM, respectively). All the new 5-HT1A ligands tested in vivo revealed an antagonistic activity at postsynaptic 5-HT1A receptors, and three of them behaved as agonists at presynaptic ones. Additionally, both the meta-chlorophenylpiperazine derivatives containing quinazolidin-4-one fragment showed features of 5-HT2A receptor antagonists. The dual 5-HT1A/5-HT2A receptor ligand (2) was further tested for its potential psychotropic activity. It showed a distinct anxiolytic-like activity in a conflict drinking test in rats and the observed effect was more potent in terms of the active dose, than that produced by diazepam (used as a reference drug).
Biologically active 1-arylpiperazines. Synthesis of new N-(4-aryl-1-piperazinyl)alkyl derivatives of quinazolidin-4(3H)-one, 2,3-dihydrophthalazine-1,4-dione and 1,2-dihydropyridazine-3,6-dione as potential serotonin receptor ligands
Kowalski, Piotr,Kowalska, Teresa,Mokrosz, Maria J.,Bojarski, Andrzej J.,Charakchieva-Minol, Sijka
, p. 784 - 795 (2007/10/03)
The synthesis of a series of new n-propyl and n-butyl chain containing 1-arylpiperazine derivatives of quinazolidin-4(3H)-one (7) 2-phenyl-2,3- dihydrophthalazine-1,4-dione (8) and 1-phenyl-1,2-dihydropyridazine-3,6-dione (9) as potential serotonin receptor ligands is described.
