Synthesis and Biological Evaluation of New Quinazoline and Cinnoline Derivatives as Potential Atypical Antipsychotics
2006; Wiley; Volume: 3; Issue: 1 Linguagem: Inglês
10.1002/cbdv.200690001
ISSN1612-1880
AutoresMario Alvarado, María Barceló, L. Carro, Christian F. Masaguer, Enrique Raviña,
Tópico(s)Synthesis and Reactivity of Heterocycles
ResumoChemistry & BiodiversityVolume 3, Issue 1 p. 106-117 Research Article Synthesis and Biological Evaluation of New Quinazoline and Cinnoline Derivatives as Potential Atypical Antipsychotics† Mario Alvarado, Mario Alvarado Departamento de Química Orgánica, Laboratorio de Química Farmacéutica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15782, Santiago de Compostela, SpainSearch for more papers by this authorMaría Barceló, María Barceló Departamento de Química Orgánica, Laboratorio de Química Farmacéutica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15782, Santiago de Compostela, SpainSearch for more papers by this authorLaura Carro, Laura Carro Departamento de Química Orgánica, Laboratorio de Química Farmacéutica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15782, Santiago de Compostela, SpainSearch for more papers by this authorChristian F. Masaguer, Christian F. Masaguer Departamento de Química Orgánica, Laboratorio de Química Farmacéutica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15782, Santiago de Compostela, SpainSearch for more papers by this authorEnrique Raviña, Enrique Raviña qofara@usc.es Departamento de Química Orgánica, Laboratorio de Química Farmacéutica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15782, Santiago de Compostela, SpainSearch for more papers by this author Mario Alvarado, Mario Alvarado Departamento de Química Orgánica, Laboratorio de Química Farmacéutica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15782, Santiago de Compostela, SpainSearch for more papers by this authorMaría Barceló, María Barceló Departamento de Química Orgánica, Laboratorio de Química Farmacéutica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15782, Santiago de Compostela, SpainSearch for more papers by this authorLaura Carro, Laura Carro Departamento de Química Orgánica, Laboratorio de Química Farmacéutica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15782, Santiago de Compostela, SpainSearch for more papers by this authorChristian F. Masaguer, Christian F. Masaguer Departamento de Química Orgánica, Laboratorio de Química Farmacéutica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15782, Santiago de Compostela, SpainSearch for more papers by this authorEnrique Raviña, Enrique Raviña qofara@usc.es Departamento de Química Orgánica, Laboratorio de Química Farmacéutica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15782, Santiago de Compostela, SpainSearch for more papers by this author First published: 19 January 2006 https://doi.org/10.1002/cbdv.200690001Citations: 45 † This is the 33rd paper in the series 'Synthesis and CNS Activity of Conformationally Restricted Butyrophenones'. For the preceding paper, see [1]. AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract Four new diaza analogues (14, 15, 23, and 24) of the conformationally constrained aminobutyrophenone derivatives QF0104B (5) and QF0108B (6) were synthesized (Schemes 2 and 3), and evaluated for their binding affinities (Table) towards the serotonin 5-HT2A and 5-HT2C, and the dopamine D2 receptors. Among the new compounds, the quinazoline derivative 15 (=7-{[4-(4-fluorobenzoyl)piperidin-1-yl]methyl}-5,6,7,8-tetrahydroquinazolin-5-one) exhibited the highest affinities towards the serotonin 5-HT2A and dopamine D2 receptors, and it is in the borderline of potential atypical antipsychotics. The cinnoline derivative 23 (=7-{[4-(4-fluorobenzoyl)piperidin-1-yl]methyl}-5,6,7,8-tetrahydro-3-methylcinnolin-5-one) displayed high selectivity in its binding profile towards the 5-HT2C compared to both the 5-HT2A and D2 receptors. Citing Literature Volume3, Issue1January 2006Pages 106-117 RelatedInformation
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