Several 3-carbonyl (1e26), 3-acyl (27e52), and 3-carboxyhydrazido (53e58) coumarins have been synthesized in high yields (72e99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl ester coumarin ring, or the introduction of a hydrazido substituent at C3, were important to obtain highly potent and selective hMAO-B inhibitors with IC50 values in the nanomolar range. Some derivatives were also submitted to a stability test and showed no chemical cleavage in vitro.

Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives / Secci, Daniela; Carradori, Simone; Bolasco, Adriana; Chimenti, Paola; Yanez, Matilde; Ortuso, Francesco; Alcaro, Stefano. - In: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0223-5234. - STAMPA. - 46:(2011), pp. 4846-4852. [10.1016/j.ejmech.2011.07.017]

Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives

SECCI, DANIELA;CARRADORI, Simone;BOLASCO, Adriana;CHIMENTI, Paola;
2011

Abstract

Several 3-carbonyl (1e26), 3-acyl (27e52), and 3-carboxyhydrazido (53e58) coumarins have been synthesized in high yields (72e99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl ester coumarin ring, or the introduction of a hydrazido substituent at C3, were important to obtain highly potent and selective hMAO-B inhibitors with IC50 values in the nanomolar range. Some derivatives were also submitted to a stability test and showed no chemical cleavage in vitro.
2011
Monoamine oxidase, Coumarin, Hydrazido, Hydrolytic stability
01 Pubblicazione su rivista::01a Articolo in rivista
Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives / Secci, Daniela; Carradori, Simone; Bolasco, Adriana; Chimenti, Paola; Yanez, Matilde; Ortuso, Francesco; Alcaro, Stefano. - In: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0223-5234. - STAMPA. - 46:(2011), pp. 4846-4852. [10.1016/j.ejmech.2011.07.017]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/543282
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