Convenient Synthesis of 1-Aryl-dihydroxyisochromans Exhibiting Antioxidant Activity

Roberta, Bernini; Crisante, Fernanda; Fabrizi, Giancarlo; Gentili, Patrizia

doi:10.2174/138527212800194700

Several 1-aryl-hydroxy and dihydroxyisochromans were synthesized by a two-steps procedure based on the oxa-Pictet-Spengler reaction performed for the first time in dimethyl carbonate (DMC) from phenethyl alcohols and substituted benzaldehydes followed by the regioselective aromatic hydroxylation/oxidative aromatic demethylation with 2-iodoxybenzoic acid (IBX)/sodium dithionite (Na2S2O4) system. Some of them showed a novel pattern of hydroxylation degree into A ring. All synthesized isochromans were tested about their radical scavenging activity by 2,2-diphenyl-2-picrylhydrazyl radical (DPPH center dot) method. Experimental results showed that dihydroxyisochromans were more active than the corresponding phenolic or guaiacolic parent compounds confirming the key role of the catecholic moiety for the antioxidant activity.

Convenient Synthesis of 1-Aryl-dihydroxyisochromans Exhibiting Antioxidant Activity / Roberta, Bernini; Crisante, Fernanda; Fabrizi, Giancarlo; Gentili, Patrizia. - In: CURRENT ORGANIC CHEMISTRY. - ISSN 1385-2728. - STAMPA. - 16:8(2012), pp. 1051-1057. [10.2174/138527212800194700]

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Titolo:	Convenient Synthesis of 1-Aryl-dihydroxyisochromans Exhibiting Antioxidant Activity
Autori:	Roberta Bernini CRISANTE, Fernanda FABRIZI, Giancarlo GENTILI, Patrizia mostra contributor esterni nascondi contributor esterni
Data di pubblicazione:	2012
Rivista:	CURRENT ORGANIC CHEMISTRY
Citazione:	Convenient Synthesis of 1-Aryl-dihydroxyisochromans Exhibiting Antioxidant Activity / Roberta, Bernini; Crisante, Fernanda; Fabrizi, Giancarlo; Gentili, Patrizia. - In: CURRENT ORGANIC CHEMISTRY. - ISSN 1385-2728. - STAMPA. - 16:8(2012), pp. 1051-1057. [10.2174/138527212800194700]
Handle:	http://hdl.handle.net/11573/448343
Appartiene alla tipologia:	01a Articolo in rivista

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