Literature DB >> 15951062

Regioselective synthesis and estrogenicity of (+/-)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins.

Frederik Roelens1, Kevin Huvaere, Willem Dhooge, Marjan Van Cleemput, Frank Comhaire, Denis De Keukeleire.   

Abstract

Nine new (+/-)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins have been synthesized from 2,4,6-trimethoxybenzaldehyde via a short, efficient, and regioselective pathway, together with the unsubstituted analogue (+/-)-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarin. The compounds were tested for estrogenic activity using a yeast-based estrogen screen. Weak estrogenicity was determined for seven members of the series.

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Year:  2005        PMID: 15951062     DOI: 10.1016/j.ejmech.2005.04.010

Source DB:  PubMed          Journal:  Eur J Med Chem        ISSN: 0223-5234            Impact factor:   6.514


  5 in total

Review 1.  Recent progress of isocyanide-based multicomponent reactions in Iran.

Authors:  Ahmad Shaabani; Ali Maleki; Ali Hossein Rezayan; Afshin Sarvary
Journal:  Mol Divers       Date:  2010-07-29       Impact factor: 2.943

2.  Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization.

Authors:  John A Malona; Kevin Cariou; William T Spencer; Alison J Frontier
Journal:  J Org Chem       Date:  2012-01-26       Impact factor: 4.354

3.  N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Chem Commun (Camb)       Date:  2015-02-25       Impact factor: 6.222

4.  rac-(1S,2R)-Diethyl 6-hydr-oxy-1-(4-methoxy-phen-yl)-3-oxo-2,3-di-hydro-1H-benzo[f]chromen-2-yl]-phospho-nate.

Authors:  Jakub Wojciechowski; Henryk Krawczyk; Lukasz Albrecht; Wojciech M Wolf
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-06-07

5.  A novel method for the synthesis of substituted 3,4-dihydrocoumarin derivatives via isocyanide-based three-component reaction.

Authors:  Ahmad Shaabani; Afshin Sarvary; Ebrahim Soleimani; Ali Hossein Rezayan; Marjan Heidary
Journal:  Mol Divers       Date:  2008-10-01       Impact factor: 2.943

  5 in total

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