Literature DB >> 24474634

Synthesis of isoflavones by room-temperature nickel-catalyzed cross-couplings of 3-iodo(bromo)chromones with arylzincs.

Zunting Zhang1, Jinfeng Qiao, Ding Wang, Ling Han, Ru Ding.   

Abstract

A new concise, facile method for synthesis of isoflavones was accomplished in moderate to good yields for 3-iodochromones or 3-bromochromones and arylzinc bromides via Negishi cross-coupling reaction catalyzed by NiCl(2)/PPh(3) or NiCl(2)(PPh(3))(2) at room temperature. The Isoflavone core was synthesized in four steps in good yield, starting from commercially available 2-hydroxyacetophenone and aromatic bromide. Three steps of the procedure were carried out at room temperature.

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Year:  2014        PMID: 24474634     DOI: 10.1007/s11030-013-9495-1

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  11 in total

Review 1.  Stereoselective synthesis of monomeric flavonoids.

Authors:  Jannie P J Marais; Daneel Ferreira; Desmond Slade
Journal:  Phytochemistry       Date:  2005-09       Impact factor: 4.072

2.  Structural studies on bioactive compounds. 40.(1) Synthesis and biological properties of fluoro-, methoxyl-, and amino-substituted 3-phenyl-4H-1-benzopyran-4-ones and a comparison of their antitumor activities with the activities of related 2-phenylbenzothiazoles.

Authors:  David A Vasselin; Andrew D Westwell; Charles S Matthews; Tracey D Bradshaw; Malcolm F G Stevens
Journal:  J Med Chem       Date:  2006-06-29       Impact factor: 7.446

Review 3.  Dietary agents in cancer prevention: flavonoids and isoflavonoids.

Authors:  D F Birt; S Hendrich; W Wang
Journal:  Pharmacol Ther       Date:  2001 May-Jun       Impact factor: 12.310

Review 4.  The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer.

Authors:  E Middleton; C Kandaswami; T C Theoharides
Journal:  Pharmacol Rev       Date:  2000-12       Impact factor: 25.468

5.  Antiviral isoflavonoid sulfate and steroidal glycosides from the fruits of Solanum torvum.

Authors:  Damrongkiet Arthan; Jisnuson Svasti; Prasat Kittakoop; Daraporn Pittayakhachonwut; Morakot Tanticharoen; Yodhathai Thebtaranonth
Journal:  Phytochemistry       Date:  2002-02       Impact factor: 4.072

6.  Antiproliferative activity of various flavonoids and related compounds: additive effect of interferon-alpha2b.

Authors:  Viviana C Blank; Cecilia Poli; Mariel Marder; Leonor P Roguin
Journal:  Bioorg Med Chem Lett       Date:  2004-01-05       Impact factor: 2.823

7.  Anti-inflammatory isoflavonoids from the stems of Derris scandens.

Authors:  Pisamai Laupattarakasem; Peter J Houghton; J Robin S Hoult
Journal:  Planta Med       Date:  2004-06       Impact factor: 3.352

8.  Lewis acid-triggered selective zincation of chromones, quinolones, and thiochromones: application to the preparation of natural flavones and isoflavones.

Authors:  Lydia Klier; Tomke Bresser; Tobias A Nigst; Konstantin Karaghiosoff; Paul Knochel
Journal:  J Am Chem Soc       Date:  2012-08-09       Impact factor: 15.419

9.  Understanding the cardioprotective effects of flavonols: discovery of relaxant flavonols without antioxidant activity.

Authors:  Cheng Xue Qin; Xingqiang Chen; Richard A Hughes; Spencer J Williams; Owen L Woodman
Journal:  J Med Chem       Date:  2008-02-29       Impact factor: 7.446

10.  Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.

Authors:  Xing-Cong Li; Alpana S Joshi; Hala N ElSohly; Shabana I Khan; Melissa R Jacob; Zhizheng Zhang; Ikhlas A Khan; Daneel Ferreira; Larry A Walker; Sheldon E Broedel; Robert E Raulli; Ronald L Cihlar
Journal:  J Nat Prod       Date:  2002-12       Impact factor: 4.050

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