Literature DB >> 20161231

Microwave-Assisted Direct Biaryl Coupling: First Application to the Synthesis of Aporphines.

Sandeep Chaudhary1, Stevan Pecic, Onica Legendre, Wayne W Harding.   

Abstract

We have investigated the use of microwaves in a direct biaryl coupling reaction for the synthesis of analogs of the aporphine alkaloid nantenine. Our study shows that the aporphine core may be rapidly accessed from benzyl-tetrahydroisoquinoline substrates with this method. This is the first report of a microwave-assisted direct biaryl coupling reaction in the synthesis of aporphine molecules.

Entities:  

Year:  2009        PMID： 20161231      PMCID： PMC2704556          DOI： 10.1016/j.tetlet.2009.03.029

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  27 in total

1.  Ligand-free palladium catalysis of the Suzuki reaction in water using microwave heating.

Authors:  Nicholas E Leadbeater; Maria Marco
Journal:  Org Lett       Date:  2002-08-22       Impact factor: 6.005

2.  Microwave-promoted Heck coupling using ultralow metal catalyst concentrations.

Authors:  Riina K Arvela; Nicholas E Leadbeater
Journal:  J Org Chem       Date:  2005-03-04       Impact factor: 4.354

3.  The Heck-Mizoroki cross-coupling reaction: a mechanistic perspective.

Authors:  Jonathan P Knowles; Andrew Whiting
Journal:  Org Biomol Chem       Date:  2006-11-09       Impact factor: 3.876

4.  Direct intramolecular arylation of unactivated arenes: application to the synthesis of aporphine alkaloids.

Authors:  Marc Lafrance; Nicole Blaquière; Keith Fagnou
Journal:  Chem Commun (Camb)       Date:  2004-10-25       Impact factor: 6.222

5.  Pharmacological effects of (+)-nantenine, an alkaloid isolated from Platycapnos spicata, in several rat isolated tissues.

Authors:  Francisco Orallo
Journal:  Planta Med       Date:  2003-02       Impact factor: 3.352

6.  Aporphine synthesis by Pschorr cyclization of aminophenols. An improved synthesis of a thalicarpine precursor.

Authors:  S M Kupchan; V Kameswaran; J W Findlay
Journal:  J Org Chem       Date:  1973-01-26       Impact factor: 4.354

Review 7.  Cytotoxic and antitumor potentialities of aporphinoid alkaloids.

Authors:  C Stévigny; C Bailly; J Quetin-Leclercq
Journal:  Curr Med Chem Anticancer Agents       Date:  2005-03

8.  Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity.

Authors:  Bachtiar Indra; Kimihiro Matsunaga; Osamu Hoshino; Masaji Suzuki; Hiromichi Ogasawara; Yasushi Ohizumi
Journal:  Eur J Pharmacol       Date:  2002-02-22       Impact factor: 4.432

9.  Efficient palladium(II) catalysis under air. Base-free oxidative heck reactions at room temperature or with microwave heating.

Authors:  Jonas Lindh; Per-Anders Enquist; Ake Pilotti; Peter Nilsson; Mats Larhed
Journal:  J Org Chem       Date:  2007-09-21       Impact factor: 4.354

10.  Rh(I)-catalyzed arylation of heterocycles via C-H bond activation: expanded scope through mechanistic insight.

Authors:  Jared C Lewis; Ashley M Berman; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2008-02-02       Impact factor: 15.419
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  13 in total

1.  Nantenine as an acetylcholinesterase inhibitor: SAR, enzyme kinetics and molecular modeling investigations.

Authors:  Stevan Pecic; Marie A McAnuff; Wayne W Harding
Journal:  J Enzyme Inhib Med Chem       Date:  2010-06-28       Impact factor: 5.051

2.  Cytotoxicity of aporphines in human colon cancer cell lines HCT-116 and Caco-2: an SAR study.

Authors:  Shashikanth Ponnala; Sandeep Chaudhary; Antonio González-Sarrias; Navindra P Seeram; Wayne W Harding
Journal:  Bioorg Med Chem Lett       Date:  2011-06-15       Impact factor: 2.823

3.  Evaluation of structural effects on 5-HT(2A) receptor antagonism by aporphines: identification of a new aporphine with 5-HT(2A) antagonist activity.

Authors:  Shashikanth Ponnala; Junior Gonzales; Nirav Kapadia; Hernan A Navarro; Wayne W Harding
Journal:  Bioorg Med Chem Lett       Date:  2014-03-04       Impact factor: 2.823

4.  Synthesis and evaluation of aporphine analogs containing C1 allyl isosteres at the h5-HT(2A) receptor.

Authors:  Shashikanth Ponnala; Nirav Kapadia; Sudharshan Madapa; Ian L Alberts; Wayne W Harding
Journal:  Bioorg Med Chem Lett       Date:  2015-10-09       Impact factor: 2.823

5.  Identification of C10 nitrogen-containing aporphines with dopamine D1 versus D5 receptor selectivity.

Authors:  Anupam Karki; Reecan Juarez; Hari K Namballa; Ian Alberts; Wayne W Harding
Journal:  Bioorg Med Chem Lett       Date:  2020-02-20       Impact factor: 2.823

6.  Synthesis, pharmacological evaluations, and molecular docking studies on a new 1,3,4,11b-tetrahydro-1H-fluoreno[9,1-cd]azepine framework: Rigidification of D1 receptor selective 1-phenylbenzazepines and discovery of a new 5-HT6 receptor scaffold.

Authors:  Rajan Giri; Ian Alberts; Wayne W Harding
Journal:  Chem Biol Drug Des       Date:  2020-04-22       Impact factor: 2.817

7.  New aporphinoid 5-HT2A and α1A antagonists via structural manipulations of nantenine.

Authors:  Sandeep Chaudhary; Shashikanth Ponnala; Onica Legendre; Junior A Gonzales; Hernán A Navarro; Wayne W Harding
Journal:  Bioorg Med Chem       Date:  2011-08-18       Impact factor: 3.641

8.  Synthetic studies and pharmacological evaluations on the MDMA ('Ecstasy') antagonist nantenine.

Authors:  Onica Legendre; Stevan Pecic; Sandeep Chaudhary; Sarah M Zimmerman; William E Fantegrossi; Wayne W Harding
Journal:  Bioorg Med Chem Lett       Date:  2009-11-20       Impact factor: 2.823

9.  A New Route to Azafluoranthene Natural Products via Direct Arylation.

Authors:  Shashikanth Ponnala; Wayne W Harding
Journal:  European J Org Chem       Date:  2013-01-03

10.  Facile synthesis of 4,5,6a,7-tetrahydrodibenzo[de,g]chromene heterocycles and their transformation to phenanthrene alkaloids.

Authors:  Nirav Kapadia; Wayne Harding
Journal:  Tetrahedron       Date:  2013-10-21       Impact factor: 2.457
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