Literature DB >> 20401403

Highly efficient synthesis and characterization of the GPR30-selective agonist G-1 and related tetrahydroquinoline analogs.

Ritwik Burai1, Chinnasamy Ramesh, Marvin Shorty, Ramona Curpan, Cristian Bologa, Larry A Sklar, Tudor Oprea, Eric R Prossnitz, Jeffrey B Arterburn.   

Abstract

The GPR30 agonist probe G-1 and structural analogs were efficiently synthesized using multicomponent or stepwise Sc(III)-catalyzed aza-Diels-Alder cyclization. Optimization of solvent and reaction temperature provided enhanced endo-diastereoselectivity.

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Year:  2010        PMID： 20401403      PMCID： PMC2913306          DOI： 10.1039/c001307b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  34 in total

1.  Nuclear and extranuclear pathway inputs in the regulation of global gene expression by estrogen receptors.

Authors:  Zeynep Madak-Erdogan; Karen J Kieser; Sung Hoon Kim; Barry Komm; John A Katzenellenbogen; Benita S Katzenellenbogen
Journal:  Mol Endocrinol       Date:  2008-07-10

2.  First asymmetric synthesis of quinoline derivatives by inverse electron demand (IED) Diels-Alder reaction using chiral Ti(IV) complex.

Authors:  G Sundararajan; N Prabagaran; B Varghese
Journal:  Org Lett       Date:  2001-06-28       Impact factor: 6.005

3.  Nonradical zinc-Barbier reaction for diastereoselective synthesis of vicinal amino alcohols.

Authors:  Lise Keinicke; Peter Fristrup; Per-Ola Norrby; Robert Madsen
Journal:  J Am Chem Soc       Date:  2005-11-16       Impact factor: 15.419

4.  Regulatory role of G protein-coupled estrogen receptor for vascular function and obesity.

Authors:  Elvira Haas; Indranil Bhattacharya; Eugen Brailoiu; Marlen Damjanović; G Cristina Brailoiu; Xin Gao; Laurence Mueller-Guerre; Nicole A Marjon; André Gut; Roberta Minotti; Matthias R Meyer; Kerstin Amann; Emerita Ammann; Ana Perez-Dominguez; Michele Genoni; Deborah J Clegg; Nae J Dun; Thomas C Resta; Eric R Prossnitz; Matthias Barton
Journal:  Circ Res       Date:  2009-01-29       Impact factor: 17.367

Review 5.  Association of the membrane estrogen receptor, GPR30, with breast tumor metastasis and transactivation of the epidermal growth factor receptor.

Authors:  Edward J Filardo; Jeffrey A Quinn; Edmond Sabo
Journal:  Steroids       Date:  2008-01-03       Impact factor: 2.668

6.  In vivo effects of a GPR30 antagonist.

Authors:  Megan K Dennis; Ritwik Burai; Chinnasamy Ramesh; Whitney K Petrie; Sara N Alcon; Tapan K Nayak; Cristian G Bologa; Andrei Leitao; Eugen Brailoiu; Elena Deliu; Nae J Dun; Larry A Sklar; Helen J Hathaway; Jeffrey B Arterburn; Tudor I Oprea; Eric R Prossnitz
Journal:  Nat Chem Biol       Date:  2009-06       Impact factor: 15.040

7.  Nonclassical estrogen modulation of presynaptic GABA terminals modulates calcium dynamics in gonadotropin-releasing hormone neurons.

Authors:  Nicola Romanò; Kiho Lee; István M Abrahám; Christine L Jasoni; Allan E Herbison
Journal:  Endocrinology       Date:  2008-08-14       Impact factor: 4.736

8.  A crowdsourcing evaluation of the NIH chemical probes.

Authors:  Tudor I Oprea; Cristian G Bologa; Scott Boyer; Ramona F Curpan; Robert C Glen; Andrew L Hopkins; Christopher A Lipinski; Garland R Marshall; Yvonne C Martin; Liliana Ostopovici-Halip; Gilbert Rishton; Oleg Ursu; Roy J Vaz; Chris Waller; Herbert Waldmann; Larry A Sklar
Journal:  Nat Chem Biol       Date:  2009-07       Impact factor: 15.040

9.  Involvement of G protein-coupled receptor 30 (GPR30) in rapid action of estrogen in primate LHRH neurons.

Authors:  Sekoni D Noel; Kim L Keen; David I Baumann; Edward J Filardo; Ei Terasawa
Journal:  Mol Endocrinol       Date:  2009-01-08

10.  The G protein-coupled receptor GPR30 inhibits human urothelial cell proliferation.

Authors:  Jian Teng; Zun-Yi Wang; Eric R Prossnitz; Dale E Bjorling
Journal:  Endocrinology       Date:  2008-05-08       Impact factor: 4.736
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  14 in total

1.  Role of GPER in estrogen-dependent nitric oxide formation and vasodilation.

Authors:  Natalie C Fredette; Matthias R Meyer; Eric R Prossnitz
Journal:  J Steroid Biochem Mol Biol       Date:  2017-05-18       Impact factor: 4.292

2.  A Selective Ligand for Estrogen Receptor Proteins Discriminates Rapid and Genomic Signaling.

Authors:  Chetana M Revankar; Cristian G Bologa; Richard A Pepermans; Geetanjali Sharma; Whitney K Petrie; Sara N Alcon; Angela S Field; Chinnasamy Ramesh; Matthew A Parker; Nikolay P Savchuk; Larry A Sklar; Helen J Hathaway; Jeffrey B Arterburn; Tudor I Oprea; Eric R Prossnitz
Journal:  Cell Chem Biol       Date:  2019-11-06       Impact factor: 8.116

Review 3.  International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators.

Authors:  Eric R Prossnitz; Jeffrey B Arterburn
Journal:  Pharmacol Rev       Date:  2015-07       Impact factor: 25.468

4.  Identification of a GPER/GPR30 antagonist with improved estrogen receptor counterselectivity.

Authors:  Megan K Dennis; Angela S Field; Ritwik Burai; Chinnasamy Ramesh; Whitney K Petrie; Cristian G Bologa; Tudor I Oprea; Yuri Yamaguchi; Shin-Ichi Hayashi; Larry A Sklar; Helen J Hathaway; Jeffrey B Arterburn; Eric R Prossnitz
Journal:  J Steroid Biochem Mol Biol       Date:  2011-07-14       Impact factor: 4.292

Review 5.  Contributions of academic laboratories to the discovery and development of chemical biology tools.

Authors:  Donna M Huryn; Lynn O Resnick; Peter Wipf
Journal:  J Med Chem       Date:  2013-05-31       Impact factor: 7.446

6.  Microwave-assisted Expeditious and Efficient Synthesis of Cyclopentene Ring-fused Tetrahydroquinoline Derivatives Using Three-component Povarov Reaction.

Authors:  Abhijit R Kulkarni; Ganesh A Thakur
Journal:  Tetrahedron Lett       Date:  2013-11-27       Impact factor: 2.415

7.  G protein-coupled estrogen receptor inhibits vascular prostanoid production and activity.

Authors:  Matthias R Meyer; Natalie C Fredette; Matthias Barton; Eric R Prossnitz
Journal:  J Endocrinol       Date:  2015-08-24       Impact factor: 4.286

8.  Preclinical efficacy of the GPER-selective agonist G-1 in mouse models of obesity and diabetes.

Authors:  Geetanjali Sharma; Chelin Hu; Daniela I Staquicini; Jonathan L Brigman; Meilian Liu; Franck Mauvais-Jarvis; Renata Pasqualini; Wadih Arap; Jeffrey B Arterburn; Helen J Hathaway; Eric R Prossnitz
Journal:  Sci Transl Med       Date:  2020-01-29       Impact factor: 17.956

9.  G protein-coupled estrogen receptor protects from atherosclerosis.

Authors:  Matthias R Meyer; Natalie C Fredette; Tamara A Howard; Chelin Hu; Chinnasamy Ramesh; Christoph Daniel; Kerstin Amann; Jeffrey B Arterburn; Matthias Barton; Eric R Prossnitz
Journal:  Sci Rep       Date:  2014-12-23       Impact factor: 4.379

10.  Synthesis and characterization of tricarbonyl-Re/Tc(I) chelate probes targeting the G protein-coupled estrogen receptor GPER/GPR30.

Authors:  Ritwik Burai; Chinnasamy Ramesh; Tapan K Nayak; Megan K Dennis; Bj K Bryant; Eric R Prossnitz; Jeffrey B Arterburn
Journal:  PLoS One       Date:  2012-10-15       Impact factor: 3.240
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