Literature DB >> 21875798

Towards rational design of cannabinoid receptor 1 (CB1) antagonists for peripheral selectivity.

Alan Fulp1, Katherine Bortoff, Yanan Zhang, Herbert Seltzman, Rodney Snyder, Rangan Maitra.   

Abstract

CB1 receptor antagonists that are peripherally restricted were targeted. Compounds with permanent charge as well as compounds that have increased polar surface area were made and tested against CB1 for binding and activity. Sulfonamide and sulfamide with high polar surface area and good activity at CB1 were rationally designed and pharmacologically tested. Further optimization of these compounds and testing could lead to the development of a new class of therapeutics to treat disorders where the CB1 receptor system has been implicated.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID： 21875798      PMCID： PMC3171605          DOI： 10.1016/j.bmcl.2011.08.032

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  20 in total

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Authors:  M Bouaboula; S Perrachon; L Milligan; X Canat; M Rinaldi-Carmona; M Portier; F Barth; B Calandra; F Pecceu; J Lupker; J P Maffrand; G Le Fur; P Casellas
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3.  Peripheral CB1 cannabinoid receptor blockade improves cardiometabolic risk in mouse models of obesity.

Authors:  Joseph Tam; V Kiran Vemuri; Jie Liu; Sándor Bátkai; Bani Mukhopadhyay; Grzegorz Godlewski; Douglas Osei-Hyiaman; Shinobu Ohnuma; Suresh V Ambudkar; James Pickel; Alexandros Makriyannis; George Kunos
Journal:  J Clin Invest       Date:  2010-07-26       Impact factor: 14.808

4.  Excellent correlation between substituent constants and pyridinium N-methyl chemical shifts.

Authors:  Sha Huang; Jesse C S Wong; Adam K C Leung; Yee Man Chan; Lili Wong; Myrien R Fernendez; Amanda K Miller; Weiming Wu
Journal:  Tetrahedron Lett       Date:  2009-09-02       Impact factor: 2.415

5.  Conversion of 4-cyanomethyl-pyrazole-3-carboxamides into CB1 antagonists with lowered propensity to pass the blood-brain-barrier.

Authors:  Jean-Marie Receveur; Anthony Murray; Jean-Michel Linget; Pia K Nørregaard; Martin Cooper; Emelie Bjurling; Peter Aadal Nielsen; Thomas Högberg
Journal:  Bioorg Med Chem Lett       Date:  2009-12-04       Impact factor: 2.823

6.  Pharmacological evaluation of LH-21, a newly discovered molecule that binds to cannabinoid CB1 receptor.

Authors:  Richard Z Chen; Andrea Frassetto; Julie Z Lao; Ruey-Ruey C Huang; Jing C Xiao; Matthew J Clements; Thomas F Walsh; Jeffrey J Hale; Junying Wang; Xinchun Tong; Tung M Fong
Journal:  Eur J Pharmacol       Date:  2008-02-19       Impact factor: 4.432

7.  A general modular method of azaindole and thienopyrrole synthesis via Pd-catalyzed tandem couplings of gem-dichloroolefins.

Authors:  Yuan-Qing Fang; Josephine Yuen; Mark Lautens
Journal:  J Org Chem       Date:  2007-06-09       Impact factor: 4.354

8.  Synthesis and characterization of a peripherally restricted CB1 cannabinoid antagonist, URB447, that reduces feeding and body-weight gain in mice.

Authors:  Jesse LoVerme; Andrea Duranti; Andrea Tontini; Gilberto Spadoni; Marco Mor; Silvia Rivara; Nephi Stella; Cong Xu; Giorgio Tarzia; Daniele Piomelli
Journal:  Bioorg Med Chem Lett       Date:  2008-12-24       Impact factor: 2.823

Review 9.  The current status and future perspectives of studies of cannabinoid receptor 1 antagonists as anti-obesity agents.

Authors:  Hyeon-Kyu Lee; Eun Bok Choi; Chwang Siek Pak
Journal:  Curr Top Med Chem       Date:  2009       Impact factor: 3.295

Review 10.  Cannabinoid receptor antagonists: pharmacological opportunities, clinical experience, and translational prognosis.

Authors:  David R Janero; Alexandros Makriyannis
Journal:  Expert Opin Emerg Drugs       Date:  2009-03       Impact factor: 4.191
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  13 in total

1.  Design of a Potent CB1 Receptor Antagonist Series: Potential Scaffold for Peripherally-Targeted Agents.

Authors:  Robert L Dow; Philip A Carpino; Denise Gautreau; John R Hadcock; Philip A Iredale; Dawn Kelly-Sullivan; Jeffrey S Lizano; Rebecca E O'Connor; Steven R Schneider; Dennis O Scott; Karen M Ward
Journal:  ACS Med Chem Lett       Date:  2012-03-21       Impact factor: 4.345

2.  Peripherally Selective Cannabinoid 1 Receptor (CB1R) Agonists for the Treatment of Neuropathic Pain.

Authors:  Herbert H Seltzman; Craig Shiner; Erin E Hirt; Anne F Gilliam; Brian F Thomas; Rangan Maitra; Rod Snyder; Sherry L Black; Purvi R Patel; Yatendra Mulpuri; Igor Spigelman
Journal:  J Med Chem       Date:  2016-08-10       Impact factor: 7.446

3.  Functionalized 6-(Piperidin-1-yl)-8,9-Diphenyl Purines as Peripherally Restricted Inverse Agonists of the CB1 Receptor.

Authors:  George Amato; Amruta Manke; Robert Wiethe; Vineetha Vasukuttan; Rodney Snyder; Yun Lan Yueh; Ann Decker; Scott Runyon; Rangan Maitra
Journal:  J Med Chem       Date:  2019-06-22       Impact factor: 7.446

4.  Structural analogs of pyrazole and sulfonamide cannabinoids: effects on acute food intake in mice.

Authors:  Jenny L Wiley; Julie A Marusich; Yanan Zhang; Alan Fulp; Rangan Maitra; Brian F Thomas; Anu Mahadevan
Journal:  Eur J Pharmacol       Date:  2012-09-06       Impact factor: 4.432

5.  Functionalized 6-(piperidin-1-yl)-8,9-diphenyl purines as inverse agonists of the CB1 receptor - SAR efforts towards selectivity and peripheralization.

Authors:  George Amato; Robert Wiethe; Amruta Manke; Vineetha Vasukuttan; Rodney Snyder; Scott Runyon; Rangan Maitra
Journal:  Bioorg Med Chem       Date:  2019-07-04       Impact factor: 3.641

6.  Diphenyl purine derivatives as peripherally selective cannabinoid receptor 1 antagonists.

Authors:  Alan Fulp; Katherine Bortoff; Yanan Zhang; Herbert Seltzman; James Mathews; Rodney Snyder; Tim Fennell; Rangan Maitra
Journal:  J Med Chem       Date:  2012-11-09       Impact factor: 7.446

7.  Synthesis and pharmacological characterization of functionalized 6-piperazin-1-yl-purines as cannabinoid receptor 1 (CB1) inverse agonists.

Authors:  George S Amato; Amruta Manke; Vineetha Vasukuttan; Robert W Wiethe; Rodney W Snyder; Scott P Runyon; Rangan Maitra
Journal:  Bioorg Med Chem       Date:  2018-07-27       Impact factor: 3.641

8.  Discovery of a Potent, Selective, and Brain-Penetrant Small Molecule that Activates the Orphan Receptor GPR88 and Reduces Alcohol Intake.

Authors:  Chunyang Jin; Ann M Decker; Viren H Makhijani; Joyce Besheer; Emmanuel Darcq; Brigitte L Kieffer; Rangan Maitra
Journal:  J Med Chem       Date:  2018-07-30       Impact factor: 7.446

9.  Design, synthesis, and pharmacological evaluation of JDTic analogs to examine the significance of the 3- and 4-methyl substituents.

Authors:  F Ivy Carroll; Moses G Gichinga; Chad M Kormos; Rangan Maitra; Scott P Runyon; James B Thomas; S Wayne Mascarella; Ann M Decker; Hernán A Navarro
Journal:  Bioorg Med Chem       Date:  2015-08-25       Impact factor: 3.641

10.  Pyrazole antagonists of the CB1 receptor with reduced brain penetration.

Authors:  Alan Fulp; Yanan Zhang; Katherine Bortoff; Herbert Seltzman; Rodney Snyder; Robert Wiethe; George Amato; Rangan Maitra
Journal:  Bioorg Med Chem       Date:  2016-01-18       Impact factor: 3.641
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