Literature DB >> 14761209

Importance of phenolic address groups in opioid kappa receptor selective antagonists.

James B Thomas1, Scott E Fix, Richard B Rothman, S Wayne Mascarella, Christina M Dersch, Buddy E Cantrell, Dennis M Zimmerman, F Ivy Carroll.   

Abstract

In vitro characterization and comparison of JDTic, its dehydroxy analogue and nor-BNI, and its dehydroxy analogue demonstrates that the N-substituted 3,4-dimethyl-(3-hydroxyphenyl)piperidine-derived antagonist, JDTic, relies more heavily on its phenol address group for affinity and antagonist activity relative to the corresponding naltrexone derived antagonists, nor-BNI. The structural flexibility of the former class of compound relative to the latter is postulated to underlie the difference.

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Year:  2004        PMID： 14761209     DOI： 10.1021/jm030467v

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  12 in total

1.  Effectiveness of analogs of the kappa opioid receptor antagonist (3R)-7-hydroxy-N-((1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic) to reduce U50,488-induced diuresis and stress-induced cocaine reinstatement in rats.

Authors:  Patrick M Beardsley; Gerald T Pollard; James L Howard; F Ivy Carroll
Journal:  Psychopharmacology (Berl)       Date:  2010-04-07       Impact factor: 4.530

2.  Duration of action of a broad range of selective κ-opioid receptor antagonists is positively correlated with c-Jun N-terminal kinase-1 activation.

Authors:  Erica J Melief; Mayumi Miyatake; F Ivy Carroll; Cécile Béguin; William A Carlezon; Bruce M Cohen; Sarah Grimwood; Charles H Mitch; Linda Rorick-Kehn; Charles Chavkin
Journal:  Mol Pharmacol       Date:  2011-08-10       Impact factor: 4.436

Review 3.  Kappa opioid antagonists: past successes and future prospects.

Authors:  Matthew D Metcalf; Andrew Coop
Journal:  AAPS J       Date:  2005-10-27       Impact factor: 4.009

Review 4.  The discovery and development of the N-substituted trans-3,4-dimethyl-4-(3'-hydroxyphenyl)piperidine class of pure opioid receptor antagonists.

Authors:  F Ivy Carroll; Roland E Dolle
Journal:  ChemMedChem       Date:  2014-06-30       Impact factor: 3.466

5.  Differential effects of the novel kappa opioid receptor antagonist, JDTic, on reinstatement of cocaine-seeking induced by footshock stressors vs cocaine primes and its antidepressant-like effects in rats.

Authors:  Patrick M Beardsley; James L Howard; Keith L Shelton; F Ivy Carroll
Journal:  Psychopharmacology (Berl)       Date:  2005-10-22       Impact factor: 4.530

6.  Characterization of BU09059: a novel potent selective κ-receptor antagonist.

Authors:  Joseph J Casal-Dominguez; Daniel Furkert; Mehrnoosh Ostovar; Linnea Teintang; Mary J Clark; John R Traynor; Stephen M Husbands; Sarah J Bailey
Journal:  ACS Chem Neurosci       Date:  2014-01-28       Impact factor: 4.418

Review 7.  Role of kappa-opioid receptors in stress and anxiety-related behavior.

Authors:  Ashlee Van't Veer; William A Carlezon
Journal:  Psychopharmacology (Berl)       Date:  2013-07-09       Impact factor: 4.530

8.  Analogues of (3R)-7-hydroxy-N-[(1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic). Synthesis and in vitro and in vivo opioid receptor antagonist activity.

Authors:  Scott P Runyon; Lawrence E Brieaddy; S Wayne Mascarella; James B Thomas; Hernán A Navarro; James L Howard; Gerald T Pollard; F Ivy Carroll
Journal:  J Med Chem       Date:  2010-07-22       Impact factor: 7.446

9.  Long-acting kappa opioid antagonists disrupt receptor signaling and produce noncompetitive effects by activating c-Jun N-terminal kinase.

Authors:  Michael R Bruchas; Tao Yang; Selena Schreiber; Mia Defino; Steven C Kwan; Shuang Li; Charles Chavkin
Journal:  J Biol Chem       Date:  2007-08-16       Impact factor: 5.157

10.  Structure of the human κ-opioid receptor in complex with JDTic.

Authors:  Huixian Wu; Daniel Wacker; Mauro Mileni; Vsevolod Katritch; Gye Won Han; Eyal Vardy; Wei Liu; Aaron A Thompson; Xi-Ping Huang; F Ivy Carroll; S Wayne Mascarella; Richard B Westkaemper; Philip D Mosier; Bryan L Roth; Vadim Cherezov; Raymond C Stevens
Journal:  Nature       Date:  2012-03-21       Impact factor: 49.962
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