Literature DB >> 19097888

Synthesis and CB1 cannabinoid receptor affinity of 4-alkoxycarbonyl-1,5-diaryl-1,2,3-triazoles.

Hong Shu1, Sari Izenwasser, Dean Wade, Edwin D Stevens, Mark L Trudell.   

Abstract

A series of 4-alkoxycarbonyl-1,5-diaryl-1,2,3-triazoles were synthesized regioselectively using click chemistry and evaluated at CB1 cannabinoid receptors. The n-propyl ester 11 (K(i)=4.6 nM) and phenyl ester 14 (K(i)=11 nM) exhibited the most potent affinity of the series.

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Year:  2008        PMID: 19097888      PMCID: PMC2631625          DOI: 10.1016/j.bmcl.2008.11.110

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


  31 in total

Review 1.  Drug-like properties and the causes of poor solubility and poor permeability.

Authors:  C A Lipinski
Journal:  J Pharmacol Toxicol Methods       Date:  2000 Jul-Aug       Impact factor: 1.950

2.  Cannabinoid ligands and their effects on learning and performance in rhesus monkeys.

Authors:  P J Winsauer; P Lambert; J M Moerschbaecher
Journal:  Behav Pharmacol       Date:  1999-09       Impact factor: 2.293

3.  Molecular interaction of the antagonist N-(piperidin-1-yl)-5-(4-chlorophenyl)-1- (2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide with the CB1 cannabinoid receptor.

Authors:  Joong-Youn Shim; William J Welsh; Etienne Cartier; James L Edwards; Allyn C Howlett
Journal:  J Med Chem       Date:  2002-03-28       Impact factor: 7.446

Review 4.  International Union of Pharmacology. XXVII. Classification of cannabinoid receptors.

Authors:  A C Howlett; F Barth; T I Bonner; G Cabral; P Casellas; W A Devane; C C Felder; M Herkenham; K Mackie; B R Martin; R Mechoulam; R G Pertwee
Journal:  Pharmacol Rev       Date:  2002-06       Impact factor: 25.468

5.  N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716A) interaction with LYS 3.28(192) is crucial for its inverse agonism at the cannabinoid CB1 receptor.

Authors:  Dow P Hurst; Diane L Lynch; Judy Barnett-Norris; Stephen M Hyatt; Herbert H Seltzman; Miao Zhong; Zhao-Hui Song; Jingjiang Nie; Deborah Lewis; Patricia H Reggio
Journal:  Mol Pharmacol       Date:  2002-12       Impact factor: 4.436

6.  Simple conversion of aromatic amines into azides.

Authors:  Qi Liu; Yitzhak Tor
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

7.  Direct synthesis of 1,5-disubstituted-4-magnesio-1,2,3-triazoles, revisited.

Authors:  Antoni Krasiński; Valery V Fokin; K Barry Sharpless
Journal:  Org Lett       Date:  2004-04-15       Impact factor: 6.005

8.  The cannabinoid CB1 antagonists SR 141716A and AM 251 suppress food intake and food-reinforced behavior in a variety of tasks in rats.

Authors:  P J McLaughlin; K Winston; L Swezey; A Wisniecki; J Aberman; D J Tardif; A J Betz; K Ishiwari; A Makriyannis; J D Salamone
Journal:  Behav Pharmacol       Date:  2003-12       Impact factor: 2.293

Review 9.  Cannabinoids: reward, dependence, and underlying neurochemical mechanisms--a review of recent preclinical data.

Authors:  Gianluigi Tanda; Steven R Goldberg
Journal:  Psychopharmacology (Berl)       Date:  2003-06-24       Impact factor: 4.530

10.  The cannabinoid receptor antagonist SR-141716 does not readily antagonize open-field effects induced by the cannabinoid receptor agonist (R)-methanandamide in rats.

Authors:  Torbjörn U C Järbe; Nicholas V DiPatrizio; Chen Li; Alexandros Makriyannis
Journal:  Pharmacol Biochem Behav       Date:  2003-07       Impact factor: 3.533

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  4 in total

1.  In silico investigation of interactions between human cannabinoid receptor-1 and its antagonists.

Authors:  Guanglin Kuang; Guoping Hu; Xianqiang Sun; Weihua Li; Guixia Liu; Yun Tang
Journal:  J Mol Model       Date:  2012-03-09       Impact factor: 1.810

2.  Synthesis and antiprotozoal activity of cationic 1,4-diphenyl-1H-1,2,3-triazoles.

Authors:  Stanislav A Bakunov; Svetlana M Bakunova; Tanja Wenzler; Maedot Ghebru; Karl A Werbovetz; Reto Brun; Richard R Tidwell
Journal:  J Med Chem       Date:  2010-01-14       Impact factor: 7.446

3.  Neglected disease - african sleeping sickness: recent synthetic and modeling advances.

Authors:  Sarvesh K Paliwal; Ankita Narayan Verma; Shailendra Paliwal
Journal:  Sci Pharm       Date:  2011-05-10

4.  4-(4-Acetyl-5-methyl-1H-1,2,3-triazol-1-yl)benzo-nitrile: crystal structure and Hirshfeld surface analysis.

Authors:  Julio Zukerman-Schpector; Cássio da S Dias; Ricardo S Schwab; Mukesh M Jotani; Edward R T Tiekink
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2018-08-10
  4 in total

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