Literature DB >> 25699149

Conformational Restriction Leading to a Selective CB2 Cannabinoid Receptor Agonist Orally Active Against Colitis.

Jamal El Bakali1, Giulio G Muccioli2, Mathilde Body-Malapel3, Madjid Djouina3, Frédérique Klupsch1, Alina Ghinet1, Amélie Barczyk1, Nicolas Renault1, Philippe Chavatte1, Pierre Desreumaux3, Didier M Lambert2, Régis Millet1.   

Abstract

The CB2 cannabinoid receptor has been implicated in the regulation of intestinal inflammation. Following on from the promising activity of a series of 4-oxo-1,4-dihydroquinoline-3-carboxamide, we developed constrained analogues based on a 2H-pyrazolo[4,3-c]quinolin-3(5H)-one scaffold, with improved affinity for the hCB2 receptor and had very high selectivity over the hCB1 receptor. Importantly, the lead of this series (26, hCB2: K i = 0.39 nM, hCB1: K i > 3000 nM) was found to protect mice against experimental colitis after oral administration.

Entities:  

Keywords:  Cannabinoid receptor; colitis; conformational restriction; endocannabinoid; inflammatory bowel disease; quinolone

Year:  2014        PMID： 25699149      PMCID： PMC4329582          DOI： 10.1021/ml500439x

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  17 in total

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Journal:  N Engl J Med       Date:  2002-08-08       Impact factor: 91.245

2.  4-Oxo-1,4-dihydropyridines as selective CB2 cannabinoid receptor ligands: structural insights into the design of a novel inverse agonist series.

Authors:  Jamal El Bakali; Giulio G Muccioli; Nicolas Renault; Delphine Pradal; Mathilde Body-Malapel; Madjid Djouina; Laurie Hamtiaux; Virginie Andrzejak; Pierre Desreumaux; Philippe Chavatte; Didier M Lambert; Régis Millet
Journal:  J Med Chem       Date:  2010-10-27       Impact factor: 7.446

3.  Agonists of cannabinoid receptor 1 and 2 inhibit experimental colitis induced by oil of mustard and by dextran sulfate sodium.

Authors:  Edward S Kimball; Craig R Schneider; Nathaniel H Wallace; Pamela J Hornby
Journal:  Am J Physiol Gastrointest Liver Physiol       Date:  2006-03-30       Impact factor: 4.052

4.  Cannabinoid receptor-2 (CB2) agonist ameliorates colitis in IL-10(-/-) mice by attenuating the activation of T cells and promoting their apoptosis.

Authors:  Udai P Singh; Narendra P Singh; Balwan Singh; Robert L Price; Mitzi Nagarkatti; Prakash S Nagarkatti
Journal:  Toxicol Appl Pharmacol       Date:  2011-11-18       Impact factor: 4.219

5.  Synthesis and biological evaluation of 2,5-dihydropyrazol.

Authors:  M I Crespo; J Gràcia; C Puig; A Vega; J Bou; J Beleta; T Doménech; H Ryder; V Segarra; J M Palacios
Journal:  Bioorg Med Chem Lett       Date:  2000-12-04       Impact factor: 2.823

6.  Activation of the cannabinoid 2 receptor (CB2) protects against experimental colitis.

Authors:  Martin A Storr; Catherine M Keenan; Hong Zhang; Kamala D Patel; Alexandros Makriyannis; Keith A Sharkey
Journal:  Inflamm Bowel Dis       Date:  2009-11       Impact factor: 5.325

Review 7.  The endocannabinoid system in inflammatory bowel diseases: from pathophysiology to therapeutic opportunity.

Authors:  Mireille Alhouayek; Giulio G Muccioli
Journal:  Trends Mol Med       Date:  2012-08-21       Impact factor: 11.951

8.  3-Quinolinecarboxamides. A series of novel orally-active antiherpetic agents.

Authors:  M P Wentland; R B Perni; P H Dorff; R P Brundage; M J Castaldi; T R Bailey; P M Carabateas; E R Bacon; D C Young; M G Woods
Journal:  J Med Chem       Date:  1993-05-28       Impact factor: 7.446

9.  New 1,8-naphthyridine and quinoline derivatives as CB2 selective agonists.

Authors:  Clementina Manera; Maria Grazia Cascio; Veronica Benetti; Marco Allarà; Tiziano Tuccinardi; Adriano Martinelli; Giuseppe Saccomanni; Elisa Vivoli; Carla Ghelardini; Vincenzo Di Marzo; Pier Luigi Ferrarini
Journal:  Bioorg Med Chem Lett       Date:  2007-10-01       Impact factor: 2.823

10.  Attenuation of colon inflammation through activators of the retinoid X receptor (RXR)/peroxisome proliferator-activated receptor gamma (PPARgamma) heterodimer. A basis for new therapeutic strategies.

Authors:  P Desreumaux; L Dubuquoy; S Nutten; M Peuchmaur; W Englaro; K Schoonjans; B Derijard; B Desvergne; W Wahli; P Chambon; M D Leibowitz; J F Colombel; J Auwerx
Journal:  J Exp Med       Date:  2001-04-02       Impact factor: 14.307
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1.  Structure-Guided Design of Novel, Potent, and Selective Macrocyclic Plasma Kallikrein Inhibitors.

Authors:  Zhe Li; James Partridge; Abel Silva-Garcia; Peter Rademacher; Andreas Betz; Qing Xu; Hing Sham; Yunjin Hu; Yuqing Shan; Bin Liu; Ying Zhang; Haijuan Shi; Qiong Xu; Xubo Ma; Li Zhang
Journal:  ACS Med Chem Lett       Date:  2016-12-06       Impact factor: 4.345

Review 2.  Manipulation of the Endocannabinoid System in Colitis: A Comprehensive Review.

Authors:  Kristina L Leinwand; Mark E Gerich; Edward J Hoffenberg; Colm B Collins
Journal:  Inflamm Bowel Dis       Date:  2017-02       Impact factor: 5.325

Review 3.  The Endocannabinoid System and Heart Disease: The Role of Cannabinoid Receptor Type 2.

Authors:  Makenzie L Fulmer; Douglas P Thewke
Journal:  Cardiovasc Hematol Disord Drug Targets       Date:  2018

4.  Endocannabinoids Inhibit the Induction of Virulence in Enteric Pathogens.

Authors:  Melissa Ellermann; Alline R Pacheco; Angel G Jimenez; Regan M Russell; Santiago Cuesta; Aman Kumar; Wenhan Zhu; Gonçalo Vale; Sarah A Martin; Prithvi Raj; Jeffrey G McDonald; Sebastian E Winter; Vanessa Sperandio
Journal:  Cell       Date:  2020-10-07       Impact factor: 41.582

Review 5.  The CB2 receptor and its role as a regulator of inflammation.

Authors:  Caroline Turcotte; Marie-Renée Blanchet; Michel Laviolette; Nicolas Flamand
Journal:  Cell Mol Life Sci       Date:  2016-07-11       Impact factor: 9.261

Review 6.  Intestinal Autophagy and Its Pharmacological Control in Inflammatory Bowel Disease.

Authors:  Ping Ke; Bo-Zong Shao; Zhe-Qi Xu; Xiong-Wen Chen; Chong Liu
Journal:  Front Immunol       Date:  2017-01-09       Impact factor: 7.561

Review 7.  Cannabis, Cannabinoids, and the Endocannabinoid System-Is there Therapeutic Potential for Inflammatory Bowel Disease?

Authors:  Tim Ambrose; Alison Simmons
Journal:  J Crohns Colitis       Date:  2019-03-30       Impact factor: 9.071

8.  Cannabinoid Receptor-2 Ameliorates Inflammation in Murine Model of Crohn's Disease.

Authors:  Kristina L Leinwand; Ashleigh A Jones; Rick H Huang; Paul Jedlicka; Daniel J Kao; Edwin F de Zoeten; Soumita Ghosh; Ruin Moaddel; Jan Wehkamp; Maureen J Ostaff; Jutta Bader; Carol M Aherne; Colm B Collins
Journal:  J Crohns Colitis       Date:  2017-10-27       Impact factor: 9.071
  8 in total

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