Literature DB >> 28626532

Development of Quinazoline/Pyrimidine-2,4(1H,3H)-diones as Agonists of Cannabinoid Receptor Type 2.

Hai-Yan Qian1, Zhi-Long Wang2, You-Lu Pan1, Li-Li Chen1, Xin Xie2, Jian-Zhong Chen1.   

Abstract

Starting from a prototypical structure 1, we describe our efforts to design and obtain novel quinazoline/pyrimidine-2,4(1H,3H)-diones with high CB2 agonist potency and selectivity as well as improved physicochemical characteristics, mainly hydrophilicity. The most potent and selective CB2 agonists, 8 and 36, in this series were also endowed with lower logP values than that of GW842166X and lead compound 1. These derivatives appear to be promising lead compounds for the development of future CB2 agonists.

Entities:  

Keywords:  CB2 agonist; Cannabinoid receptors; molecular modeling; structure−activity relationship

Year:  2017        PMID： 28626532      PMCID： PMC5467194          DOI： 10.1021/acsmedchemlett.7b00007

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


  15 in total

1.  3-(1',1'-Dimethylbutyl)-1-deoxy-delta8-THC and related compounds: synthesis of selective ligands for the CB2 receptor.

Authors:  J W Huffman; J Liddle; S Yu; M M Aung; M E Abood; J L Wiley; B R Martin
Journal:  Bioorg Med Chem       Date:  1999-12       Impact factor: 3.641

2.  Rimonabant.

Authors:  Sheridan Henness; Dean M Robinson; Katherine A Lyseng-Williamson
Journal:  Drugs       Date:  2006       Impact factor: 9.546

Review 3.  Selective cannabinoid receptor 2 modulators: a patent review 2009--present.

Authors:  Doris Riether
Journal:  Expert Opin Ther Pat       Date:  2012-04-27       Impact factor: 6.674

4.  Reductions in log P improved protein binding and clearance predictions enabling the prospective design of cannabinoid receptor (CB1) antagonists with desired pharmacokinetic properties.

Authors:  Bruce A Ellsworth; Philip M Sher; Ximao Wu; Gang Wu; Richard B Sulsky; Zhengxiang Gu; Natesan Murugesan; Yeheng Zhu; Guixue Yu; Doree F Sitkoff; Kenneth E Carlson; Liya Kang; Yifan Yang; Ning Lee; Rose A Baska; William J Keim; Mary Jane Cullen; Anthony V Azzara; Eva Zuvich; Michael A Thomas; Kenneth W Rohrbach; James J Devenny; Helen E Godonis; Susan J Harvey; Brian J Murphy; Gerry G Everlof; Paul I Stetsko; Olafur Gudmundsson; Susan Johnghar; Asoka Ranasinghe; Kamelia Behnia; Mary Ann Pelleymounter; William R Ewing
Journal:  J Med Chem       Date:  2013-11-20       Impact factor: 7.446

5.  Development of Quinoline-2,4(1H,3H)-diones as Potent and Selective Ligands of the Cannabinoid Type 2 Receptor.

Authors:  Shuang Han; Fei-Fei Zhang; Hai-Yan Qian; Li-Li Chen; Jian-Bin Pu; Xin Xie; Jian-Zhong Chen
Journal:  J Med Chem       Date:  2015-07-23       Impact factor: 7.446

6.  Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 7. Synthesis and Pharmacological Evaluation of 4-Quinolone-3-carboxamides and 4-Hydroxy-2-quinolone-3-carboxamides as High Affinity Cannabinoid Receptor 2 (CB2R) Ligands with Improved Aqueous Solubility.

Authors:  Claudia Mugnaini; Antonella Brizzi; Alessia Ligresti; Marco Allarà; Stefania Lamponi; Federica Vacondio; Claudia Silva; Marco Mor; Vincenzo Di Marzo; Federico Corelli
Journal:  J Med Chem       Date:  2016-01-26       Impact factor: 7.446

7.  HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor.

Authors:  L Hanus; A Breuer; S Tchilibon; S Shiloah; D Goldenberg; M Horowitz; R G Pertwee; R A Ross; R Mechoulam; E Fride
Journal:  Proc Natl Acad Sci U S A       Date:  1999-12-07       Impact factor: 11.205

8.  A randomized, controlled study to investigate the analgesic efficacy of single doses of the cannabinoid receptor-2 agonist GW842166, ibuprofen or placebo in patients with acute pain following third molar tooth extraction.

Authors:  Thor Ostenfeld; Jeffrey Price; Massimo Albanese; Jonathan Bullman; Fiona Guillard; Ingo Meyer; Rachel Leeson; Cristina Costantin; Luigi Ziviani; Pier Francesco Nocini; Stefano Milleri
Journal:  Clin J Pain       Date:  2011-10       Impact factor: 3.442

9.  Discovery of 2-[(2,4-dichlorophenyl)amino]-N-[(tetrahydro- 2H-pyran-4-yl)methyl]-4-(trifluoromethyl)- 5-pyrimidinecarboxamide, a selective CB2 receptor agonist for the treatment of inflammatory pain.

Authors:  Gerard M P Giblin; Celestine T O'Shaughnessy; Alan Naylor; William L Mitchell; Andrew J Eatherton; Brian P Slingsby; D Anthony Rawlings; Paul Goldsmith; Andrew J Brown; Carl P Haslam; Nick M Clayton; Alex W Wilson; Iain P Chessell; Andrew R Wittington; Richard Green
Journal:  J Med Chem       Date:  2007-05-04       Impact factor: 7.446

10.  Development of a universal high-throughput calcium assay for G-protein- coupled receptors with promiscuous G-protein Galpha15/16.

Authors:  Ting Zhu; Li-yan Fang; Xin Xie
Journal:  Acta Pharmacol Sin       Date:  2008-04       Impact factor: 6.150
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  1 in total

1.  Acid-Catalyzed Synthesis of Isatoic Anhydride-8-Secondary Amides Enables IASA Transformations for Medicinal Chemistry.

Authors:  Sudershan R Gondi; Althaf Shaik; Kenneth D Westover
Journal:  J Org Chem       Date:  2021-12-28       Impact factor: 4.198
  1 in total

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