Literature DB >> 16190743

Discovery of potent 3,5-diphenyl-1,2,4-oxadiazole sphingosine-1-phosphate-1 (S1P1) receptor agonists with exceptional selectivity against S1P2 and S1P3.

Zhen Li1, Weirong Chen, Jeffrey J Hale, Christopher L Lynch, Sander G Mills, Richard Hajdu, Carol Ann Keohane, Mark J Rosenbach, James A Milligan, Gan-Ju Shei, Gary Chrebet, Stephen A Parent, James Bergstrom, Deborah Card, Michael Forrest, Elizabeth J Quackenbush, L Alexandra Wickham, Hugo Vargas, Rose M Evans, Hugh Rosen, Suzanne Mandala.   

Abstract

A class of 3,5-diphenyl-1,2,4-oxadiazole based compounds have been identified as potent sphingosine-1-phosphate-1 (S1P1) receptor agonists with minimal affinity for the S1P2 and S1P3 receptor subtypes. Analogue 26 (S1P1 IC50 = 0.6 nM) has an excellent pharmacokinetics profile in the rat and dog and is efficacious in a rat skin transplant model, indicating that S1P3 receptor agonism is not a component of immunosuppressive efficacy.

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Year:  2005        PMID： 16190743     DOI： 10.1021/jm0503244

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


  18 in total

Review 1.  International Union of Basic and Clinical Pharmacology. LXXVIII. Lysophospholipid receptor nomenclature.

Authors:  Jerold Chun; Timothy Hla; Kevin R Lynch; Sarah Spiegel; Wouter H Moolenaar
Journal:  Pharmacol Rev       Date:  2010-12       Impact factor: 25.468

Review 2.  Pharmacological tools for lysophospholipid GPCRs: development of agonists and antagonists for LPA and S1P receptors.

Authors:  Dong-Soon Im
Journal:  Acta Pharmacol Sin       Date:  2010-08-23       Impact factor: 6.150

Review 3.  Sphingosine-1-phosphate receptors: biology and therapeutic potential in kidney disease.

Authors:  S-K Jo; A Bajwa; A S Awad; K R Lynch; M D Okusa
Journal:  Kidney Int       Date:  2008-03-05       Impact factor: 10.612

4.  Synthesis of 2-(1,2,4-oxadiazol-3-yl)quinazolin-4(3H)-ones from diaminoglyoxime-based nitrones.

Authors:  Rahim Hosseinzadeh-Khanmiri; Abolghasem Moghimi; Ahmad Shaabani; Hassan Valizadeh; Seik Weng Ng
Journal:  Mol Divers       Date:  2015-04-22       Impact factor: 2.943

5.  Bis-aryloxadiazoles as effective activators of the aryl hydrocarbon receptor.

Authors:  Kaitlin J Basham; Vasudev R Bhonde; Collin Kieffer; James B C Mack; Matthew Hess; Bryan E Welm; Ryan E Looper
Journal:  Bioorg Med Chem Lett       Date:  2014-04-13       Impact factor: 2.823

6.  Identification of potent tricyclic prodrug S1P1 receptor modulators.

Authors:  David Marcoux; Hai-Yun Xiao; T G Murali Dhar; Jenny Xie; Lois D Lehman-McKeeman; Dauh-Rurng Wu; Marta Dabros; Xiaoxia Yang; Tracy L Taylor; Xia D Zhou; Elizabeth M Heimrich; Rochelle Thomas; Kim W McIntyre; Hong Shi; Paul C Levesque; Huadong Sun; Zheng Yang; Anthony M Marino; Georgia Cornelius; Celia J D'Arienzo; Anuradha Gupta; Bala Pragalathan; Richard Rampulla; Arvind Mathur; Ding Ren Shen; Mary Ellen Cvijic; Luisa Salter-Cid; Louis J Lombardo; Percy H Carter; Alaric J Dyckman
Journal:  Medchemcomm       Date:  2016-11-25       Impact factor: 3.597

7.  Identification and Preclinical Pharmacology of BMS-986104: A Differentiated S1P1 Receptor Modulator in Clinical Trials.

Authors:  T G Murali Dhar; Hai-Yun Xiao; Jenny Xie; Lois D Lehman-McKeeman; Dauh-Rurng Wu; Marta Dabros; Xiaoxia Yang; Tracy L Taylor; Xia D Zhou; Elizabeth M Heimrich; Rochelle Thomas; Kim W McIntyre; Bethanne Warrack; Hong Shi; Paul C Levesque; Jia L Zhu; James Hennan; Praveen Balimane; Zheng Yang; Anthony M Marino; Georgia Cornelius; Celia J D'Arienzo; Arvind Mathur; Ding Ren Shen; Mary Ellen Cvijic; Luisa Salter-Cid; Joel C Barrish; Percy H Carter; Alaric J Dyckman
Journal:  ACS Med Chem Lett       Date:  2016-01-19       Impact factor: 4.345

8.  Full pharmacological efficacy of a novel S1P1 agonist that does not require S1P-like headgroup interactions.

Authors:  Pedro J Gonzalez-Cabrera; Euijung Jo; M Germana Sanna; Steven Brown; Nora Leaf; David Marsolais; Marie-Therese Schaeffer; Jacqueline Chapman; Michael Cameron; Miguel Guerrero; Edward Roberts; Hugh Rosen
Journal:  Mol Pharmacol       Date:  2008-08-15       Impact factor: 4.436

9.  Rapid multistep synthesis of 1,2,4-oxadiazoles in a single continuous microreactor sequence.

Authors:  Daniel Grant; Russell Dahl; Nicholas D P Cosford
Journal:  J Org Chem       Date:  2008-08-08       Impact factor: 4.354

10.  FTY720 story. Its discovery and the following accelerated development of sphingosine 1-phosphate receptor agonists as immunomodulators based on reverse pharmacology.

Authors:  Kunitomo Adachi; Kenji Chiba
Journal:  Perspect Medicin Chem       Date:  2007-09-06
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