Literature DB >> 15615513

A rational utilization of high-throughput screening affords selective, orally bioavailable 1-benzyl-3-carboxyazetidine sphingosine-1-phosphate-1 receptor agonists.

Jeffrey J Hale1, Christopher L Lynch, William Neway, Sander G Mills, Richard Hajdu, Carol Ann Keohane, Mark J Rosenbach, James A Milligan, Gan-Ju Shei, Stephen A Parent, Gary Chrebet, James Bergstrom, Deborah Card, Marc Ferrer, Peter Hodder, Berta Strulovici, Hugh Rosen, Suzanne Mandala.   

Abstract

Moderately potent, selective S1P(1) receptor agonists identified from high-throughput screening have been adapted into lipophilic tails for a class of orally bioavailable amino acid-based S1P(1) agonists represented by 7. Many of the new compounds are potent S1P(1) agonists that select against the S1P(2), S1P(3), and S1P(4) (although not S1P(5)) receptor subtypes. Analogues 18 and 24 are highly orally bioavailable and possess excellent pharmacokinetic profiles in the rat, dog, and rhesus monkey.

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Year:  2004        PMID: 15615513     DOI: 10.1021/jm0492507

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


  18 in total

1.  Molecular recognition in the sphingosine 1-phosphate receptor family.

Authors:  Truc-Chi T Pham; James I Fells; Daniel A Osborne; E Jeffrey North; Mor M Naor; Abby L Parrill
Journal:  J Mol Graph Model       Date:  2007-11-17       Impact factor: 2.518

Review 2.  Modulators of the Sphingosine 1-phosphate receptor 1.

Authors:  Mariangela Urbano; Miguel Guerrero; Hugh Rosen; Edward Roberts
Journal:  Bioorg Med Chem Lett       Date:  2013-09-29       Impact factor: 2.823

3.  A practical process for the preparation of [(32)P]S1P and binding assay for S1P receptor ligands.

Authors:  Adam J Rosenberg; Hui Liu; Zhude Tu
Journal:  Appl Radiat Isot       Date:  2015-04-17       Impact factor: 1.513

4.  Discovery of a Selective S1P1 Receptor Agonist Efficacious at Low Oral Dose and Devoid of Effects on Heart Rate.

Authors:  Emmanuel H Demont; Benjamin I Andrews; Rino A Bit; Colin A Campbell; Jason W B Cooke; Nigel Deeks; Sapna Desai; Simon J Dowell; Pam Gaskin; James R J Gray; Andrea Haynes; Duncan S Holmes; Umesh Kumar; Mary A Morse; Greg J Osborne; Terry Panchal; Bela Patel; Alcide Perboni; Simon Taylor; Robert Watson; Jason Witherington; Robert Willis
Journal:  ACS Med Chem Lett       Date:  2011-03-24       Impact factor: 4.345

5.  4-Methoxy-N-[2-(trifluoromethyl)biphenyl-4-ylcarbamoyl]nicotinamide: A Potent and Selective Agonist of S1P1.

Authors:  Lewis D Pennington; Kelvin K C Sham; Alexander J Pickrell; Paul E Harrington; Michael J Frohn; Brian A Lanman; Anthony B Reed; Michael D Croghan; Matthew R Lee; Han Xu; Michele McElvain; Yang Xu; Xuxia Zhang; Michael Fiorino; Michelle Horner; Henry G Morrison; Heather A Arnett; Christopher Fotsch; Min Wong; Victor J Cee
Journal:  ACS Med Chem Lett       Date:  2011-07-29       Impact factor: 4.345

6.  Discovery of a Potent, S1P3-Sparing Benzothiazole Agonist of Sphingosine-1-Phosphate Receptor 1 (S1P1).

Authors:  Brian A Lanman; Victor J Cee; Srinivasa R Cheruku; Mike Frohn; Jennifer Golden; Jian Lin; Mercedes Lobera; Yael Marantz; Kristine M Muller; Susana C Neira; Alexander J Pickrell; Dalia Rivenzon-Segal; Nili Schutz; Anurag Sharadendu; Xiang Yu; Zhaoda Zhang; Janet Buys; Mike Fiorino; Anu Gore; Michelle Horner; Andrea Itano; Michele McElvain; Scot Middleton; Michael Schrag; Hugo M Vargas; Han Xu; Yang Xu; Xuxia Zhang; Jerry Siu; Roland W Bürli
Journal:  ACS Med Chem Lett       Date:  2010-11-09       Impact factor: 4.345

7.  Discovery of AMG 369, a Thiazolo[5,4-b]pyridine Agonist of S1P1 and S1P5.

Authors:  Victor J Cee; Mike Frohn; Brian A Lanman; Jennifer Golden; Kristine Muller; Susana Neira; Alex Pickrell; Heather Arnett; Janet Buys; Anu Gore; Mike Fiorino; Michelle Horner; Andrea Itano; Matt R Lee; Michele McElvain; Scot Middleton; Michael Schrag; Dalia Rivenzon-Segal; Hugo M Vargas; Han Xu; Yang Xu; Xuxia Zhang; Jerry Siu; Min Wong; Roland W Bürli
Journal:  ACS Med Chem Lett       Date:  2010-12-29       Impact factor: 4.345

8.  Benzofuran Derivatives as Potent, Orally Active S1P1 Receptor Agonists: A Preclinical Lead Molecule for MS.

Authors:  Ashis K Saha; Xiang Yu; Jian Lin; Mercedes Lobera; Anurag Sharadendu; Srinivas Chereku; Nili Schutz; Dalia Segal; Yael Marantz; Dilara McCauley; Scot Middleton; Jerry Siu; Roland W Bürli; Janet Buys; Michelle Horner; Kevin Salyers; Michael Schrag; Hugo M Vargas; Yang Xu; Michele McElvain; Han Xu
Journal:  ACS Med Chem Lett       Date:  2010-11-09       Impact factor: 4.345

9.  Asymmetric synthesis of conformationally constrained fingolimod analogues--discovery of an orally active sphingosine 1-phosphate receptor type-1 agonist and receptor type-3 antagonist.

Authors:  Ran Zhu; Ashley H Snyder; Yugesh Kharel; Lisa Schaffter; Qin Sun; Perry C Kennedy; Kevin R Lynch; Timothy L Macdonald
Journal:  J Med Chem       Date:  2007-11-10       Impact factor: 7.446

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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