Discovery of a new human A2A adenosine receptor agonist, truncated 2-hexynyl-4′-thioadenosine

ACS Medicinal Chemistry Letters

Volumn 1, Issue 9, 2010, Pages 516-520

  Hou, Xiyan ^a   Kim, Hea Ok ^a   Alexander, Varughese ^a   Kim, Kyunglim ^a   Choi, Sun ^a   Park, Seul Gi ^a   Lee, Jin Hee ^a   Yoo, Lena S ^b   Gao, Zhan Guo ^b   Jacobson, Kenneth A ^b   Jeong, Lak Shin ^a  

^a Ewha Womans University   (South Korea)

^b NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

A2A adenosine receptor agonists; binding mode; palladium catalyzed cross coupling reactions; truncated 2 hexynyl 4 thioadenosine

Indexed keywords

2 [4 (2 CARBOXYETHYL)PHENETHYLAMINO]ADENOSINE 5' (N ETHYLCARBOXAMIDE); 2 HEXYNYL 4' THIOADENOSINE; 8 HEXENYL 4' THIO ADENOSINE DERIVATIVE; ADENOSINE A2A RECEPTOR AGONIST; ADENOSINE DERIVATIVE; MANNOSE; PALLADIUM; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; DRUG BINDING SITE; FEMALE; HUMAN; HUMAN CELL; NONHUMAN; PRIORITY JOURNAL; SUZUKI REACTION; SYNTHESIS;

EID: 78650212574     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml1001823     Document Type: Article

References (28)

1. Olah, M. E.; Stiles, G. L. The role of receptor structure in determining adenosine receptor activity Pharmacol. Ther. 2000, 85, 55-75
2. Fredholm, B. B.; Cunha, R. A.; Svenningsson, P. Pharmacology of adenosine receptors and therapeutic applications Curr. Top. Med. Chem. 2002, 3, 413-426
3. 2A receptors Annu. Rev. Immunol. 2004, 22, 657-682
4. 2A agonists in development for the treatment of inflammation Expert Opin. Invest. Drugs 2005, 14, 797-806
5. Svenningsson, P.; Hall, H.; Sedvall, G.; Fredholm, B. B. Distribution of adenosine receptors in the postmortem human brain: An extended autoradiographic study Synapse 1997, 27, 322-335
6. 3 receptors: Pharmacological properties, species differences and receptor functions Trends Pharmacol. Sci. 1994, 15, 298-306
7. 3 adenosine receptor ligands: History and perspectives Med. Res. Rev. 2000, 20, 103-128
8. Jacobson, K. A.; Gao, Z.-G. Adenosine receptors as therapeutic targets Nature Rev. Drug Discovery 2006, 5, 247-264
9. 3 adenosine receptor J. Med. Chem. 2003, 46, 3775-3777
10. 3 adenosine receptor J. Med. Chem. 2006, 49, 273-281
11. 3 adenosine receptors J. Med. Chem. 1994, 37, 3614-3621
12. 1 cell cycle arrest and apoptosis in human promyelocytic leukemia HL-60 cells Biochem. Pharmacol. 2005, 70, 918-924
13. 3 adenosine receptor ligands: D-4′-thioadenosine derivatives without 4′-hydroxymethyl group as highly potent and selective antagonists J. Med. Chem. 2007, 50, 3159-3162
14. 3 adenosine receptor antagonists J. Med. Chem. 2008, 51, 6609-6613
15. 2 receptor agonists with potent antihypertensive effects J. Med. Chem. 1992, 35, 241-252
16. 2 adenosine receptor agonists with potent inhibitory activity on platelet aggregation J. Med. Chem. 1994, 37, 1720-1726
17. Lambertucci, C.; Costanzi, S.; Vittori, S.; Volpini, R.; Cristalli, G. Synthesis and adenosine receptor affinity and potency of 8-alkynyl derivatives of adenosine Nucleosides, Nucleotides Nucleic Acids 2001, 20, 1153-1157
18. Chinchilla, R.; Nájera, C. The Sonogashira reaction: A booming methodology in synthetic organic chemistry Chem. Rev. 2007, 107, 874-922
19. Suzuki, A. Carbon-carbon bonding made easy Chem. Commun. 2005, 38, 4759-4763
20. Miyaura, N.; Suzuki, A. Palladium-catalyzed Reaction of 1-alkenylboronates with vinylic halides: (1 Z,3 E)-1-phenyl-1,3-octadiene Org. Syn. Coll. Vol. 1993, 8, 532-534
21. 15N NMR Spectroscopy and Theoretical Calculations J. Org. Chem. 2001, 66, 5463-5481
22. 3 Adenosine Receptor Antagonists J. Med. Chem. 2005, 48, 4910-4918
23. 2 receptors in rat brain J. Pharmacol. Exp. Ther. 1989, 251, 888-893
24. 3 adenosine receptor Mol. Pharmacol. 1994, 45, 978-982
25. Nordstedt, C.; Fredholm, B. B. A modification of a protein-binding method for rapid quantification of cAMP in cell-culture supernatants and body fluid Anal. Biochem. 1990, 189, 231-234
26. 3 receptor antagonist activity Eur. J. Pharmacol. 2007, 564, 219-225
27. 2A adenosine receptor bound to an antagonist Science 2008, 322, 1211-1217
28. GOLD, version 4.1.2; Cambridge Crystallographic Data Centre: Cambridge, United Kingdom, 2009.