Structure-activity relationships of truncated C2- or C8-substituted adenosine derivatives as dual acting A 2A and A 3 adenosine receptor ligands

Journal of Medicinal Chemistry

Volumn 55, Issue 1, 2012, Pages 342-356

  Hou, Xiyan ^a   Majik, Mahesh S ^a   Kim, Kyunglim ^a   Pyee, Yuna ^b   Lee, Yoonji ^a   Alexander, Varughese ^a   Chung, Hwa Jin ^b   Lee, Hyuk Woo ^a   Chandra, Girish ^a   Lee, Jin Hee ^a   Park, Seul Gi ^a   Choi, Won Jun ^a,c   Kim, Hea Ok ^a   Phan, Khai ^d   Gao, Zhan Guo ^d   Jacobson, Kenneth A ^d   Choi, Sun ^a   Lee, Sang Kook ^b   Jeong, Lak Shin ^a  

^a Ewha Womans University   (South Korea)

^b Seoul National University   (South Korea)

^c Dongguk University   (South Korea)

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

Author keywords

[No Author keywords available]

Indexed keywords

2 (6 AMINO 2 HEXY1 9H PURINE 9 YL)TETRAHYDROFURAN 3,4 DIOL; 2 (6 AMINO 2 HEXY1 9H PURINE 9 YL)TETRAHYDROTHIOPHEN 3,4 DIOL; 2 (TRIBUTYLSTANNYL) 6 CHLORO 9 (TETRAHYDRO 2,2 DIMETHYLFURO[3,4 D][1,3]DIOXOL 6 YL) 9H PURINE; 2 [6 CHLORO 2 (HEX 1 YNYL) 9H PURIN 9 YL]TETRAHYDROFURAN 3,4 DIOL; 2 [6 CHLORO 2 (HEX 1 YNYL) 9H PURIN 9 YL]TETRAHYDROTHIOPHENE 3,4 DIOL; 2 [[6 (3 BROMOBENZYLAMINO) 2 (HEX 1 YNYL) 9H PURIN 9 YL]]TETRAHYDROFURAN 3,4 DIOL; 2 [[6 (3 BROMOBENZYLAMINO) 2 (HEX 1 YNYL) 9H PURIN 9 YL]]TETRAHYDROTHIOPHENE 3,4 DIOL; 2 [[6 (3 CHLOROBENZYLAMINO) 2 (HEX 1 YNYL) 9H PURIN 9 YL]]TETRAHYDROFURAN 3,4 DIOL; 2 [[6 (3 FLUOROBENZYLAMINO) 2 (HEX 1 YNYL) 9H PURIN 9 YL]]TETRAHYDROFURAN 3,4 DIOL; 2 [[6 (3 FLUOROBENZYLAMINO) 2 (HEX 1 YNYL) 9H PURIN 9 YL]]TETRAHYDROTHIOPHENE 3,4 DIOL; 2 [[6 (3 IODOBENZYLAMINO) 2 (HEX 1 YNYL) 9H PURIN 9 YL]]TETRAHYDOFURAN 3,4 DIOL; 2 [[6 (3 IODOBENZYLAMINO) 2 (HEX 1 YNYL) 9H PURIN 9 YL]]TETRAHYDROTHIOPHENE 3,4 DIOL; 2 [[6 AMINO 2 (HEX 1 ENYL) 9H PURIN 9 YL]]TETRAHYDROFURAN 3,4 DIOL; 2 [[6 AMINO 2 (HEX 1 ENYL) 9H PURINE 9 YL]]TETRAHYDROTHIOPHENE 3,4 DIOL; 2 [[6 AMINO 8 (HEX 1 ENYL) 9H PURINE 9 YL]]TETRAHYDROFURAN 3,4 DIOL; 2 [[6 AMINO 8 (HEX 1 ENYL) 9H PURINE 9 YL]]TETRAHYDROTHIOPHENE 3,4 DIOL; 2 [[6 AMINO 8 (HEX 1 YNYL) 9H PURINE 9 YL]]TETRAHYDROTHIOPHENE 3,4 DIOL; 6 CHLORO 9 (2,2 DIMETHYLTETRAHYDROTHIENO[3,4 D][1,3]DIOXOL 4 YL 2 (HEX 1 YNYL) 9H PURINE; 6 CHLORO 9 (2,2 DIMETHYLTETRAHYDROTHIENO[3,4 D][1,3]DIOXOL 4 YL 2 IODO 9H PURINE; 6 CHLORO 9 (TETRAHYDRO 2,2 DIMETHYLFURO[3,4 D][1,3]DIOXOL 6 YL) 9H PURINE; 8 BROMO 9 (TETRAHYDRO 2,2 DIMETHYLFURO [3,4 D][1,3]DIOXOL 6 YL) 9H PURIN 6 AMINE; 9 (TETRAHYDRO 2,2 DIMETHYLFURO[3,4 D][1,3] DIOXOL 6 YL) 9H PURIN 6 AMINE; ADENOSINE A2A RECEPTOR; ADENOSINE A2A RECEPTOR AGONIST; ADENOSINE A3 RECEPTOR; ADENOSINE A3 RECEPTOR ANTAGONIST; ADENOSINE DERIVATIVE; CYCLIC AMP; PALLADIUM; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; ASTHMA; BINDING AFFINITY; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG POTENCY; EMBRYO; HUMAN; HUMAN CELL; LITHIATION; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

ADENOSINE; ADENOSINE A2 RECEPTOR AGONISTS; ADENOSINE A3 RECEPTOR ANTAGONISTS; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CHO CELLS; CRICETINAE; CRICETULUS; CYCLIC AMP; HEK293 CELLS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIGANDS; MALE; MODELS, MOLECULAR; RADIOLIGAND ASSAY; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, ADENOSINE A3; RECEPTORS, ADENOSINE A2; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES;

EID: 84862958304     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201229j     Document Type: Article

References (45)

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. 3 adenosine receptor ligands: history and perspectives Med. Res. Rev. 2000, 20, 103-128
4. Jacobson, K. A.; Gao, Z.-G. Adenosine receptors as therapeutic targets Nat. Rev. Drug Discovery 2006, 5, 247-264
5. 3 adenosine receptors J. Med. Chem. 1994, 37, 3614-3621
6. 3 adenosine receptor J. Med. Chem. 2003, 46, 3775-3777
7. 3 adenosine receptor J. Med. Chem. 2006, 49, 273-281
8. 1 cell cycle arrest and apoptosis in human promyelocytic leukemia HL-60 cells Biochem. Pharmacol. 2005, 70, 918-924
9. 3 adenosine receptor agonist CF102 induces apoptosis of hepatocellular carcinoma via de-regulation of the Wnt and NF-κB signal transduction pathways Int. J. Oncol. 2008, 33, 287-295
10. 3 receptor agonists Biochem. Biophys. Res. Commun. 1996, 219, 904-910
11. 3 adenosine receptor: analysis of binding and relative efficacy J. Chem. Inf. Model. 2007, 47, 1225-1231
12. 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
13. 3 adenosine receptor antagonists J. Med. Chem. 2008, 51, 6609-6613
14. 3 adenosine receptor antagonists Bioorg. Med. Chem. 2009, 17, 3733-3738
15. 3 adenosine receptors J. Med. Chem. 1995, 38, 1720-1735
16. 3 adenosine receptors lower mouse intraocular pressure and act across species Exp. Eye Res. 2010, 90, 146-154
17. 2A adenosine receptor agonist, truncated 2-hexynyl-4′- thioadenosine ACS Med. Chem. Lett. 2010, 1, 516-520
18. 2A receptors Annu. Rev. Immunol. 2004, 22, 657-682
19. 2A agonists in development for the treatment of inflammation Expert Opin. Invest. Drugs 2005, 14, 797-806
20. Kato, K.; Hayakawa, H.; Tanaka, H.; Kumamoto, H.; Shindoh, S.; Shuto, S.; Miyasaka, T. A new entry to 2-substituted purine nucleosides based on lithiation-mediated stannyl transfer of 6-chloropurine nucleosides J. Org. Chem. 1997, 62, 6833-6841
21. Brun, V.; Legraverend, M.; Grierson, D. S. Cyclin-dependent kinase (CDK) inhibitors: development of a general strategy for the construction of 2,6,9-trisubstituted purine libraries. Part 1 Tetrahedron Lett. 2001, 42, 8161-8164
22. Taddei, D.; Kilian, P.; Slawin, A. M. Z.; Woollins, D. Synthesis and full characterization of 6-chloro-2-iodopurine, a template for the functionalisation of purines Org. Biomol. Chem. 2004, 2, 665-670
23. Chinchilla, R.; Nájera, C. The Sonogashira reaction: a booming methodology in synthetic organic chemistry Chem. Rev. 2007, 107, 874-922
24. Suzuki, A. Carbon-carbon bonding made easy Chem. Commun. 2005, 38, 4759-4763
25. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1 Z,3 E)-1-Phenyl-1,3-octadiene. In Organic Syntheses; Wiley & Sons: New York, 1993; Collect. Vol. 8, pp 532-534.
26. 15N NMR spectroscopy and theoretical calculations J. Org. Chem. 2001, 66, 5463-5481
27. 3 adenosine receptor antagonists J. Med. Chem. 2005, 48, 4910-4918
28. 2 receptors in rat brain J. Pharmacol. Exp. Ther. 1989, 251, 888-893
29. 3 adenosine receptor Mol. Pharmacol. 1994, 45, 978-982
30. 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
31. 2 receptor agonists with potent antihypertensive effects J. Med. Chem. 1992, 35, 241-252
32. 2 adenosine receptor agonists with potent inhibitory activity on platelet aggregation J. Med. Chem. 1994, 37, 1720-1726
33. 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
34. 3 receptor antagonist activity Eur. J. Pharmacol. 2007, 564, 219-225
35. Morris, C. J. Casrrageenan-induced pawedema in the rat and mouse Methods Mol. Biol. 2003, 225, 115-121
36. Otterness, I. G.; Moore, P. F. Carrageenan foot edema test Methods Enzymol. 1988, 162, 320-327
37. 2A adenosine receptor bound to an antagonist Science 2008, 322, 1211-1217
38. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 1976, 72, 248-254
39. Kecskés, A.; Tosh, D. K.; Wei, Q.; Gao, Z. G.; Jacobson, K. A. GPCR ligand dendrimer (GLiDe) conjugates: adenosine receptor interactions of a series of multivalent xanthine antagonists Bioconjugate Chem. 2011, 22, 1115-1127
40. 2 receptors in rat brain Pharmacol. Exp. Ther. 1989, 251, 888-893
41. 3 adenosine receptor Mol. Pharmacol. 1994, 45, 978-982
42. 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
43. Post, S. R.; Ostrom, R. S.; Insel, P. A. Biochemical methods for detection and measurement of cyclic AMP and adenylyl cyclase activity Methods Mol. Biol. 2000, 126, 363-374
44. Cheng, Y. C.; Prusoff, H. R. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction Biochem. Pharmacol. 1973, 22, 3099-3108
45. Yeşilada, E.; Köpeli, E. Berberis crataegina DC. root exhibits potent anti-inflammatory, analgesic and febrifuge effects in mice and rats J. Ethnopharmacol. 2002, 79, 237-248