Synthesis and biological evaluation of novel 1-deoxy-1-[6-[((hetero) arylcarbonyl)hydrazino]-9H-purin-9-yl]-N-ethyl-β-D-ribofuranuronamide derivatives as useful templates for the development of A2B adenosine receptor agonists

Journal of Medicinal Chemistry

Volumn 50, Issue 2, 2007, Pages 374-380

  Baraldi, Pier Giovanni ^a   Preti, Delia ^a   Tabrizi, Mojgan Aghazadeh ^a   Fruttarolo, Francesca ^a   Romagnoli, Romeo ^a   Carrion, Maria Dora ^a   Lopez Cara, Luisa Carlota ^a   Moorman, Allan R ^b   Varani, Katia ^a   Borea, Pier Andrea ^a  

^a UNIVERSITY OF FERRARA   (Italy)

^b King Pharmaceuticals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXY 1 [6 [N' (FURAN 2 CARBONYL)HYDRAZINO] 9H PURIN 9 YL] N ETHYL BETA DEXTRO RIBOFURANURONAMIDE DERIVATIVE; ADENOSINE; ADENOSINE 5' (N ETHYLCARBOXAMIDE); ADENOSINE A2 RECEPTOR ANTAGONIST; ADENOSINE A2B RECEPTOR; ADENOSINE A2B RECEPTOR ANTAGONIST; CYCLIC AMP; UNCLASSIFIED DRUG;

AGONIST; ANIMAL CELL; ARTICLE; BIOLOGICAL ACTIVITY; CHO CELL; CONTROLLED STUDY; DOSE RESPONSE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

ADENOSINE; ANIMALS; BINDING, COMPETITIVE; CHO CELLS; CRICETINAE; CRICETULUS; CYCLIC AMP; HUMANS; HYDRAZINES; RADIOLIGAND ASSAY; RECEPTOR, ADENOSINE A2B; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33846435335     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061170a     Document Type: Article

References (44)

1. Klinger, M.; Freissmuth, M.; Nanoff, C. Adenosine receptors: G protein-mediated signalling and the role of accessory proteins. Cell. Signalling 2002, 14, 99-108.
2. Daly, J. W.; Butts-Lamb, P.; Padgett, W. Subclasses of adenosine receptors in the central nervous system: interaction with caffeine and related methylxanthines. Cell. Mol. Neurobiol. 1983, 3, 69-80.
3. 2-adenosine receptor subtype. Mol. Endocrinology 1992, 6, 384-393.
4. 2B receptors. Pharmacol. Rev. 1997, 49, 381-402.
5. Fredholm, B. B.; Ijzerman, A. P.; Jacobson, K. A.; Klotz, K. N.; Linden, J. International Union of Pharmacology. XXV. Nomenclature and classification of adenosine receptors. Pharmacol. Rev. 2001, 53, 527-552.
6. 2B receptor activation promotes glycogen synthesis in astrocytes through the modulation of gene expression. Am. J. Physiol.: Cell Physiol. 2003, 284 (3), C696-C704.
7. 2B adenosine receptors in the U87MG tumour cells. Drug Dev. Res. 2003, 58, 405-411.
8. Marx, D.; Ezeamuzie, C. I.; Nieber, K.; Szenlenyi, I. Therapy of bronchial asthma with adenosine receptor agonists and antagonists. Drug News Perspect. 2001, 14, 89-100.
9. 2B receptors. Circulation 1997, 96, 2656-2666.
10. 2B receptors. Hypertension 1998, 31, 516-521.
11. 2B purinoceptor. Circ. Res. 2000, 86, 76-85.
12. Le Vraux, V.; Chen, Y. L.; Masson, I.; De Sousa, M.; Giroud, J. P.; Florentin, I.; Chauvelot-Moachon, L. Inhibition of human monocyte TNF production by adenosine receptor agonists. Life Sci. 1993, 52, 1917-1924.
13. 2B receptor-coupled pathway. Am. J. Physiol.: Cell Physiol. 1999, 276, C361-C369.
14. Chiang, P. H.; Wu, S. N.; Tsai, E. M. Adenosine modulation of neurotransmission in penile erection. Br. J. Clin. Pharmacol. 1994, 38, 357-362.
15. Hancock, D. L.; Coupar, I. M. Functional characterization of the adenosine receptor mediating inhibition of intestinal secretion. Br. J. Pharmacol. 1995, 114, 152-166.
16. 2B receptors. Br. J. Pharmacol. 1999, 126, 1796-1800.
17. 2B adenosine receptor subtype. Curr. Med. Chem., in press.
18. 2B receptor: search for potent agonists. Nucleosides Nucleotides 1998, 17, 969-985.
19. Klotz, K. N.; Hessling, J.; Hegler, J.; Owman, B.; Kull, B.; Fredholm, B. B.; Lohse, M. J. Comparative pharmacology of human adenosine subtypes. Characterization of stably transfected receptors in CHO cells. Naunyn-Schmiedeberg's Arch. Pharmacol. 1998, 357, 1-9.
20. 2B receptors. Drug Dev. Res. 2000, 49, 85-93.
21. Rosentreter, U.; Kraemer, T.; Shimada, M.; Huebsch, W.; Diedrichs, N.; Krahn, T.; Henninger, K.; Stasch, J.-P. Substituted 2-thio-3,5-dicyano-4-phenyl- 6-aminopyridines and their use as adenosine receptor-selective ligands. PCT Int. Appl. WO 03008384, 2003.
22. 2B receptor with an improved selectivity profile compared to the reference agonist N-ethylcarboxamidoadenosine. J. Med. Chem. 2004, 47, 3707-3709.
23. 3 adenosine receptors. J. Med. Chem. 1996, 39, 802-806.
24. 3 adenosine receptor agonists. J. Med. Chem. 1998, 41, 3174-3185.
25. 3 adenosine receptor agonists. J. Med. Chem. 2004, 47, 5535-5540.
26. 2A receptors. Bioorg. Med. Chem. Lett. 1997, 7, 3085-3090.
27. 1 selective adenosine receptor agonists containing 6-hydrazinopurine moieties. Bioorg. Med. Chem. Lett. 1993, 3, 2661-2666.
28. 2-selective adenosine agonists. J. Med. Chem. 1994, 37, 636-646.
29. Nair, V.; Richardson, S. G. Modification of nucleic acid bases via radical intermediates: synthesis of dihalogenated purine nucleosides. Synthesis 1982, 670-672.
30. Sung, K.; Lee, A.-R. Synthesis of [(4,5-disubstituted-4H-1,2,4- triazol-3-yl)thio]alkanoic acids and their analogues as possible antiinflammatory agents. J. Heterocycl. Chem. 1992, 29, 1101-1109.
31. 3 adenosine receptors. Mol. Pharmacol. 2000, 57, 968-975.
32. 2B adenosine receptor subtypes: a molecular modeling investigation. J. Med. Chem. 2003, 46, 4287-4296.
33. 2B adenosine receptor agonists: synthesis and biological evaluation of 2-phenylhydroxypropynyl adenosine and NECA derivatives. Nucleosides Nucleotides Nucleic Acids 2004, 23, 471-481.
34. 2 adenosine receptor subtype. Nucleosides Nucleotides Nucleic Acids 2003, 22, 809-812.
35. 2 adenosine receptors. Curr. Top. Med. Chem. 2003, 3, 427-43.
36. 3H]-MRE 2029F20. Mol. Pharmacol. 2005, 67, 1-11.
37. Klotz, K. N.; Hessling, J.; Hegler, J.; Owman, C.; Kull, B.; Fredholm, B. B.; Lohse, M. J. Comparative pharmacology of human adenosine receptor subtypes. Characterization of stably transfected receptors in CHO cells. Naunyn Schmiedeberg's Arch. Pharmacol. 1998, 357, 1-9.
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, 7, 248-254.
39. 2A adenosine receptors. Life Sci. 1996, 59, 1373-1388.
40. 2A receptor ligands. Biochem. Pharmacol. 1995, 49, 461-469.
41. 2A adenosine receptors in human neutrophil membranes. Br. J. Pharmacol. 1998, 123, 1723-1731.
42. 50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 1, 3099-108.
43. Munson, P. J.; Rodbard, D. Ligand: a versatile computerized approach for characterization of ligand-binding systems. Anal. Biochem. 1980, 107, 220-39.
44. Biagi, G. L.; Barbaro, A. M.; Guerra, M. C.; Borea, P. A.; Pietrogrande, M. C. Study of the lipophilic character of xanthine and adenosine derivatives. J. Chromatogr. 1990, 498, 179-190.