A new synthesis of 2,8-disubstituted pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidines

Tetrahedron Letters

Volumn 50, Issue 40, 2009, Pages 5617-5621

  Dolzhenko, Anton V ^a   Pastorin, Giorgia ^a   Dolzhenko, Anna V ^a   Chui, Wai Keung ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

5 AMINO 4 IMINOPYRAZOLO[3,4 D]PYRIMIDINE; ACETOACETIC ACID DERIVATIVE; ADENOSINE RECEPTOR BLOCKING AGENT; BENZALDEHYDE DERIVATIVE; IODOBENZENE; IODOBENZENE DIACETATE; PYRAZOLE DERIVATIVE; PYRAZOLO[4,3 E][1,2,4]TRIAZOLO[1,5 C]PYRIMIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; POLYMERIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

HUMAN ECHOVIRUS 1;

EID: 68749116414     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.113     Document Type: Article

References (38)

1. For recent reviews on the therapeutic potential of adenosine receptor modulation, see:. Jacobson K.A., and Gao Z.G. Nat. Rev. Drug Disc. 5 (2006) 247-264
2. Wilson C.N. Br. J. Pharmacol. 155 (2008) 475-486
3. Hasko G., Linden J., Cronstein B., and Pacher P. Nat. Rev. Drug Disc. 7 (2008) 759-770
4. Vass G., and Horvath I. Curr. Med. Chem. 15 (2008) 917-922
5. Boison D. Curr. Opin. Pharmacol. 8 (2008) 2-7
6. Benarroch E.E. Neurology 70 (2008) 231-236
7. For recent reviews on adenosine receptor antagonists, see:. Moro S., Gao Z.G., Jacobson K.A., and Spalluto G. Med. Res. Rev. 26 (2006) 131-159
8. Press N.J., Gessi S., Borea P.A., and Polosa R. Exp. Opin. Ther. Pat. 17 (2007) 979-991
9. Gonzalez M.P., Teran C., and Teijeira M. Med. Res. Rev. 28 (2008) 329-371
10. Takahashi R.N., Pamplona F.A., and Prediger R.D.S. Front. Biosci. 13 (2008) 2614-2632
11. Baraldi P.G., Tabrizi M.A., Gessi S., and Borea P.A. Chem. Rev. 108 (2008) 238-263
12. For reviews on pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine antagonists of adenosine receptors, see:. Baraldi P.G., Cacciari B., Borea P.A., Varani K., Pastorin G., Da Ros T., Tabrizi M.A., Fruttarolo F., and Spalluto G. Curr. Pharm. Des. 8 (2002) 2299-2332
13. Baraldi P.G., Tabrizi M.A., Romagnoli R., Fruttarolo F., Merighi S., Varani K., Gessi S., and Borea P.A. Curr. Med. Chem. 12 (2005) 1319-1329
14. Baraldi P.G., Romagnoli R., El-Kashef H., Tabrizi M.A., Preti D., Pavani M.G., Zanella L., and Fruttarolo F. Targets Heterocycl. Syst. 10 (2006) 175-196
15. Baraldi P.G., Tabrizi M.A., Romagnoli R., El-Kashef H., Preti D., Bovero A., Fruttarolo F., Gordaliza M., and Borea P.A. Curr. Org. Chem. 10 (2006) 259-275
16. Cacciari B., Bolcato C., Spalluto G., Klotz K.N., Bacilieri M., Deflorian F., and Moro S. Purinergic Signalling 3 (2007) 183-193
17. Bolcato C., Cusan C., Pastorin G., Spalluto G., Cacciari B., Klotz K.N., Morizzo E., and Moro S. Purinergic Signalling 4 (2008) 39-46
18. Gatta F., Del Giudice M.R., Borioni A., Borea P.A., Dionisotti S., and Ongini E. Eur. J. Med. Chem. 28 (1993) 569-576
19. 2), 84.0, 113.7, 137.3 (CH), 156.6, 159.2 (CH).
20. Baraldi P.G., Manfredini S., Simoni D., Zappaterra L., Zocchi C., Dionisotti S., and Ongini E. Bioorg. Med. Chem. Lett. 4 (1994) 2539-2544
21. Baraldi P.G., El-Kashef H., Farghaly A.R., Vanelle P., and Fruttarolo F. Tetrahedron 60 (2004) 5093-5104
22. Dolzhenko A.V., Pastorin G., Dolzhenko A.V., Tan G.K., and Koh L.L. Acta Cryst. 65E (2009) o1578-o1579
23. 6): δ 38.8 (2Me), 100.4 (2C), 130.6 (2CH), 138.1 (2CH), 147.6 (2C), 152.2 (2C).
24. 6): δ 39.5 (Me), 105.4, 128.3 (CH), 149.9 (CH), 151.7 (br s), 155.0. Additionally, 7 (6-8%) precipitated from the filtrate on standing overnight.
25. For recent reviews on organic hypervalent iodine reagents, see:. Koser G.F. Adv. Heterocycl. Chem. 86 (2004) 225-292
26. Wirth T. Angew. Chem., Int. Ed. 44 (2005) 3656-3665
27. Richardson R.D., and Wirth T. Angew. Chem., Int. Ed. 45 (2006) 4402-4404
28. Matveeva E.D., Proskurnina M.V., and Zefirov N.S. Heteroat. Chem. 17 (2006) 595-617
29. Zhdankin V.V. Sci. Synth. 31a (2007) 161-233
30. Zhdankin V.V., and Stang P.J. Chem. Rev. 108 (2008) 5299-5358
31. For reviews on iodobenzene diacetate, see:. Varvoglis A. Chem. Soc. Rev. 10 (1981) 377-407
32. Prakash O., and Singh S.P. Aldrichimica Acta 27 (1994) 15-23
33. Kirschning A. J. Prakt. Chem. 340 (1998) 184-186
34. 2), 101.5, 112.6 (CH), 117.3 (CH), 119.4 (CH), 126.2 (CH), 127.5 (2CH), 127.8 (CH), 128.4 (2CH), 130.2 (CH), 131.1, 136.8, 139.8 (CH), 148.4, 153.7, 158.7, 162.9.
35. Taylor Jr. E.C., and Loeffler P.K. J. Am. Chem. Soc. 82 (1960) 3147-3151
36. Baraldi P.G., Cacciari B., Spalluto G., Pineda de Villatoro M.J., Zocchi C., Dionisotti S., and Ongini E. J. Med. Chem. 39 (1996) 1164-1171
37. 6): δ 33.2 and 33.3* (Me), 98.5, 130.8* and 134.6 (two br s, CH), 152.2* and 153.6 (two br s), 155.0 and 155.5* (two br s, CH), 156.8* and 160.5 (two br s). *-signals of minor hydrazone tautomer.
38. Dolzhenko A.V., Pastorin G., Dolzhenko A.V., Tan G.K., and Koh L.L. Acta Cryst. 65E (2009) o1720-o1721