Regioselective N- and O-Alkylation of 3H-[1,2,3]triazolo-[4,5-d]pyrimidine-5,7(4H,6H)-diones (8-azaxanthines) and transformation of 3-alkyl derivatives into 1-alkyl isomers

Heterocycles

Volumn 68, Issue 9, 2006, Pages 1811-1820

  Nagamatsu, Tomohisa ^a   Islam, Rafiqul ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751241430     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-06-10807     Document Type: Article

References (43)

1. Smith K.O., Galloway K.S., Kennell W.L., Ogilvie K.K., and Radatus B.K. Antimicrob. Agents Chemother. 22 (1982) 55
2. Smee D.F., Martin J.C., Verheyden J.P.H., and Matthews T.R. Antimicrob. Agents Chemother. 23 (1983) 676
3. Bonnet P.A., and Robins R.K. J. Med. Chem. 36 (1993) 635
4. Qin X., Chen X., Wang K., Polin L., Kern E.R., Drach J.C., Gullen E., Cheng Y.-C., and Zemlicka J. Bioorg. Med. Chem. 14 (2006) 1247
5. Hasobe M., Saneyoshi M., and Isono K. J. Antibiot. 38 (1985) 1581
6. Skipper H.E., Montgomery J.A., Thomson J.R., and Schabel Jr. F.M. Cancer Res. 19 (1959) 425
7. Cancer Res. 19 (1959) 287
8. Bowles W.A., Schneider F.H., Lewis L.R., and Robins R.K. J. Med. Chem. 6 (1963) 471
9. Kidder G.W., Dewey V.C., Parks R.E., and Woodside G.L. Cancer Res. 11 (1949) 204
10. Kern D.L., Hokanson G.C., French J.C., and Dalley N.K. J. Antibiot. 38 (1985) 572
11. Kitahara M., Ishii K., Kumada Y., Shiraishi T., Furuta T., Miwa T., Kawaharada H., and Watanabe K. J. Antibiot. 38 (1985) 972
12. Baker B.R., and Wood W.F. J. Med. Chem. 10 (1967) 1101
13. Baker B.R., Wood W.F., and Kozma J.A. J. Med. Chem. 11 (1968) 661
14. Kim S.-A., Marshall M.A., Melman N., Kim H.S., Mueller C.E., Linden J., and Jacobson K.A. J. Med. Chem. 45 (2002) 2131
15. Daly J.W., Padgett W.L., and Shamim M.T. J. Med. Chem. 29 (1986) 1305
16. Shimada J., Suzuki F., Nonaka H., and Ishii A. J. Med. Chem. 35 (1992) 924
17. Dooley M.J., and Quinn R.J. Bioorg. Med. Chem. Lett. 2 (1992) 1199
18. Miyamoto K., Takagi K., Sakai R., Wakusawa S., Koshiura R., Nadai M., Apichartpichean R., and Hasegawa T. J. Pharm. Pharmacol. 41 (1989) 844
19. Daly J.W., Padgett W., Shamim M.T., Butts-Lamb P., and Waters J. J. Med. Chem. 28 (1985) 487
20. Yoneda F., and Nagamatsu T. J. Chem. Soc., Perkin Trans. 1 (1976) 1547
21. Lister J.H. Heterocycles 6 (1977) 383
22. Hedayatullah M. J. Heterocycl. Chem. 19 (1982) 249
23. Bram G., Decodts G., Bensaid Y., Farnoux C.C., Galons H., and Miocque M. Synthesis 543 (1985)
24. Mueller C.E. Synth. Commun. 24 (1994) 1311
25. Lee B.-H., Shin J.-H., Jang T.-S., Park J.-S., and Kang S.-W. J. Korean Chem. Soc. 41 (1997) 357
26. Coulson C.J., Ford R.E., Lunt E., Marshall S., Pain D.L., Rogers I.H., and Wooldridge K.R.H. Eur. J. Med. Chem. 9 (1974) 313
27. Norris E.R., and Roush A. Arch. Biochem. 28 (1950) 465
28. Ellison R.E., and Burchenal J.H. Clin. Pharmacol. Therap. 1 (1960) 631
29. Whittington R.M., Rivers S.L., Doyle R.T., and Kodlin D. Cancer Chemother. Rept. 18 (1962) 73
30. Piro L.D., Carrera C.J., Beutler E., and Carson D.A. Blood 72 (1988) 1069
31. Parker W.B., Secrist III J.A., and Wand W.R. Curr. Opin. Invest. Drugs (Thomson Scientific) 5 (2004) 592
32. Kurtz J.-E., Andres E., Natarajan-Ame S., Noel E., and Dufour P. Eur. J. Internal Med. 14 (2003) 18
33. Nagamatsu T., Yamasaki H., Akiyama T., Hara S., Mori K., and Kusakabe H. Synthesis (1999) 655
34. Nagamatsu T., Yamasaki H., Fujita T., Endo K., and Machida H. J. Chem. Soc., Perkin Trans. 1 (1999) 3117
35. Nagamatsu T., and Fujita T. Chem. Commun. (1999) 1461
36. Nagamatsu T., Fujita T., and Endo K. J. Chem. Soc. Perkin Trans. 1 (2000) 33
37. Nübel G., and Pfleiderer W. Chem. Ber. 98 (1965) 1060
38. 3), 4.25 (3H, s, 2-NCH,), 11.47 (1H, s, NH).
39. Bozoova A., Rybar A., Alfoldi J., and Basnakova G. Coll. Czech. Chem. Commun. 57 (1992) 1314
40. -1 (CO)]: 3a: 1720, 1680; 13a: 1725, 1680; 13b: 1720, 1670; 13c: 1720, 1680; 13d: 1725, 1670; 14a: 1710; 14b: 1720; 14c: 1720; 14d: 1720; 14e: 1710.
41. mH), 7.23-7.28 (3H, m, Ph-o,pH).
42. 3), 126.02 (7a-C), 147.41(3a-C), 155.64 (7-C), 157.28 (5-C).
43. max/nm (log s) in EtOH]: 3a: 240 (4.06), 257 (4.08); 13a: 243 (4.18), 256 (4.21); 13b: 242 (4.20), 256 (4.22); 13c: 242 (4.21), 256 (4.23); 13d: 242 (4.12), 257 (4.17); 14a: 250 (4.18); 14b: 263 (4.36); 14c: 252 (4.26); 14d: 252 (4.27); 14e: 252 (4.35).