Synthesis, structural elucidation and DNA-dependant protein kinase and antiplatelet studies of 2-amino-[5, 6, 7, 8-mono and 7, 8-di-substituted]-1,3- benzoxazines

European Journal of Medicinal Chemistry

Volumn 45, Issue 11, 2010, Pages 4934-4946

  Ihmaid, Saleh ^a   Al Rawi, Jasim ^a   Bradley, Christopher ^a  

^a LA TROBE UNIVERSITY   (Australia)

Author keywords

2 Amino O subst 1,3 benzoxazines; Antiplatelet; DNA dependant protein kinase

Indexed keywords

2 MORPHOLIN 4 YL 7 (PYRIDIN 4 YLMETHOXY) 4H 1,3 BENZOXAZIN 4 ONE; 5 (2 CHLOROETHOXY) 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 5 HYDROXY 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 5 HYDROXY 2 THIOXO 2,3 DIHYDRO 4H 1,3 BENZOXAZIN 4 ONE; 5 METHOXY 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 5 METHOXY 2 THIOXO 2,3 DIHYDRO 4H 1,3 BENZOXAZIN 4 ONE; 6 (2 BROMOETHOXY) 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 6 ETHOXY 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 6 HYDROXY 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 6 HYDROXY 2 THIOXO 2,3 DIHYDRO 4H 1,3 BENZOXAZIN 4 ONE; 6 METHOXY 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 6 METHOXY 2 THIOXO 2,3 DIHYDRO 4H 1,3 BENZOXAZIN 4 ONE; 6,8 DIBROMO 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 7 (2 BROMOETHOXY) 8 METHYL 2 THIOMORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 7 ETHOXY 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 7 ETHOXY 2 THIOXO 2,3 DIHYDRO 4H 1,3 BENZOXAZIN 4 ONE; 7 FLUORO 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 7 FLUORO 2 THIOXO 2,3 DIHYDRO 4H 1,3 BENZOXAZIN 4 ONE; 7 HYDROXY 8 METHYL 2 PIPRDINE 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 7 HYDROXY 8 METHYL 2 THIO MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 8 (2 BROMOETHOXY) 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 8 (2 CHLOROETHOXY) 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 8 HYDROXY 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 8 HYDROXY 2 THIOXO 2,3 DIHYDRO 4H 1,3 BENZOXAZIN 4 ONE; 8 ISOPROPYL 2 MORPHOLIN 4 YL 4H 1,3 BENZOXAZIN 4 ONE; 8 ISOPROPYL 2 THIOXO 2,3 DIHYDRO 4H 1,3 BENZOXAZIN 4 ONE; 8 METHYL 2 MORPHOLIN 4 YL 7 (PYRIDIN 3 YLMETHOXY) 4H 1,3 BENZOXAZIN 4 ONE; ANTITHROMBOCYTIC AGENT; DNA DEPENDENT PROTEIN KINASE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; THROMBOCYTE AGGREGATION;

BENZOXAZINES; DNA-ACTIVATED PROTEIN KINASE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PLATELET AGGREGATION INHIBITORS; SPECTROPHOTOMETRY, INFRARED;

EID: 77957832718     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.07.066     Document Type: Article

References (26)

1. M. Frazzetto, C. Suphioglu, J. Zhu, O. Schmidt-Kittler, I.G. Jennings, and S.L. Cranmer J. Biochem. 414 3 2008 383 390
2. B. Vanhaesebroeck, S.J. Leevers, K. Ahmadi, J. Timms, R. Katso, and P.C. Driscoll Annu. Rev. Biochem. 70 2001 535 602
3. Y. Samuels, and V.E. Velculescu Cell Cycle 3 10 2004 1221 1224
4. P. Workman J. Biochem. Soc. Trans. 32 2004 393 396
5. L. Stephens, R. Williams, and P. Hawkins Curr. Opin. Pharmacol. 5 4 2005 357 365
6. S.P. Jackson, S.M. Schoenwaelder, I. Goncalves, W.S. Nesbitt, C.L. Yap, and C.E. Wright Nat. Med. 11 5 2005 507 514
7. E. Hirsch, V.L. Katanaev, C. Garlanda, O. Azzolino, L. Pirola, and L. Silengo Science 287 2000 1049 1053
8. M. Camps, T. Ruckle, H. Ji, V. Ardissone, F. Rintelen, and J. Shaw Nat. Med. 11 9 2005 936 943
9. G.C.M. Smith, and S.P. Jackson Genes Dev. 13 8 1999 916 934
10. S.G. Chaney, and A.J. Sancar J. Natl. Cancer Inst. 88 19 1996 1346 1360
11. R. Griffin, G. Fontana, B. Golding, S. Guiard, I. Hardcastle, and J. Leahy J. Med. Chem. 48 2 2005 569 585
12. H.C. Diener, L. Cunha, C. Forbes, J. Sivenius, P. Smets, and A. lowenthal J. NeuroScience. 143 1-2 1996 1 13
13. B. Abbott, P. Thompson, and E. Philip Bioorg. Med. Chem. 14 11 2004 2847 2851
14. C.J. Vlahos, W.F. Matter, K.Y. Hui, and R.F. Brown J. Biol. Chem. 269 7 1994 5241 5248
15. I. Hardcastle, X. Cockcroft, N. Curtin, M. El-Murr, J. Leahy, and M. Stockley J. Med. Chem. 48 24 2005 7829 7846
16. J. Leahy, B. Golding, R. Griffin, I. Hardcastle, C. Richardson, and L. Rigoreau Bioorg. Med. Chem. 14 24 2004 6083 6087
17. J. Morris, D.G. Wishka, A.H. Lin, W.R. Humphrey, A.L. Wiltse, and R.B. Gammill J. Med. Chem. 36 14 1993 2026 2032
18. K.M. Pritchard, J.M. Al-Rawi, and C. Bradley Eur. J. Med. Chem. 42 2007 1200 1210
19. K.M. Pritchard, J.M. Al-Rawi, and A.B. Hughes Synth. Commun. 35 2005 1601 1611
20. N. Teruhisa, Fujisawa-shi, K. Keisukeetal, Japan patent 1,542,484, 1968.
21. R.B. Gammill, T.M. Judge, J. Morris, US Patent 89/05526, 1990.
22. U.R. Kuppusamy, and N.P. Das Biochem. Pharmocol. 44 7 1992 1307 1315
23. L.C. Foukas, N. Daniele, C. Ktori, K.E. Anderson, J. Jensen, and P.R. Shepherd J. Biol. Chem. 277 40 2002 37124 37130
24. D. Kong, S.I. Yaguchi, and T. Yamori Biol. Pharm. Bull. 32 2 2009 297 300
25. C.M. Lee, C.B. Fuhrman, V. Planelles, R. Morgan, D.K. Gaffney, and A.P. Soisson Clin. Cancer Res. 12 1 2006 250 256
26. T. Noguchi Fuj-shi, K. Komoto, Hira-tsuka-shi, et al. US patent 3595959, 1971.