Synthesis of the new ring system 2-oxo-[1,4]oxazino[3,2-e]indole, heteroanalogue of Angelicin

Tetrahedron Letters

Volumn 50, Issue 28, 2009, Pages 4182-4184

  Barraja, Paola ^a   Diana, Patrizia ^a   Montalbano, Alessandra ^a   Martorana, Annamaria ^a   Carbone, Anna ^a   Cirrincione, Girolamo ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

1,4 Benzoxazines; 1,4 Oxazinoindoles; 4 Amino 5 hydroxy indoles; Angelicin heteroanalogue

Indexed keywords

ANGELICIN; INDOLE DERIVATIVE;

ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; ULTRAVIOLET A RADIATION;

EID: 66149115993     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.007     Document Type: Article

References (20)

1. Dall'Acqua F., and Viola G. In: Coohil T.P., and Valenzeno D.P. (Eds). Photobiology for the 21th century (2001), Valdenmar, Overland Park, KS 325
2. Jakobs A.E., and Piette J. J. Photochem. Photobiol. B. 22 (1994) 9-15
3. Jakobs A.E., and Piette J. J. Med. Chem. 38 (1995) 869-874
4. Rodighiero P., Guiotto A., Chilin A., Bordin F., Baccichetti F., Carlassare F., Vedaldi D., Caffieri S., Pozzan A., and Dall'Acqua F. J. Med. Chem. 39 (1996) 1293-1302
5. Barraja P., Diana P., Lauria A., Montalbano A., Almerico A.M., Dattolo G., Cirrincione G., Viola G., and Dall'Acqua F. Bioorg. Med. Chem. Lett. 13 (2003) 2809-2811
6. Barraja P., Diana P., Montalbano A., Dattolo G., Cirrincione G., Viola G., Vedaldi D., and Dall'Acqua F. Bioorg. Med. Chem. 14 (2006) 8712-8728
7. Barraja P., Sciabica L., Diana P., Lauria A., Montalbano A., Almerico A.M., Dattolo G., Cirrincione G., Disarò S., Basso G., Viola G., and Dall'Acqua F. Bioorg. Med. Chem. Lett. 15 (2005) 2291-2294
8. Barraja P., Diana P., Montalbano A., Carbone A., Cirrincione G., Viola G., Salvador A., Vedaldi D., and Dall'Acqua F. Bioorg. Med. Chem. 16 (2008) 9668-9683
9. Thuillier G., Laforest J., Bessin P., Bonnet J., and Thuillier J. Eur. J. Med. Chem. 10 (1975) 37-42
10. Reusser F. J. Antibiot. 32 (1979) 1186-1192
11. Reusser F. Biochemistry 12 (1973) 1136-1142
12. Turk C.F., Krapcho J., Michel I.M., and Weinryb I. J. Med. Chem 20 (1977) 729-732
13. Kimura K., Usui Y., Hattori T., Yamakawa N., Goto H., Usui M., Okada S., Shirato K., and Tomoda A. Oncol. Rep. 19 (2008) 3-10
14. Ishihara M., Kawase M., Westman G., Samuelsson K., Motohashi N., and Sakagami H. Anticancer Res. 27 (2007) 4053-4057
15. Mas, J. -M.; Rochin, C. PCT Int. Appl. WO 9724316, 1997; Chem. Abstr. 1997, 127, 108760.
16. Ray, P. C.; Medikonduri, S.; Ramanjaneyulu, G. S. PCT Int. Appl. WO 083320, 2007; Chem. Abstr. 2007, 147, 21894.
17. Rodighiero P., Chilin A., Pastorini G., and Guiotto A. J. Heterocyc. Chem. 24 (1987) 1041-1043
18. Allen G.R., Pidacks C., and Weiss M.J. J. Am. Chem. Soc. 88 (1966) 2536-2544
19. Everett S.A., Naylor M.A., Barraja P., Swann E., Patel K.B., Stratford M.R.L., Hudnott A.R., Vojnovic B., Locke R.J., Wardman P., and Moody C.J. J. Chem. Soc., Perkin Trans. 2 (2001) 843-860
20. 2), 4.83-4.89 (1H, m, H-3), 6.86 (1H, d, J = 8.8 Hz, H-6), 7.11 (1H, d, J = 8.8 Hz, H-5), 11.60 (1H, s, NH)