Neurotransmitter amino acid-oxobenzo[f]benzopyran conjugates: synthesis and photorelease studies

Tetrahedron

Volumn 64, Issue 49, 2008, Pages 11175-11179

  Fernandes, Maria J G ^a   Gonçalves, M Sameiro T ^a   Costa, Susana P G ^a  

^a UNIVERSITY OF MINHO   (Portugal)

Author keywords

Amino acids; Benzocoumarin; Neurotransmitters; Oxobenzobenzopyran; Photolysis

Indexed keywords

1 CHLOROMETHYL 9 METHOXY 3 OXO 3H BENZO[F]BENZOPYRAN; BENZOPYRAN DERIVATIVE; BETA ALANINE; DOPA; GLUTAMIC ACID; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; IRRADIATION; NEUROTRANSMISSION; PHOTOCHEMISTRY; PHOTOLYSIS; PRIORITY JOURNAL; SYNTHESIS;

EID: 54549092397     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.050     Document Type: Article

References (37)

1. Bochet C.G. J. Chem. Soc., Perkin Trans. 1 (2002) 125
2. Pelliccioli A.P., and Wirz J. Photochem. Photobiol. Sci. 1 (2002) 441
3. Greene T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. (1999), Wiley, New York, NY
4. Kocienski P.J. Protecting Groups (2000), Georg Thieme, New York, NY
5. Goeldner M., and Givens R.S. Dynamic Studies in Biology: Phototriggers, Photoswitches and Caged Biomolecules (2005), Wiley-VCH, Weinheim
6. Mayer G., and Heckel A. Angew. Chem., Int. Ed. 45 (2006) 4900
7. Loudwig S., and Goeldner M. Tetrahedron Lett. 42 (2001) 7957
8. Peng L., Wirz J., and Goeldner M. Tetrahedron Lett. 38 (1997) 2961
9. Dinkel C., Wichmann O., and Schultz C. Tetrahedron Lett. 44 (2003) 1153
10. Dinkel C., and Schultz C. Tetrahedron Lett. 44 (2003) 1157
11. Li W.-h., Llopis J., Whitney M., Zlokarnik G., and Tsien R.Y. Nature 392 (1998) 936
12. Wang P., Hu H., and Wang Y. Org. Lett. 9 (2007) 1533
13. Yu J.-Y., Tang W.-J., Wang H.-B., and Song Q.-H. J. Photochem. Photobiol., A 185 (2007) 101
14. Kantevari S., Narasimhaji C.V., and Mereyala H.B. Tetrahedron 61 (2005) 5849
15. Bochet C.G. Tetrahedron Lett. 41 (2000) 6341
16. Schaper K., Mobarekah S.A.M., and Grewer C. Eur. J. Org. Chem. (2002) 1037
17. Banerjee A., Grewer C., Ramakrishnan L., Jäger J., Gameiro A., Breitinger H.-G.A., Gee K.R., Carpenter B.K., and Hess G.P. J. Org. Chem. 68 (2003) 8361
18. Grewer C., Jäger J., Carpenter B.K., and Hess G.P. Biochemistry 39 (2000) 2063
19. Singh A.K., and Khade P.K. Tetrahedron 61 (2005) 10007
20. Givens R.S., Weber J.F.W., Conrad P.G., Orosz G., Donahue S.L., and Thayer S.A. J. Am. Chem. Soc. 122 (2000) 2687
21. Ma C., Steinmetz M.G., Kopatz E.J., and Rathore R. J. Org. Chem. 70 (2005) 4431
22. Ashraf M.A., Russell A.G., Wharton C.W., and Snaith J.S. Tetrahedron 63 (2007) 586
23. Papageorgiou G., Ogden D.C., Barth A., and Corrie J.E.T. J. Am. Chem. Soc. 121 (1999) 6503
24. Shembekar V.R., Chen Y., Carpenter B.K., and Hess G.P. Biochemistry 44 (2005) 7107
25. Hagen V., Dekowski B., Kotzur N., Lechler R., Wiesner B., Briand B., and Beyermann M. Chem.-Eur. J. 14 (2008) 1621
26. Piloto A.M., Rovira D., Costa S.P.G., and Gonçalves M.S.T. Tetrahedron 62 (2006) 11955
27. Fonseca A.S.C., Gonçalves M.S.T., and Costa S.P.G. Tetrahedron 63 (2007) 1353
28. Hill C.A., Harris R.C., Kim H.J., Harris B.D., Sale C., Boobis L.H., Kim C.K., and Wise J.A. Amino Acids 32 (2007) 225
29. Misu Y., Goshima Y., and Miyamae T. Trends Pharmacol. Sci. 23 (2002) 262
30. Kreibich T.A., Chalasani S.H., and Raper J.A. J. Neurosci. 24 (2004) 7085
31. Piloto A.M., Costa S.P.G., and Gonçalves M.S.T. Tetrahedron Lett. 46 (2005) 4757
32. Piloto A.M., Fonseca A.S.C., Costa S.P.G., and Gonçalves M.S.T. Tetrahedron 62 (2006) 9258
33. Fernandes M.J.G., Gonçalves M.S.T., and Costa S.P.G. Tetrahedron 64 (2008) 3032
34. Tjoeng F.S., and Heavner G.A. Synthesis (1981) 897
35. Morris J.V., Mahaney M.A., and Huber J.R. J. Phys. Chem. 80 (1976) 969
36. Muller C., Even P., Viriot M.-L., and Carré M.-C. Helv. Chim. Acta 84 (2001) 3735
37. Fernandes M.J.G., Gonçalves M.S.T., and Costa S.P.G. Tetrahedron 63 (2007) 10133