Studies on the acylation of 4-(2-aminoethylthio)-7-nitrobenzofurazan: The role of bases in promoting the formation of fluorescent S-acyl derivatives through S-N Smiles rearrangement

Tetrahedron Letters

Volumn 53, Issue 37, 2012, Pages 5008-5011

  Castagnolo, Daniele ^a   Pagano, Mafalda ^a   Bernardini, Martina ^a   Botta, Maurizio ^a,b  

^a UNIVERSITY OF SIENA   (Italy)

^b Temple University   (United States)

Author keywords

Benzofurazan; Cysteamine; Fluorescent probe; S N acylation; Smiles rearrangement

Indexed keywords

4 (2 AMINOETHYLTHIO) 7 NITROBENZOFURAZAN; BASE; BENZOFURAZAN DERIVATIVE; NITROGEN; SULFUR; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; ISOMER; REACTION ANALYSIS; SMILES REARRANGEMENT;

EID: 84865025391     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.07.033     Document Type: Article

References (26)

1. M. Ioannis, P. Takakis, and M. Hadjimihalakis J. Heterocycl. Chem. 27 1990 177 181
2. L.D. Lavis, and R.T. Raines ACS Chem. Biol. 3 2008 142 155
3. M. Bem, F. Badea, C. Draghici, M.T. Caproiu, M. Vasilescu, M. Voicescu, A. Beteringhe, A. Caragheorgheopol, M. Maganu, T. Constantinescu, and A.T. Balaban ARKIVOC 2007 87 104
4. Y. Numasawa, K. Okabe, S. Uchiyama, T. Santa, and K. Imai Dyes Pigm. 67 2005 189 195
5. G. Allen, and G. Lowe Biochem. J. 133 1973 679 686
6. S. Uchiyama, T. Santa, T. Fukushima, H. Homma, and K. Imai J. Chem. Soc., Perkin Trans. 2 1998 2165
7. S. Uchiyama, K. Takehira, S. Kohtani, K. Imai, R. Nakagaki, S. Tobita, and T. Santa Org. Biomol. Chem. 1 2003 1067 1072
8. S. Uchiyama, T. Santa, and K. Imai J. Chem. Soc., Perkin Trans. 2 1999 2525 2532
9. F. Terrier, and H. Feuer In Nucleophilic Aromatic Displacement 1991 VCH New York
10. E. Buncel, M.R. Crampton, M.J. Strauss, and F. Terrier In Electron-Deficient Aromatic and Heteroaromatic Base Interactions 1984 Elsevier Amsterdam 166 296
11. F. Terrier Chem. Rev. 82 1982 77
12. E. Buncel, J.M. Dust, and F. Terrier Chem. Rev. 95 1995 2261
13. M. Shipton, T. Stuchjbury, and K. Brocklehurst Biochem. J. 159 1976 235 244
14. S.T. Ferguson, W.J. Lloyd, and G.K. Radda Biochem. J. 159 1976 347 353
15. S. Uchiyama, T. Santa, N. Okiyama, T. Fukushima, and K. Imai Biomed. Chromatogr. 15 2001 295 318
16. P.B. Ghosh, and M.W. Whitehouse J. Med. Chem. 11 1968 1305 1311
17. G.G. Borisenko, A.A. Kapralov, V.A. Tyurin, A. Maeda, D.A. Stoyanovsky, and V.E. Kagan Biochemistry 47 2008 13699 13710
18. R.C. Fu, X.F. Liu, and S. Chen J. Neurochem. 55 1990 813 818
19. D. Castagnolo, M. Pagano, M. Bernardini, and M. Botta Synlett 2009 2093 2096
20. M. Radi, L. Contemori, D. Castagnolo, R. Spinosa, J.A. Esté, S. Massa, and M. Botta Org. Lett. 9 2007 3157 3160
21. M. Radi, G. Maga, M. Alongi, L. Angeli, A. Samuele, S. Zanoli, L. Bellucci, A. Tafi, G. Casaluce, G. Giorgi, M. Armand-Ugon, E. Gonzalez, J.A. Esté, M. Baltzinger, G. Bec, P. Dumas, E. Ennifar, and M. Botta J. Med. Chem. 52 2009 840 851
22. G. Ah-Kow, and F. Terrier J. Org. Chem. 43 1978 3578 3584
23. R.O. Al-Kaysi, I. Gallardo, and G. Guirado Molecules 13 2008 1282 1302
24. L.A. Warren, and S.J. Smiles Chem. Soc. 1931 914 922
25. T. Wieland, and E. Bokelmann Justus Liebigs. Ann. Chem. 576 1952 20 34
26. H.P. Burchfield Nature 181 1958 49 50