Abstract:
This paper reports a synthesis of novel diheteroarylethenes functionalized for coupling to biomolecules starting from indole derivatives. The strategy is based on the derivatization at the N-atom in the indole substructure. TBDMS protection proved to be superior over BOC protection schemes, leading to higher yields in the overall synthesis. The suitability of the new derivatives as acceptors for pcFRET was calculated for selected donors.
Referencias:
- Hirshberg, (1950) Compt. Rend., 231, p. 903
- Irie, M., (2000) Chem. Rev., 100, p. 1685
- Yagi, K., Irie, M., (2003) Bull. Chem. Soc. Jpn., 76, p. 1625
- Giordano, L., Jovin, T.M., Irie, M., Jares-Erijman, E.A., (2002) J. Am. Chem. Soc., 124, p. 7481
- Jares-Erijman, E.A., Jovin, T.M., (2003) Nat. Biotechnol., 21, p. 1387
- Hanazawa, M., Sumiya, R., Horikawa, Y., Irie, M., (1992) J. Chem. Soc., Chem. Commun., p. 206
- Greene, T.W., Wuts, P.G.M., (1999) Protective Goups in Organic Synthesis, , Wiley-Interscience: New York., 3rd Edn
- Dhanak, D., Reese, C.B., (1986) J. Chem. Soc., Perkin Trans. 1, p. 2181
- Witulski, B., Buschmann, N., Bergstrasser, U., (2000) Tetrahedron, 56, p. 8473
- Bodwell, G.J., Li, J., (2002) Org. Lett., 4, p. 127
- Amat, M., Hadida, S., Sathyanarayana, S., Bosch, J., (1994) J. Org. Chem., 59, p. 10
- Cross, P.E., Dickinson, R.P., Parry, M.J., Randall, M.J., (1986) J. Med. Chem., 29, p. 1637
- Bell, M.R., Dambra, T.E., Kumar, V., Eissenstat, M.A., Herrmann, J.L., Wetzel, J.R., Rosi, D., Ward, S.J., (1991) J. Med. Chem., 34, p. 1099
- Frigoli, M., Mehl, G.H., (2004) Chem.- Eur. J., 10, p. 5243
- Nakashima, H., Irie, M., (1998) Polymer J., 30, p. 985
- Orazi, O., Corral, R.A., Bertorello, H.E., (1965) J. Org. Chem., 30, p. 1101
Citas:
---------- APA ----------
Giordano, L., Vermeij, R.J. & Jares-Erijman, E.A.
(2006)
. Synthesis of indole-containing diheteroarylethenes. New probes for photochromic FRET (pcFRET). Arkivoc, 2005(12), 268-281.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p268_Giordano [ ]
---------- CHICAGO ----------
Giordano, L., Vermeij, R.J., Jares-Erijman, E.A.
"Synthesis of indole-containing diheteroarylethenes. New probes for photochromic FRET (pcFRET)"
. Arkivoc 2005, no. 12
(2006) : 268-281.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p268_Giordano [ ]
---------- MLA ----------
Giordano, L., Vermeij, R.J., Jares-Erijman, E.A.
"Synthesis of indole-containing diheteroarylethenes. New probes for photochromic FRET (pcFRET)"
. Arkivoc, vol. 2005, no. 12, 2006, pp. 268-281.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p268_Giordano [ ]
---------- VANCOUVER ----------
Giordano, L., Vermeij, R.J., Jares-Erijman, E.A. Synthesis of indole-containing diheteroarylethenes. New probes for photochromic FRET (pcFRET). Arkivoc. 2006;2005(12):268-281.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p268_Giordano [ ]