5528
A. Staszewska et al. / Tetrahedron Letters 46 (2005) 5525–5528
9. Bra¨se, S.;Gil, C.;Knepper, K. Bioorg. Med. Chem. 2002,
10, 2415–2437.
References and notes
10. Wu, Z.;Ede, N. J. Tetrahedron Lett. 2001, 42, 8115–8118.
11. Fields, G. B. In Methods in Enzymology: Solid-Phase
Peptide Synthesis;Academic Press: New York, 1997;
Vol. 289, pp 63–64.
1. (a) Wang, L.;Schultz, P. G.. Chem. Commun. 2002, 1–11;
(b) Parsons, A. F. Tetrahedron 1996, 52, 4149–4174;(c)
Duthaler, R. O. Tetrahedron 1994, 50, 1539–1650;(d)
Anderson, R. D.;Zhou, J.;Hecht, S. M. J. Am. Chem.
Soc. 2002, 124, 9674–9675;(e) Scott, W. L.;O ÕDonnell, M.
J.;Delgado, F.;Alsina, J. J. Org. Chem. 2002, 67, 2960–
2969;(f) Adlington, R. M.;Baldwin, J. E.;Catterick, D.;
Pritchard, G. J. J. Chem. Soc., Perkin Trans. 1 1999, 855–
866, and references cited thererin;(g) Adlington, R. M.;
12. Selected analytical data: Compound 4a: HPLC:
m/z 427 ([MH]+); 1H NMR
tR = 34.0 min;ESI-MS
(DMSO-d6, 500 MHz): d 3.19 (m, 1H), 3.40 (m, 1H),
3.89 (m, 2H), 4.17 (m, 1H), 7.38 (m, 6H), 7.46 (m, 4H),
7.82 (d, 1H, J = 8.6 Hz), 8.08 (s, 1H), 8.12 (d, 1H,
J = 8.5 Hz), 8.81 (m, 1H).
Compound 4b: HPLC tR = 21.4 min;ESI-MS m/z 429
([MH]+); 1H NMR (DMSO-d6, 500 MHz): d 3.27 (m, 1H),
3.45 (m, 1H), 3.90 (m, 2H), 4.29 (m, 1H), 7.36 (m, 2H),
7.89 (d, 1H, J = 8.6 Hz), 7.97 (m, 4H), 8.14 (s, 1H), 8.18
(d, 1H, J = 8.5 Hz), 8.94 (m, 1H).
Compound 4c: HPLC tR = 34.8 min;ESI-MS m/z 487
([MH]+); 1H NMR (DMSO-d6, 500 MHz): d 3.21 (m, 1H),
3.40 (m, 1H), 3.78 (s, 6H) 3.90 (m, 2H), 4.25 (m, 1H), 6.94
(m, 4H), 7.43 (m, 4H), 7.75 (d, 1H, J = 8.6 Hz), 8.02 (s,
1H), 8.05 (d, 1H, J = 8.5 Hz), 8.91 (m, 1H).
Baldwin, J. E.;Catterick, D.;Pritchard, G. J.
Commun. 1997, 1757–1758.
Chem.
2. (a) Dougherty, D. A. Curr. Opin. Chem. Biol. 2000, 4, 645–
652;For reviews, see: (b) Cornish, V. W.;Mendel, D.;
Schultz, P. G. Angew. Chem., Int. Ed. Engl. 1995, 34, 621–
633;(c) Noren, C. J.;Anthony-Cahill, S. J.;Griffith, M.
C.;Schultz, P. G. Science 1989, 244, 182–188;(d) Voyer,
N.;Larnothe, J. Tetrahedron 1995, 51, 9241–9284.
3. (a) Jaso, A.;Zarranz, B.;Aldana, I.;Monge, A. J. Med.
Chem. 2005, 48, 2019–2025;(b) Gali-Muhtasib, H. U.;
Diab-Assaf, M.;Haddadin, M. J.
Cancer Chemoth.
Compound 4d: HPLC tR = 19.3 min;ESI-MS m/z 303
Pharm. 2005, 55, 369–378;(c) Perez-Melero, C.;Maya,
A. B. S.;del Rey, B.;Palaez, R.;Caballero, E.;Medarde,
M. Bioorg. Med. Chem. Lett. 2004, 14, 3771–3774;(d)
Aguirre, G.;Cerecetto, H.;Di Maio, R.;Gonzales, M.;
Alfaro, M. E. M. A.;Jaso, A.;Zarranz, B.;Ortega, M. A.;
Aldana, I.;Monge-Vega, A. Bioorg. Med. Chem. Lett.
2004, 14, 3835–3839;(e) Toshima, K.;Ozawa, T.;Kimura,
T.;Matsumara, S. Bioorg. Med. Chem. Lett. 2004, 14,
2777–2779.
1
([MH]+); H NMR (DMSO-d6, 500 MHz): d 2.66 (s, 6H)
3.15 (m, 1H), 3.35 (m, 1H), 3.88 (m, 2H), 4.20 (m, 1H),
7.65 (d, 1H, J = 8.6 Hz), 7.87 (s,1H), 7.91 (d, 1H,
J = 8.5 Hz), 8.88 (m, 1H).
Compound 4e: HPLC tR = 28 min;ESI-MS m/z 407
([MH]+).
Compound 4f: HPLC tR = 41.0 min;ESI-MS m/z 425
([MH]+); 1H NMR (DMSO-d6, 500 MHz): d 3.30 (m, 1H),
3.48 (m, 1H), 3.92 (m, 2H), 4.32 (m, 1H), 7.82 (m, 2H),
7.89 (m, 2H), 7.92 (d, 1H, J = 8.8 Hz), 8.26 (s, 1H), 8.29
(m, 1H), 8.80 (d, 2H, J = 8.0 Hz), 9.26 (m, 2H) 8.98 (m,
1H).
4. (a) Santra, B. K.;Reddy, P. A. N.;Neelakanta, G.;
Mahadevan, S.;Nethaji, M.;Chakravarty, A. R. J. Inorg.
Biochem. 2002, 89, 191–196;(b) Thomas, A. M.;Nethaji,
M.;Mahadevan, S.;Chakravarty, A. R. J. Inorg. Biochem.
2003, 94, 171–178.
5. Wu, J.-Z.;Xu, Z.-G.;Li, Y.;Zhang, W.-G.;Zeng, H.-P.;
Xu, X.;Zhou, Z.-Z. J. Chem. Crystallogr. 2002, 32, 75–80.
6. Zhao, Z.;Wisnoski, D. D.;Wolkenberg, S. E.;Leister, W.
H.;Wang, Y.;Lindsley, C. W. Tetrahedron Lett. 2004, 45,
4873–4876.
7. (a) Wasserman, H. H.;Long, Y. O.;Parr, J. Tetrahedron
Lett. 2003, 44, 361–363;(b) Huang, X.;Long, E. C. H.
Bioorg. Med. Chem. Lett. 1995, 5, 1937–1940;(c) Kotha,
S.;Brahmachary, E.;Kuki, A.;Lang, K.;Anglos, D.;
Singaram, B.;Chrisman, W. Tetrahedron Lett. 1997, 38,
9031–9034;(d) El-Faham, A.;El Massry, A. M.;Amer,
A.;Gohar, Y. M. Lett. Pept. Sci. 2002, 9, 49–54.
8. Brown, A. R.;Hermkens, P. H. H.;Ottenheijm, H. C. J.;
Rees, D. C. Synlett 1998, 817–827.
Compound 4g: HPLC tR = 21.0;ESI-MS
m/z 427
([MH]+);HPLC: C18 column Vydac: solv. A water + 0.1%
TFA, solv. B acetonitrile + 0.1% TFA;gradient 0–100% B
in A over 60 min.
13. Crystallographic data for the structure in this paper have
been deposited with the Cambridge Crystallographic Data
Centre as supplementary data no. CCDC 269209. Copies
of the data can be obtained free of charge, on application
to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK
14. Atherton, E.;Scheppart, R. C. Solid Phase Peptide
Synthesis;IRL Press: Oxford, New York, Tokyo, 1989,
p 12.
15. Paw, W.;Eisenberg, R. Inorg. Chem. 1997, 36, 2287–2293.