Synthesis Of Novel Indole-Based Ring Systems By Acid-Catalyzed Condensation From A-Amino Aldehydes And L-Trp-Ome(262 views) Gomez-monterrey IM, Campiglia P, Bertamino A, Aquino C, Mazzoni O, Diurno MV, Iacovino R, Saviano M, Sala M, Novellino E, Grieco P
European Journal Of Organic Chemistry (ISSN: 1434-193x), 2008; 11: 1983-1992.
Department of Pharmaceutical and Toxicological Chemistry, University of Naples Federico II, 80131 Naples, Italy
Department of Environmental Sciences, Second University of Naples, 81100 Caserta, Italy
Institute of Biostructures and Bioimaging, CNR, 80134 Naples, Italy
References: Gordon, E.M., (1998) Combinatorial Chemistry and Molecular Diversity in Drug Discovery, , Eds, E. M. Gordon, J. F. Kerwin Jr, Wiley-Liss, New Yor
Pavia, M.R., Sawyer, T.K., Moose, W.H., (1993) Bioorg. Med. Chem. Lett, 3, pp. 387-396
Sawyer, T.K., (1997) Structure Based Drug Design: Disease, Targets, Techniques and Development, p. 559. , Ed, P. Veerapandian, Marcel Dekker, New York
Grieco, P., Campiglia, P., Gomez-Monterrey, I.M., Novellino, E., (2002) Tetrahedron Lett, 43, pp. 6297-6299
Grieco, P., Giusti, L., Carotenuto, A., Campiglia, P., Calderone, V., Lama, T., Gomez-Monterrey, I.M., Novellino, E., (2005) J. Med. Chem, 48, pp. 3153-3163
Campiglia, P., Carotenuto, A., Lama, T., Diurno, M.V., Bertamino, A., Mazzoni, O., Sala, M., Grieco, P., (2006) Lett. Org. Chem, 3, pp. 539-545
De la Figuera, N., Alkorta, I., Garcia-Lopez, M.T., Herranz, R., Gonzalez-Muniz, R., (1995) Tetrahedron, 51, pp. 7841-7856
Li, X., Zhang, L., Zhang, W., Hall, S.E., Tam, J.P., (2000) Org. Lett, 2, pp. 3075-3078
Lubell, W.D., Rapoport, H., (1987) J. Am. Chem. Soc, 109, pp. 236-239
Ungemach, F., Soerens, D., Weber, R., Di Pierro, M., Campos, O., Mokry, P., Cook, J.M., Silverton, J.V., (1980) J. Am. Chem. Soc, 102, pp. 6976-6984
Derivatives 10-13 exist as mixtures of two rotamers about the urethane linkageCrystallographic data for 17a: C26H31N 3O4·CH2Cl2, M, 533.47, orthorhombic, space group P21212 1, a, 11.23(2, b, 14.720(10, c, 17.260(10) Å, V, 2853(6) Å3, Z, 4, d, 1.244 g/cm 3, crystal dimensions 0.30x0.30x0.25 mm were used for measurements on a Nonius-Mach3 instrument with a graphite monochromator (ω-2θ scans, θmax, 25.0°, Mo-Kα radiation. The total number of reflections measured was 2829, of which 2829 were unique and 1621 observed, I >
2σ(I, Final indices: Rf, 0.0699, Rw, 0.1644 for observed reflections, and R1, 0.1407, wR2, 0.2111 for all reflections 2829, The crystal structure of 17a was solved by direct methods usinTietze, L.F., (1996) Chem. Rev, 96, pp. 115-136
Gonzalez-Vera, J.A., Garcia-Lopez, M.T., Herranz, R., (2004) Org. Lett, 6, pp. 2641-2644. , for an example of this type of reaction on a triptophan-derived amino nitrile, see
Cox, E.D., Cook, J.M., (1995) Chem. Rev, 95, pp. 1797-1842. , and references cited therein
Bailey, P.D., Hollinshead, S.P., McLay, N.R., Morgan, K., Palmer, S.J., Prince, S.N., Reynolds, C.D., Wood, S.D., (1993) J. Chem. Soc., Perkin Trans. 1, pp. 431-439
Liu, J.-J., Hino, T., Tsuruoka, A., Harada, N., Nakagawa, M., (2000) J. Chem. Soc., Perkin Trans. 1, 20, pp. 3487-3494
Orain, D., Canova, R., Dattilo, M., Kloppner, E., Denay, R., Koch, G., Giger, R., (2002) Synlett, 9, pp. 1443-1446
Orain, D., Koch, G., Giger, R., (2003) Chimia, 57, pp. 255-261
Lee and Park recently reported the formation of this type of tetracyclic indole system via sequential cyclic iminium formation and a Pictet-Spengler cyclization reaction under acid conditions: S. C. Lee, B. J. Park, J. Comput. Chem. 2006, 8, 50-57UR - http://www.scopus.com/inward/record.url?eid=2-s2.0-53749102866&partnerID=40&md5=2bfdae6b9c4af6fdd2509c34ef7c5294
Gordon, E. M., (1998) Combinatorial Chemistry and Molecular Diversity in Drug Discovery, , Eds, E. M. Gordon, J. F. Kerwin Jr, Wiley-Liss, New Yor
Pavia, M. R., Sawyer, T. K., Moose, W. H., (1993) Bioorg. Med. Chem. Lett, 3, pp. 387-396
Sawyer, T. K., (1997) Structure Based Drug Design: Disease, Targets, Techniques and Development, p. 559. , Ed, P. Veerapandian, Marcel Dekker, New York
Lubell, W. D., Rapoport, H., (1987) J. Am. Chem. Soc, 109, pp. 236-239
Gonzalez-Vera, J. A., Garcia-Lopez, M. T., Herranz, R., (2004) Org. Lett, 6, pp. 2641-2644. , for an example of this type of reaction on a triptophan-derived amino nitrile, see
Cox, E. D., Cook, J. M., (1995) Chem. Rev, 95, pp. 1797-1842. , and references cited therein
Bailey, P. D., Hollinshead, S. P., McLay, N. R., Morgan, K., Palmer, S. J., Prince, S. N., Reynolds, C. D., Wood, S. D., (1993) J. Chem. Soc., Perkin Trans. 1, pp. 431-439
Cox, E. D., Hamaker, L. K., Li, J., Yu, P., Czerwinski, K. M., Deng, L., Bennett, D. W., Cook, J. M., (1997) J. Org. Chem, 62, pp. 44-61
Liu, J. -J., Hino, T., Tsuruoka, A., Harada, N., Nakagawa, M., (2000) J. Chem. Soc., Perkin Trans. 1, 20, pp. 3487-3494
Synthesis Of Novel Indole-Based Ring Systems By Acid-Catalyzed Condensation From A-Amino Aldehydes And L-Trp-Ome