Synthesis Of Novel Indole-Based Ring Systems By Acid-Catalyzed Condensation From A-Amino Aldehydes And L-Trp-Ome (262 views)
European Journal Of Organic Chemistry (ISSN: 1434-193x), 2008; 11: 1983-1992.
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Paper type: Journal Article,
Impact factor: 3.016, 5-year impact factor: 2.853
Url: Not available.
Keywords: Amino Aldehydes, Catalysis, Condensation Reactions, Heterocycles, Indoles,
Affiliations:
*** IBB - CNR ***
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
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
Vojkovsky, T., Weinchsel, A., Patek, M., (1998) J. Org. Chem, 63, pp. 3162-3163
Hili, R., Yudin, A.K., (2006) J. Am. Chem. Soc, 128, pp. 14772-14773
Ducrot, P., Rabhi, C., Thal, C., (2000) Tetrahedron, 56, pp. 2683-2692
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
European Journal Of Organic Chemistry (ISSN: 1434-193x), 2008; 11: 1983-1992.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 3.016, 5-year impact factor: 2.853
Url: Not available.
Keywords: Amino Aldehydes, Catalysis, Condensation Reactions, Heterocycles, Indoles,
Affiliations:
*** IBB - CNR ***
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
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
Vojkovsky, T., Weinchsel, A., Patek, M., (1998) J. Org. Chem, 63, pp. 3162-3163
Hili, R., Yudin, A.K., (2006) J. Am. Chem. Soc, 128, pp. 14772-14773
Ducrot, P., Rabhi, C., Thal, C., (2000) Tetrahedron, 56, pp. 2683-2692
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
Acid-catalysed condensation of tryptophan with different α-amino aldehyde derivatives has been explored as a useful route to the synthesis of novel amino acid derived heterocycles and peptidomimetic scaffolds. By this approach, compounds containing a tetrahydro-β-carboline and a novel octahydropyrrolo[ 3′,2′:3,4]pyrrolo[2,3-b]indole system have been efficiently synthesized. Here we report the characterization of these new compounds and preliminary studies of the reactivity of the tetrahydro-β- carboline system. © Wiley-VCH Verlag GmbH & Co. KGaA.
Acid-catalysed condensation of tryptophan with different α-amino aldehyde derivatives has been explored as a useful route to the synthesis of novel amino acid derived heterocycles and peptidomimetic scaffolds. By this approach, compounds containing a tetrahydro-β-carboline and a novel octahydropyrrolo[ 3′,2′:3,4]pyrrolo[2,3-b]indole system have been efficiently synthesized. Here we report the characterization of these new compounds and preliminary studies of the reactivity of the tetrahydro-β- carboline system. © Wiley-VCH Verlag GmbH & Co. KGaA.
Synthesis Of Novel Indole-Based Ring Systems By Acid-Catalyzed Condensation From A-Amino Aldehydes And L-Trp-Ome
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Synthesis Of Novel Indole-Based Ring Systems By Acid-Catalyzed Condensation From A-Amino Aldehydes And L-Trp-Ome
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* (E)-2-Cyano-3-(5 Alpha-Piperidin-1-Yl-2, 2 Alpha-Bithien-5-Yl)acrylic Acid: A Fluorescent Probe For Detecting Prefibrillar Oligomers (420 views)
European Journal Of Organic Chemistry (ISSN: 1434-193x), 2013 Jun; (18): 3635-3639.
Impact Factor: 3.154
View Export to BibTeX Export to EndNote
Gomez-monterrey Isabel M, Campiglia P, Bertamino A, Aquino C, Mazzoni O, Diurno Maria V, Iacovino R, Saviano M, Sala M, Novellino E, Grieco P
* Synthesis of Novel Indole-Based Ring Systems by Acid-Catalysed Condensation from α-Amino Aldehydes and L-Trp-OMe (237 views)
Eur J Org Chem (ISSN: 1099-0690), 2008; 2008(11): 1983-1992.
Impact Factor: 0
View Export to BibTeX Export to EndNote
Santoro F, Improta R, Lami A, Bloino J, Barone V
* Effective method to compute Franck-Condon integrals for optical spectra of large molecules in solution (246 views)
J Chem Phys (ISSN: 0021-9606, 0897-690online), 2007 Feb 28; 126(8): 084509-084509.
Impact Factor: 3.044
View Export to BibTeX Export to EndNote
3 Records (2 excluding Abstracts).
Total impact factor: 6.198 (3.154 excluding Abstracts).
Total 5 year impact factor: 6.044 (3.001 excluding Abstracts).
Total impact factor: 6.198 (3.154 excluding Abstracts).
Total 5 year impact factor: 6.044 (3.001 excluding Abstracts).
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