Synthesis of imidazo[2,1-b]thiazoles linked to an unprotected carbohydrate moiety
Two series of imidazo[2,1-b]thiazoles substituted on C-3 or C-5 with an unprotected carbohydrate moiety were synthesized. Different protective groups for position 3 of the carbohydrate moiety were tested (acetyl, tert-butyldimethylsilyl (TBDMS), and p-methoxybenzyl (PMB)) and the latter turn out to...
Guardado en:
| Autor principal: | |
|---|---|
| Otros Autores: | , |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2012
|
| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 07679caa a22011417a 4500 | ||
|---|---|---|---|
| 001 | PAPER-23401 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518205504.0 | ||
| 008 | 190411s2012 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-84862023694 | |
| 024 | 7 | |2 cas |a Carbohydrates; Imidazoles; Thiazoles | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a CRBRA | ||
| 100 | 1 | |a Barradas, J.S. | |
| 245 | 1 | 0 | |a Synthesis of imidazo[2,1-b]thiazoles linked to an unprotected carbohydrate moiety |
| 260 | |c 2012 | ||
| 270 | 1 | 0 | |m D'Accorso, N.B.; Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: norma@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Jaguelin, S., Robert, A., Gayral, P., (1991) Eur. J. Med. Chem., 26, pp. 51-57 | ||
| 504 | |a Gowen, B.B., Bray, M., (2011) Future Microbiol., 6, pp. 1429-1441 | ||
| 504 | |a Jain, K.S., Bariwal, J.B., Kathiravan, M.K., Phoujdar, M.S., Sahne, R.S., Chauhan, B.S., Shah, A.K., Yadav, M.R., (2008) Bioorg. Med. Chem., 16, pp. 4759-4800 | ||
| 504 | |a Andreani, A., Burnelli, S., Granaiola, M., Guardigli, M., Leoni, A., Locatelli, A., Morigi, R., Roda, A., (2008) Eur. J. Org. Chem., 43, pp. 657-661 | ||
| 504 | |a Andreani, A., Granaiola, M., Guardigli, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Roda, A., (2005) Eur. J. Org. Chem., 40, pp. 1331-1334 | ||
| 504 | |a Güzeldemirci, N.U., Küçükbasmaci, Ö., (2010) Eur. J. Org. Chem., 45, pp. 63-68 | ||
| 504 | |a Andreani, A., Rambaldi, M., Leoni, A., Locatelli, A., Andreani, F., Gehret, J.-C., (1996) Pharm. Acta Helv., 71, pp. 247-252 | ||
| 504 | |a Andreani, A., Rambaldi, M., Locatelli, A., Bossa, R., Fraccari, A., Galatulas, I.J., (1992) Med. Chem., 35, pp. 4634-4637 | ||
| 504 | |a Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Garaliene, V., Masotti, L.J., (2005) Med. Chem., 48, pp. 5604-5607 | ||
| 504 | |a Gürsoy, E., Güzeldemirci, N.U., (2007) Eur. J. Med. Chem., 42, pp. 320-326 | ||
| 504 | |a Andreani, A., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Recanatini, M., Garaliene, V., (2000) Bioorg. Med. Chem., 8, pp. 2359-2366 | ||
| 504 | |a Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Varoli, L., Shoemaker, R.H., (2011) Eur. J. Med. Chem., 46, pp. 4311-4323 | ||
| 504 | |a Park, J.-H., El-Gamal, M.I., Lee, Y.S., Oh, C.-H., (2011) Eur. J. Med. Chem., 46, pp. 5769-5777 | ||
| 504 | |a Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Recanatini, M., Bergamini, C., (2004) Bioorg. Med. Chem., 12, pp. 5525-5532 | ||
| 504 | |a Budriesi, R., Ioan, P., Locatelli, A., Cosconati, S., Leoni, A., Ugenti, M.P., Andreani, A., Chiarini, A.J., (2008) Med. Chem., 51, pp. 1592-1600 | ||
| 504 | |a Barradas, J.S., Errea, M.I., D'Accorso, N.B., Sepúlveda, C.S., Talarico, L.B., Damonte, E.B., (2008) Carbohydr. Res., 343, pp. 2468-2474 | ||
| 504 | |a Barradas, J.S., Errea, M.I., D'Accorso, N.B., Sepúlveda, C.S., Damonte, E.B., (2011) Eur. J. Med. Chem., 46, pp. 259-264 | ||
| 504 | |a Peters, C.J., (2002) Curr. Top. Microbiol. Immunol., 262, pp. 65-74 | ||
| 504 | |a Schmidt, O.T., (1963) Methods in Carbohydrate Chemistry, 2. , Academic Press: NewYork | ||
| 504 | |a Corey, E.J., Venkateswarlu, A., (1972) J. Am. Chem. Soc., 94, pp. 6190-6191 | ||
| 504 | |a Takaku, H., Kamaike, K., Tsuchiya, H., (1984) J. Org. Chem., 49, pp. 51-56 | ||
| 504 | |a Kim, K.S., Song, Y.H., Lee, B.H., Hahn, C.S., (1986) J. Org. Chem., 51, pp. 404-407 | ||
| 504 | |a Hanessian, S., Ponpipom, M.M., Lavallee, P., (1972) Carbohydr. Res., 24, pp. 45-56 | ||
| 504 | |a Dess, D.B., Martin, J.C., (1983) J. Org. Chem., 48, pp. 4155-4156 | ||
| 504 | |a More, J.D., Finney, N.S., (2002) Org. Lett., 4, pp. 3001-3003 | ||
| 504 | |a Landreau, C., Deniaud, D., Reliquet, A., Meslin, J.C., (2003) Eur. J. Org. Chem., 2003, pp. 421-424 | ||
| 504 | |a Landreau, C., Deniaud, D., Meslin, J.C., (2003) J. Org. Chem., 68, pp. 4912-4917 | ||
| 504 | |a Leblanc, Y., Fitzsimmons, B.J., Adams, J., Perez, F., Rokach, J., (1986) J. Org. Chem., 51, pp. 789-793 | ||
| 504 | |a Yan, L., Kahne, D., (1995) Synlett, p. 524 | ||
| 520 | 3 | |a Two series of imidazo[2,1-b]thiazoles substituted on C-3 or C-5 with an unprotected carbohydrate moiety were synthesized. Different protective groups for position 3 of the carbohydrate moiety were tested (acetyl, tert-butyldimethylsilyl (TBDMS), and p-methoxybenzyl (PMB)) and the latter turn out to be the best strategy to obtain the desired products. Full deprotection of the carbohydrate was performed successfully in only one step. © 2012 Elsevier Ltd. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica | ||
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: The authors acknowledge Agencia Nacional de Promoción Científica y Tecnológica, Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET) and Universidad de Buenos Aires (UBA) from Argentina for financial support. N.B.D. is member of Research Career from CONICET and J.S.B. has a fellowship from CONICET. | ||
| 593 | |a Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina | ||
| 593 | |a Departamento de Ingeniería Química, Instituto Tecnológico de Buenos Aires, Av. Eduardo Madero 399, 1106 Buenos Aires, Argentina | ||
| 593 | |a National Research Council of Argentina (CONICET), Argentina | ||
| 690 | 1 | 0 | |a CARBOHYDRATES |
| 690 | 1 | 0 | |a HETEROCYCLES |
| 690 | 1 | 0 | |a IMIDAZO[2,1-B]THIAZOLES |
| 690 | 1 | 0 | |a PROTECTIVE GROUPS |
| 690 | 1 | 0 | |a DEPROTECTION |
| 690 | 1 | 0 | |a HETEROCYCLES |
| 690 | 1 | 0 | |a IMIDAZO[2,1-B]THIAZOLES |
| 690 | 1 | 0 | |a ONE STEP |
| 690 | 1 | 0 | |a P-METHOXYBENZYL |
| 690 | 1 | 0 | |a PROTECTIVE GROUP |
| 690 | 1 | 0 | |a TERT-BUTYLDIMETHYLSILYL |
| 690 | 1 | 0 | |a ORGANIC COMPOUNDS |
| 690 | 1 | 0 | |a SYNTHESIS (CHEMICAL) |
| 690 | 1 | 0 | |a CARBOHYDRATES |
| 690 | 1 | 0 | |a ACETIC ACID DERIVATIVE |
| 690 | 1 | 0 | |a BENZYL DERIVATIVE |
| 690 | 1 | 0 | |a CARBOHYDRATE |
| 690 | 1 | 0 | |a HETEROCYCLIC COMPOUND |
| 690 | 1 | 0 | |a IMIDAZO[2,1 B]THIAZOLE DERIVATIVE |
| 690 | 1 | 0 | |a SILANE DERIVATIVE |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CARBOHYDRATE SYNTHESIS |
| 690 | 1 | 0 | |a DEPROTECTION REACTION |
| 690 | 1 | 0 | |a ONE POT SYNTHESIS |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a QUANTUM YIELD |
| 690 | 1 | 0 | |a REACTION ANALYSIS |
| 690 | 1 | 0 | |a CARBOHYDRATES |
| 690 | 1 | 0 | |a IMIDAZOLES |
| 690 | 1 | 0 | |a MOLECULAR STRUCTURE |
| 690 | 1 | 0 | |a STEREOISOMERISM |
| 690 | 1 | 0 | |a THIAZOLES |
| 700 | 1 | |a Errea, M.I. | |
| 700 | 1 | |a D'Accorso, N.B. | |
| 773 | 0 | |d 2012 |g v. 355 |h pp. 79-86 |p Carbohydr. Res. |x 00086215 |w (AR-BaUEN)CENRE-301 |t Carbohydrate Research | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-84862023694&doi=10.1016%2fj.carres.2012.04.011&partnerID=40&md5=9a54090d3def26be03204aa9c0f4f724 |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1016/j.carres.2012.04.011 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00086215_v355_n_p79_Barradas |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v355_n_p79_Barradas |y Registro en la Biblioteca Digital |
| 961 | |a paper_00086215_v355_n_p79_Barradas |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 963 | |a VARI | ||
| 999 | |c 84354 | ||