Abstract:
Novel 10-{[3-(6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)- 4,5-dihydro-5-isoxazolyl]methyl}-9(10H)-acridinone derivatives (13-16) were synthesized by 1,3-dipolar cycloaddition using the carbohydrate derivative as dipole and different 10-allyl-9(10H)-acridinone derivatives (9-12) as dipolarophiles. The new cycloadducts as well as the dipolarophiles precursors were characterized spectroscopically. Copyright © Taylor & Francis Group, LLC.
Registro:
| Documento: |
Artículo
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| Título: | Synthesis of novel carbohydrate acridinone derivatives with potential biological activities using 1,3-dipolar cycloaddition |
| Autor: | Fascio, M.L.; D'Accorso, N.B.; Pellón, R.F.; Docampo, M.L. |
| Filiación: | CIHIDECAR-CONICET, Department of Organic Chemistry, FCEyN-Buenos Aires University, Buenos Aires, Argentina
Center of Pharmaceutical Chemistry, Havana, Cuba
Faculty of Exact and Natural Science, Department of Organic Chemistry, Ciudad Universitaria, Buenos Aires, Argentina
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| Palabras clave: | 1,3-dipolar cycloaddition; Acridinones; Carbohydrates; Isoxazolines; N-allylation; 10 [[3 (6 hydroxy 2,2 dimethyltetrahydrofuro[2,3 d][1,3]dioxol 5 yl) 4,5 dihydro 5 isoxazolyl]methyl] 4 methoxy 9(10h) acridinone; 10 [[3 (6 hydroxy 2,2 dimethyltetrahydrofuro[2,3 d][1,3]dioxol 5 yl) 4,5 dihydro 5 isoxazolyl]methyl] 9(10h) acridinone; 10 allyl 3 chloro 5 methoxy 9(10h) acridinone; 10 allyl 3 chloro 9(10h) acridinone; 10 allyl 4 methoxy 9(10h) acridinone; 10 allyl 9(10h) acridinone; 3 chloro 10 [[3 ( hydroxy 2,2 dimethyltetrahydrofuro[2,3 d][1,3]dioxol 5 yl) 4,5 dihydro 5 isoxazolyl]methyl] 6 methoxy 9(10h) acridinone; 3 chloro 10 [[3 (6 hydroxy 2,2 dimethyltetrahydrofuro[2,3 d][1,3]dioxol 5 yl) 4,5 dihydro 5 isoxazolyl]methyl] 9(10h) acridinone; acridinone derivative; carbohydrate derivative; organic compound; unclassified drug; article; cycloaddition; drug activity; drug determination; drug structure; drug synthesis; spectroscopy; structure analysis |
| Año: | 2007
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| Volumen: | 37
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| Número: | 23
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| Página de inicio: | 4209
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| Página de fin: | 4217
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| DOI: |
http://dx.doi.org/10.1080/00397910701575178 |
| Título revista: | Synthetic Communications
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| Título revista abreviado: | Synth. Commun.
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| ISSN: | 00397911
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| CODEN: | SYNCA
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| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397911_v37_n23_p4209_Fascio |
Referencias:
- Fujiwara, M., Okamoto, M., Okamoto, M., Watanabe, M., Machida, H., Shigeta, S., Konno, K., Baba, M., Acridone derivatives are selective inhibitors of HIV-1 replication in chronically infected cells (1999) Antiviral Res, 43, pp. 179-189
- Akanitapichat, P., Bastow, K.F., The antiviral agent 5-chloro-1,3- dihydroxyacridone interferes with assembly and maturation of herpes simplex virus (2002) Antiviral Res, 53, pp. 113-126
- Lowden, C.T., Bastow, K.F., Cell culture replication of herpes simplex virus and or human cytomegalovirus is inhibited by 3,7-dialkoxylated, 1-hydroxyacridone derivatives (2003) Antiviral Res, 59, pp. 143-154
- Akanitapichat, P., Lowden, C.T., Bastow, K.F., 1,3-Dihydroxyacridone derivatives as inhibitors of herpes virus replication (2000) Antiviral Res, 45, pp. 123-134
- Vance, J.R., Bastow, K.F., Inhibition of DNA topoisomerase II catalytic activity by the antiviral agents 7-chloro-1,3-dihydroxyacridone and 1,3,7-trihydroxyacridone (1999) Biochem. Pharmacol, 58, pp. 703-708
- Lowden, C.T., Bastow, K.F., Anti-herpes simplex virus activity of substituted 1-hydroxyacridones (2003) J. Med. Chem, 46, pp. 5015-5020
- Krishnegowda, G., Thimmaiah, P., Hegde, R., Dass, C., Houghton, P.J., Thimmaiah, K.N., Synthesis and chemical characterization of 2-methoxy-N10 substituted acridones needed to reverse vinblastine resistance in multidrug resistant (MDR) cancer cells (2002) Bioorg. Med. Chem, 10, pp. 2367-2380
- Fascio, M.L., Montesano, V.J., D'Accorso, N.B., Synthesis and characterization of some 3-glycosyl-5-substituted-2-isoxazoles with potential biological activities (2000) J. Carbohydr. Chem, 19, pp. 393-398
- Fascio, M.L., D'Accorso, N.B., A facile synthesis of 3-glycosyl-5-substituted-2-isoxazoles (2001) Synth. Commun, 31, pp. 1913-1920
- Martinez Esperon, M.F., Fascio, M.L., D'Accorso, N.B., A synthetic pathway to obtain derivatives containing isoxazole and tetrazole rings joined by a carbohydrate tether (2002) J. Heterocycl. Chem, 39, pp. 221-224
- Fascio, M.L., D'Accorso, N.B., Synthesis of 3-glycosyl-5- substituted-2-isoxazolines (1996) J. Heterocycl. Chem, 33, pp. 1573-1577
- Fascio, M.L., Montesano, V.J., D'Accorso, N.B., 1,3-Dipolar cycloaddition of 1,2-O-isopropylidene-α-D-xylo- pentadialdo-1,4-furanosenitrile oxide to some alkenes (1998) J. Heterocycl. Chem, 35, pp. 103-107
- Fascio, M.L., Alvarez-Larena, A., D'Accorso, N.B., Synthesis, high-resolution NMR spectroscopic analysis, and single-crystal X-ray diffraction of isoxazoline tetracycles (2002) Carbohydr. Res, 337, pp. 2419-2427
- Pellón, R.F., Carrasco, R., Rodés, L., Synthesis of N-phenylantranilic acids using water as solvent (1993) Synth. Commun, 23, pp. 1447-1453
- Docampo, M.L., Pellon, R.F., Synthesis of N-phenylanthranilic acid derivatives using water as solvent in the presence of ultrasound irradiation (2003) Synth. Commun, 33, pp. 1771-1775
- Xuárez, L., Pellón, R., Fascio, M., Montesano, V., D'Accorso, N., Synthesis of N-allyl and N-propadienyl acridones using phase-transfer catalysis (2004) Heterocycles, 63, pp. 23-28
- Acheson, R.M., Orgel, L.E., (1956) The Chemistry of Heterocyclic Compounds: Acridines, 9, pp. 122-145. , Interscience: New York
- Wang, C., Hang, T., Zhang, H., Microwave-promoted N-alkylation of acridones without solvent (2003) Synth. Commun, 33, pp. 451-456
Citas:
---------- APA ----------
Fascio, M.L., D'Accorso, N.B., Pellón, R.F. & Docampo, M.L.
(2007)
. Synthesis of novel carbohydrate acridinone derivatives with potential biological activities using 1,3-dipolar cycloaddition. Synthetic Communications, 37(23), 4209-4217.
http://dx.doi.org/10.1080/00397910701575178---------- CHICAGO ----------
Fascio, M.L., D'Accorso, N.B., Pellón, R.F., Docampo, M.L.
"Synthesis of novel carbohydrate acridinone derivatives with potential biological activities using 1,3-dipolar cycloaddition"
. Synthetic Communications 37, no. 23
(2007) : 4209-4217.
http://dx.doi.org/10.1080/00397910701575178---------- MLA ----------
Fascio, M.L., D'Accorso, N.B., Pellón, R.F., Docampo, M.L.
"Synthesis of novel carbohydrate acridinone derivatives with potential biological activities using 1,3-dipolar cycloaddition"
. Synthetic Communications, vol. 37, no. 23, 2007, pp. 4209-4217.
http://dx.doi.org/10.1080/00397910701575178---------- VANCOUVER ----------
Fascio, M.L., D'Accorso, N.B., Pellón, R.F., Docampo, M.L. Synthesis of novel carbohydrate acridinone derivatives with potential biological activities using 1,3-dipolar cycloaddition. Synth. Commun. 2007;37(23):4209-4217.
http://dx.doi.org/10.1080/00397910701575178
