Synthesis of novel carbohydrate acridinone derivatives with potential biological activities using 1,3-dipolar cycloaddition

Synthetic Communications

Volumn 37, Issue 23, 2007, Pages 4209-4217

  Fascio, Mirta L ^a   D'Accorso, Norma Beatriz ^a   Pellón, Rolando F ^b   Docampo, Maite L ^b  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^b Center of Pharmaceutical Chemistry Cuba   (Cuba)

Author keywords

1,3 dipolar cycloaddition; Acridinones; Carbohydrates; Isoxazolines; N allylation

Indexed keywords

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;

EID: 37049020226     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701575178     Document Type: Article

References (18)

1. Fujiwara, M.; Okamoto, M.; Okamoto, M.; Watanabe, M.; Machida, H.; Shigeta, S.; Konno, K.; Yokota, T.; Baba, M. Acridone derivatives are selective inhibitors of HIV-1 replication in chronically infected cells. Antiviral Res. 1999, 43, 179-189.
2. Akanitapichat, P.; Bastow, K. F. The antiviral agent 5-chloro-1,3- dihydroxyacridone interferes with assembly and maturation of herpes simplex virus. Antiviral Res. 2002, 53, 113-126.
3. 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. Antiviral Res. 2003, 59, 143-154.
4. Akanitapichat, P.; Lowden, C. T.; Bastow, K. F. 1,3-Dihydroxyacridone derivatives as inhibitors of herpes virus replication. Antiviral Res. 2000, 45, 123-134.
5. 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. Biochem. Pharmacol. 1999, 58, 703-708.
6. Lowden, C. T.; Bastow, K. F. Anti-herpes simplex virus activity of substituted 1-hydroxyacridones. J. Med. Chem. 2003, 46, 5015-5020.
7. 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. Bioorg. Med. Chem. 2002, 10, 2367-2380.
8. (a) 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. J. Carbohydr. Chem. 2000, 19, 393-398;
9. (b) Fascio, M. L.; D'Accorso, N. B. A facile synthesis of 3-glycosyl-5-substituted-2-isoxazoles. Synth. Commun. 2001, 31, 1913-1920;
10. (c) 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. J. Heterocycl. Chem. 2002, 39, 221-224;
11. (d) Fascio, M. L.; D'Accorso, N. B. Synthesis of 3-glycosyl-5- substituted-2-isoxazolines. J. Heterocycl. Chem. 1996, 33, 1573-1577;
12. (e) 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. J. Heterocycl. Chem. 1998, 35, 103-107;
13. (f) 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. Carbohydr. Res. 2002, 337, 2419-2427.
14. (a) Pellón, R. F.; Carrasco, R.; Rodés, L. Synthesis of N-phenylantranilic acids using water as solvent. Synth. Commun. 1993, 23, 1447-1453;
15. (b) Docampo, M. L.; Pellon, R. F. Synthesis of N-phenylanthranilic acid derivatives using water as solvent in the presence of ultrasound irradiation. Synth. Commun. 2003, 33, 1771-1775.
16. Xuárez, L.; Pellón, R.; Fascio, M.; Montesano, V.; D'Accorso, N. Synthesis of N-allyl and N-propadienyl acridones using phase-transfer catalysis. Heterocycles 2004, 63, 23-28.
17. Acheson, R. M.; Orgel, L. E. The Chemistry of Heterocyclic Compounds: Acridines; Interscience: New York, 1956, Vol. 9, pp. 122-145.
18. Wang, C.; Hang, T.; Zhang, H. Microwave-promoted N-alkylation of acridones without solvent. Synth. Commun. 2003, 33, 451-456.