Synthesis and activity of substituted anthraquinones against a human filarial parasite, Brugia malayi

Journal of Medicinal Chemistry

Volumn 48, Issue 8, 2005, Pages 2822-2830

  Dhananjeyan, Mugunthu R ^a   Milev, Youli P ^b   Kron, Michael A ^b   Nair, Muraleedharan G ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXY 2 METHOXY 3 METHYLANTHRAQUINONE; 1 HYDROXY 2,8 DIMETHOXY 3 METHYLANTHRAQUINONE; 1 METHYL 2,3 DIHYDROXYANTHRAQUINONE; 1 METHYL 2,3 DIMETHOXY 8 HYDROXYANTHRAQUINONE; 1 METHYL 2,3,8 TRIHYDROXYANTHRAQUINONE; 1,2 DIHYDROXY 3 METHYLANTHRAQUINONE; 1,2 DIMETHOXY 3 METHYLANTHRAQUINONE; 1,2,3 TRIHYDROXYANTHRAQUINONE; 1,2,3,5 TETRAHYDROXYANTHRAQUINONE; 1,2,5 TRIHYDROXYANTHRAQUINONE; 1,2,8 TRIHYDROXY 3 METHYLANTHRAQUINONE; 1,2,8 TRIHYDROXYANTHRAQUINONE; 1,3 DIHYDROXYANTHRAQUINONE; 1,3,5 TRIHYDROXYANTHRAQUINONE; 1,4,8 TRIHYDROXYANTHRAQUINONE; 1,8 DIHYDROXY 2 METHOXY 3 METHYLANTHRAQUINONE; 2,3,8 TRIHDYROXYANTHRAQUINONE; ALBENDAZOLE; ALIZARIN; ANTHRAQUINONE DERIVATIVE; QUINIZARIN; UNCLASSIFIED DRUG;

ARTICLE; BRUGIA MALAYI; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELEPHANTIASIS; FRIEDEL CRAFTS REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICROFILARIA; NONHUMAN; PARASITOSIS; PLANT ROOT; SCHISTOSOMA MANSONI; TREMATODE; WUCHERERIA BANCROFTI;

ANIMALS; ANTHRAQUINONES; BRUGIA MALAYI; EMBRYO, NONMAMMALIAN; FEMALE; FILARICIDES; HUMANS; LARVA; MALE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 17444392875     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0492655     Document Type: Article

References (23)

1. Ottesen, E. A. The Global Programme to Eliminate Lymphatic Filariasis. Trop. Med. Int. Health 2000, 5, 591-594.
2. Anonymous, The Global Alliance for the Elimination of Lymphatic Filariasis-Epidemiology, http://www.filariasis.org/ 2002).
3. Thomson, R. H. Naturally Occurring Quinonones; Academic Press: London, 1971; pp 367-535.
4. Tai, C. Y.; Chen, B. H. Analysis and Stability of Carotenoids in the Flowers of Daylily (Hemerocallis disticha) as Affected by Various Treatments. J. Agric. Food Chem. 2000, 48, 5962-5968.
5. Cichewicz, R. H.; Lim, K. C.; Mckerrow, J. H.; Nair, M. G. Kwanzaquinones A-G and other constituents of Hemerocallis filva 'Kwanzo' roots and their activity against the human pathogenic trematode Schistosoma mansoni. Tetrahedron 2002, 58, 8597-8606.
6. Nanba, Y.; Ono, T.; Okuda, Y. Catalyst for the preparation of anthraquinone. US Patent No. 3,870,655, 1975.
7. Rodriguez, F.; Burillo, J.; Adrados, L. F.; Tijero, J. F. Recovery of anthracene from coal tar by solvent extraction. Sep. Sci. Technol. 1989, 24, 275-289.
8. Boisvert, L.; Brassard, P. Regiospecific addition of monooxygenated dienes to halo quinones. J. Org. Chem. 1988, 53, 4052-4059.
9. Olah, G. A. Friedel-Crafts and related reactions; Wiley-Interscience: New York, 1964; Vol II, Part I.
10. Bensari, A.; Zaveri, N. T. Titanium (IV) chloride-mediated orthoacylation of phenols and naphthols. Synthesis 2003, 267-271.
11. Kotsuki, H.; Ohishi, T.; Inoue, M.; Kojima, T. A new convenient Friedel-Crafts alkylation of aromatic compounds with secondary alcohol methanesulfonates in the presence of scandium(III) trifluoromethanesulfonate or trifluoromethanesulfonic acid as the catalyst. Synthesis 1999, 603-606.
12. Kobayashi, S. Scandium Triflate in Organic Synthesis. Eur. J. Org. Chem. 1999, 15-27.
13. Devic, M. Process for the preparation of anthraquinone and its substituted derivatives. US Patent No. 4,379,092, 1983.
14. 3 catalyst for anthraquinone synthesis from benzene and phthalic anhydride reaction, Huaxue Shijie 1993, 34, 258-260.
15. Balasubramanian, S.; Nair, M. G. Process for the preparation of isoflavones. US Patent No. 5,981,775, 1999.
16. Balasubramanian, S.; Nair, M. G. An efficient one pot synthesis of isoflavones. Synth. Commun. 2000, 30, 469-484.
17. Balasubramanian, S.; Ward, D. L.; Nair, M. G. The first isolation and crystal structure of a boron difluoro complex (isoflavone yellow). Biologically active intermediates produced during isoflavone synthesis. Perkin Trans, 1 2000, 4, 567-570.
18. Akazawa, Y.; Nanba, T.; Nakanishi, Y. Manufacture of anthraquinone. Jpn. Kokai Tokkyo Koho, JP 61100543, 1986.
19. Huffman, J. W.; Starnes, J. J. Friedel-Crafts reaction of 3,4,4-trimethylbutyrolactone and benzene. J. Org. Chem. 1972, 37, 487-490.
20. Asaoka, M.; Miyake, K.; Takei, H. Synthesis of 7-hydroxyphthalides starting from unsaturated lactones via 2-trialkylsiloxyfurans. Chem. Lett. 1977, 167-170.
21. Eliel, E. L.; Burgstahler, A. W.; Rivard, D. W.; Haefele, L. The Methyl Esters of 3-Hydroxyphthalic Acid. Selective Reduction of Monomethyl Phthalates with LiAlH4. J. Am. Chem. Soc. 1955, 77, 5092-5095.
22. Pratt, D. S.; Perkins, G. A. Phthalic acid derivatives; constitution and color, v. some derivatives of tetrachloro- and tetraiodo phthalimides. J. Am. Chem. Soc. 1918, 40, 219-214.
23. Nasman, J.-H. N. A Versatile synthetic route to 3-hydroxyphthalic anhydride. Synthesis 1985, 788-789.