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Synthesis of Asymmetric Dimer of Quinolone Derivatives Using p-TSA  

박명숙 (덕성여자대학교 약학대학)
Publication Information
YAKHAK HOEJI / v.48, no.3, 2004 , pp. 202-206 More about this Journal
Abstract
New asymmetric dimers, N,N'-dialkyl-4'-hydroxy-4-oxo-2,2',3,3'-tetrahydro-2,2'-diphenyl-4,4'-quinolones 3a-f were synthesized through the dehydration and dea1coholation of N-alkylanilines and ethyl benzoylacetate. Dimers 3a-f were identified by NMR, IR and GC-MS. A series of dimer 3a-f has been synthesized using acid-catalyzed one-pot reaction that involved the condensation, cyc1ization and dimerization. Similarly, the 6,6'-methoxy (or 7,7'-methoxy) substituted dimers were prepared from N-alkyl-meta-(or para)-anisidines. Formation of dimers was undertaken with p-toluenesulfonic acid (p-TSA) at 90∼11$0^{\circ}C$ in toluene for 2∼6 hours over the Dean-Stark apparatus.
Keywords
asymmetric dimer; 2,3-dihydro-2-phenyl-4-quinolones; synthesis; antiinflammatory; dimerization;
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1 Lin, Y. M., Zhou, Y., Flavin, M. T. and Zhou, L. M. : Chalcones and flavonoids as anti-tuberculosis agents. Bioorganic & Medicinal Chemistry 10, 2795 (2002)   DOI   ScienceOn
2 Sartor L., Pezzato, E., Dell’Aica, I., Caniato, R., Biggin, S. and Garbisa, S. : Inhibition of matrix-proteases by polyphenols: chemical insights for anti-inflammatory and anti-invasion drug design. Biochemical Pharmacology 64, 229 (2002)   DOI   ScienceOn
3 Li, L., Wang, H. K., Kuo, S. C., Wu, T. S., Mauger, A., Lin, C. M., Hamel, E. and Lee, K. H. : Antitumor agents. 155. Synthesis and biological evaluation of 3',6,7-substituted 2-phenyl-4-quinolones as antimicrotubule agents. J. Med. Chem. 37, 3400 (1994)   DOI   ScienceOn
4 Xia, Y., Yang, Z. Y., Xia, P., Bastow, K. E, Nakanishi, P. N., Hamel, E., Brossi, A. and Lee, K. H. : Antitumor agents. part 226: synthesis and cytotoxicity of 2-phenyl-4-quinolone acetic acids and their esters. Bioorganic & Medicinal Chemistry Letters 13, 2891 (2003)
5 Nijveldt, R. J., Nood, E., Hoorn, D. EC, Boelens, P., Norren, K. and Leeuwen, P. : Flavonoids: a review of probable mechanisms of action and potential applications. Am. J. Clin. Nutr. 74, 418 (2001)
6 Dao, T. T., Kim S. B., Sin K. S., Kim, S. H., Kim, H. P. and Park, H. : Synthesis and biological activity of 8-arylflavones. Arch. Pharm. Res. 27, 278 (2004)
7 Wu, E. S. C., Loch III, J., Toder, B. H., Borrelli, A. R., Gawlak, D., Radow, L A. and Gensmantel, N. P. : Flavones. 3. Synthesis, biological activities, and conformational analysis of isoflavone derivatives and related compounds. J. Med. Chem. 35, 3519 (1992)
8 Chi, Y. S., Lim, H., Park, H. and Kim, H. P. : Effects of wogonin, a plant flavone from Scutellaria radix, on skin inflammation: in vivo regulation of inflammation-associated gene expression. Biochemical Pharmacology 66, 1271 (2003)   DOI   ScienceOn
9 Ballesteros, J. E., Sanz, M.J., Ubeda, A., Miranda, M. A., Iborra, S., Paya, M. and Alcaraz, M. J. : Synthesis of pharmacological evaluation of 2'-hydroxychalcones and flavones as inhibitors of inflammatory mediators generation. J. Med. Chem. 35, 2974(1995)
10 Rotelli, A. E., Gurardia, T., Juarez, A. O., Rocha, N. E. and Pelzer L. E. : Comparative study of flavonoids in experimental models of inflammation. Pharmacological Research 48, 601 (2003)   DOI   ScienceOn
11 Park, M. S. and Lee, J. I. : Synthesis of new 2,3-dihydro-2phenyl- 4-quinolone derivatives; aza analogs of flavanone. Bull. Korean Chem. Soc. 25, in press (2004)
12 Dao, T. T., Chi, Y. S., Kim, J., Kim, H. P. and Park, H. : Synthesis and $PGE_2$ inhibitory activity of 5,7-dihydroxy-f1avones and their O-methylated flavone analogs. Arch. Pharm. Res. 26, 345 (2003)   DOI   ScienceOn
13 Harhorne, J. B. and Williams, C. A. : Antocyanins and other flavonoids. Nat. Prod. Rep. 18, 310 (2001)   DOI   ScienceOn
14 Kuo, S. C., Lee, H. Z., Juang, J. P., Lin, Y. T, Wu, T. S., Chang, J. J., Lednicer, D., Paull, K. D., Lin, C. M., Hamel, E. and Lee, K. H. : Synthesis and cytotoxicity of 1,6,7,8-substituted 2-(4'substituted phenyl)-4-quinolones and related compounds: Identification as antimitotic agents interacting with tubulin.J. Med. Chem. 36, 1146 (1993)
15 Schutz, B. A, Wright, A. D., Rali T. and Sticher O. : Prenylated f1avanones from leaves of Maclaranga Pleiostemona. PhytochemistnI 40, 1273 (1995)   DOI   ScienceOn
16 Park，B. K., Heo, M. Y., Park, H. and Kim, H. P. : Inhibition of TPA-induced cyclooxygenase-2 expression and skin inflammation in mice by wogonin, a plant flavone from Scutellana radix. European J. Pharmacology 425, 153 (2001)
17 Jang, D. S., Cuendet, M., Hawthorne, M., Kardono, L. B. S., Kawanishi, K., Fong, H. H. S., Mehta, R. G., Pezzuto, J. M. and Kinghorn, A. D. : Prenylated flavonoids of the leaves of Mascaranga conifera with inhibitory activity against cyclooxygenase-2. Phytochemistry 61, 867 (2002)   DOI   ScienceOn
18 Li, L., Wang, H. K., Kuo, S. C., Wo, T. S., Lednicer, D., Lin, C. M., Hamel, E. and Lee, K. H. : Antitumor agents. 150. 2’,3’,4’,5’,5,6,7-substituted 2-phenyl-4-quinolones and related compounds: their synthesis, cytotoxicity, and inhibition of tubulin polymerization. J. Med. Chem. 37, 1126 (1994)
19 Watterson, S. H., Carlsen, M., Dhar, T. G. M., Shen, Z., Pitts, W. J., Gu, H. H., Norris , D., Chorba, J., Chen, P., Cheny, D., Witmer M., Fleener, C. A., Rouleau, K., Townsend, R., Hollenbaugh, D. L. and Iwanowicz, E. J. : Novel inhibitors of IMPDH: a highly potent and selective quinolone-based series. Bioorganic & Medicinal Chemistry Letters 13, 543 (2003).   DOI   ScienceOn
20 Olszanecki, R., Gebska, A., Kozlovski, V. I. and Gryglewski, R. J. : Flavonoids and nitric oxide synthase. J. Physiology and Pharmacology 53, 571 (2002)