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학술연구/단체지원/교육 등 연구자 활동을 지속하도록 DBpia가 지원하고 있어요.
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초록· 키워드
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We developed a convenient synthetic route to 3-alkylated 2-phenyl-4-quinolone derivatives (4a-h and 5a-c), which were expected to retain antitumor activity. A series of 2,3-dihydro-2-hydroxy-2-phenyl-4-quinolones (3a-h) was synthesized through dehydration, dealcoholation and hydration using acid-catalyzed one-pot reaction from anilines and ethyl benzoylacetates. 3-Methyl (or 3,3-dimethyl)-2-phenyl-4-quinolone derivatives 4 and 5 were synthesized from 3a-h through the methylation using methyl iodide. Formation of quinolone nucleus was undertaken with p-toluenesulfonic acid (p-TSA) at $90{\sim}110^{\circ}C$ in toluene for 3${\sim}$7.5 hr over the Dean-Stark apparatus. The key intermediates in these preparations are ${\beta}$-ketoesters 2a-h, which can be readily obtained from the corresponding anilines 1a-e by reaction with ethyl bezoylacetates.
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참고문헌 (11)
참고문헌 신청
Seo, H. J. / 2001 / Eupatilin, a pharmacologically active flavone derived from artemisia plants, induces apoptosis in human promyelocytic leukemia cells / Mutation Rearch 496:191
Bauvois, B. / 2003 / Synthesis and biological evaluation of novel flavone-8-acetic acid derivatives as reversible inhibitors of aminopeptidase N/CD13 / J. Med. Chem 46:3900
Gobbi, S. / 2003 / Synthesis and biological evaluation of 3-alkoxy-analogues of flavone-8-acetic acid / J. Med. Chem 46:3662
Li, L. / 1994 / 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
Li, L. / 1994 / Antitumor agents. 155. Synthesis and biological evaluation of 3',6,7-substituted 2- phenyl-4-quinolones as antimicrotubule agents / J. Med. Chem 37:3400
Bauvois, B. / 2003 / Synthesis and biological evaluation of novel flavone-8-acetic acid derivatives as reversible inhibitors of aminopeptidase N/CD13 / J. Med. Chem 46:3900
Gobbi, S. / 2003 / Synthesis and biological evaluation of 3-alkoxy-analogues of flavone-8-acetic acid / J. Med. Chem 46:3662
Li, L. / 1994 / 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
Li, L. / 1994 / Antitumor agents. 155. Synthesis and biological evaluation of 3',6,7-substituted 2- phenyl-4-quinolones as antimicrotubule agents / J. Med. Chem 37:3400
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