Synthesis and Cytotoxic Activity of Benzo[a]pyrano[3,2-h] and [2,3-i]xanthone Analogues of Psorospermine, Acronycine, and Benzo [a] acronycine
スポンサーリンク
概要
- 論文の詳細を見る
Condensation of 2-hydroxy-1-naphthalenecarboxylic acid with phloroglucinol afforded 9,11-dihydroxy-12H-benzo[α]xanthen-12-one (6). Construction of an additional dimethylpyran ring onto this skeleton, by alkylation with 3-chloro-3-methyl-1-butyne followed by Claisen rearrangement, gave access to 6-hydroxy-3,3-dimethyl-3H,7H-benzo[α]pyrano[3,2-h]xanthen-7-one (12) and 5-hydroxy-2,2-dimethyl-2H,6H-benzo[α]pyrano[2,3-i]xanthen-6-one (13), which were methylated into 6-methoxy-3,3-dimethyl-3H,7H-benzo[α]pyrano[3,2-h]xanthen-7-one (14) and 5-methoxy-2,2-dimethyl-2H,6H-benzo[a]pyrano[2,3-i]xanthen-6-one (15), respectively. Osmium tetroxide oxidation of 14 and 15 gave the corresponding (±)-cis-diols 16 and 17, which afforded the corresponding esters 18-21 upon acylation. Similarly, condensation of 2-hydroxy-1-naphthalenecarboxylic acid with 3,5-dimethoxyaniline gave 11-amino-9-methoxy-12H-benzo[α]xanthen-12-one (23) which was converted into 11-amino-9-hydroxy-12H-benzo[α]xanthen-12-one (24) upon treatment with hydrogen bromide in acetic acid. Alkylation with 3-chloro-3-methyl-1-butyne followed by Claisen rearrangement afforded 6-amino-3,3-dimethyl-3H,7H-benzo[α]pyrano[3,2-h]xanthen-7-one (25) and 5-amino-2,2-dimethyl-2H,6H-benzo[α]pyrano[2,3-i]xanthen-6-one (26). The new benzopyranoxanthone derivatives only displayed marginal antiproliferative activity when tested against L1210 and KB-3-1 cell lines. The only compounds found significantly active against L1210 cell line, 16 and 20, belong to the benzo[a]pyrano[3,2-h]xanthen-7-one series, which possess a pyran ring fused angularly onto the xanthone basic core.
- 公益社団法人日本薬学会の論文
- 2006-08-01
著者
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Koch Michel
Laboratoire De Pharmacognosie De I'universite Rene Descartes U.m.r. C.n.r.s. N° 8638 Faculte De
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Michel Sylvie
Laboratoire De Pharmacognosie De I'universite Rene Descartes U.m.r. C.n.r.s. N° 8638 Faculte De
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Koch M
Univ. Rene Descartes Paris Fra
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Pfeiffer Bruno
Institut De Recherches Servier Division Recherche Cancerologie
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TILLEQUIN Francois
Laboratoire de Pharmacognosie de l'Universite Paris Descartes
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PIERRE Alain
Institut de Recherches Servier, Division Recherche Cancerologie
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SITTISOMBUT Chavalit
Laboratoire de Pharmacognosie de l'Universite Rene Descartes, U.M.R.-C.N.R.S. n°8638, Faculte des Sc
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BOUTEFNOUCHET Sabrina
Laboratoire de Pharmacognosie de l'Universite Rene Descartes, U.M.R.-C.N.R.S. n°8638, Faculte des Sc
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TRINH VAN-DUFAT
Laboratoire de Pharmacognosie de l'Universite Rene Descartes, U.M.R.-C.N.R.S. n°8638, Faculte des Sc
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TIAN Wen
Laboratoire de Pharmacognosie de l'Universite Rene Descartes, U.M.R.-C.N.R.S. n°8638, Faculte des Sc
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Tian Wen
Laboratoire De Pharmacognosie De L'universite Rene Descartes U.m.r.-c.n.r.s. N°8638 Faculte Des
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Pierre Alain
Institut De Recherches Servier Division Recherche Cancerologie
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Mitaku S
Laboratory Of Pharmacognosy Department Of Pharmacy University Of Athens
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Trinh Van-dufat
Laboratoire De Pharmacognosie De L'universite Rene Descartes U.m.r.-c.n.r.s. N°8638 Faculte Des
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Tillequin Francois
Laboratoire De Pharmacognosie De L'universite Paris Descartes
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Tillequin F
Laboratoire De Pharmacognoise De 1'universite Rene Descartes Umr/cnrsn ^○8638 Faculte Des Scien
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Mitaku Sofia
Laboratory Of Pharmacognosy Department Of Pharmacy University Of Athens
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Sittisombut Chavalit
Laboratoire De Pharmacognosie De L'universite Rene Descartes U.m.r.-c.n.r.s. N°8638 Faculte Des
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Boutefnouchet Sabrina
Laboratoire De Pharmacognosie De L'universite Rene Descartes U.m.r.-c.n.r.s. N°8638 Faculte Des
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