- Synthesis and Antiproliferative Activity of Natural and Non-Natural Polymethoxychalcones and Polymethoxyflavones
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Two series of polymethoxychalcones and polymethoxyflavones, including the natural products 2′-hydroxy-3,4,5,4′,6′-pentamethoxychalcone (8c), 5,6,7,8,3′,4′,5′-heptamethoxyflavone (6), 5,7,3′,4′,5′-pentamethoxyflavone (9c), 3-hydroxy-5,6,7,8,3′,4′,5′-heptam
- Vongdeth, Kingsadingthongkham,Han, Peipei,Li, Wei,Wang, Qiu-An
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- Rhodium-catalyzed cleavage reaction of aryl methyl ethers with thioesters
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A rhodium complex catalyzed the reaction of aryl methyl ethers and thioesters giving the corresponding aryl esters and methyl sulfides. S-(p-Chlorophenyl) p-(dimethylamino)benzothioate was used for the reaction of methyl aryl ethers with electron-withdrawing groups, and an S-(p-tolyl) derivative was used for those with electron-donating groups. Polymethoxybenzenes were converted to the esters in a regioselective manner.
- Arisawa, Mieko,Nihei, Yuri,Suzuki, Takaaki,Yamaguchi, Masahiko
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supporting information; experimental part
p. 855 - 857
(2012/03/26)
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- PET imaging of nobiletin based on a practical total synthesis
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A practical synthesis of nobiletin, a polymethoxylated citrus flavone, was accomplished by utilizing our novel flavone synthesis. Synthetic nobiletin was labelled by selective demethylation and rapid incorporation of 11C atom. Positron emission tomography images successfully visualized the brain distribution, which may provide therapeutic benefits in the treatment of Alzheimer's disease. The Royal Society of Chemistry.
- Asakawa, Tomohiro,Hiza, Aiki,Nakayama, Miho,Inai, Makoto,Oyama, Dai,Koide, Hiroyuki,Shimizu, Kosuke,Wakimoto, Toshiyuki,Harada, Norihiro,Tsukada, Hideo,Oku, Naoto,Kan, Toshiyuki
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p. 2868 - 2870
(2011/04/22)
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- Miscrowave-assisted efficient synthesis of polymethoxyacetophenones and natural polymethoxyflavones, and thier inhibitory effects on melanogenesis
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Microwave, assisted Friedel-Crafts acetylation of polymethoxybenzenes with acetic anhydride in the presence of In(CF3SO3)3 under solvent-free conditions was achieved rapidly to give polymethoxyacetophenones in high yields. Microwave-assisted benzoylation of 2'-hydroxypolymethoxyacetophenones with polymethoxybenzoyl chlorides, followed by the rearrangement of the resulting benzoates and the final formation of natural polymethoxyflavones was achieved rapidly and efficiently. The polymethoxyflavones showed inhibitory effects on melanogenesis in human melanoma cells.
- Tsukayama, Masao,Kusunoki, Eiji,Hossain, Mohammad M.,Kawamura, Yasuhiko,Hayashi, Shinji
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p. 1589 - 1600
(2008/09/17)
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- The Baeyer-Villiger Oxidation of Aromatic Aldehydes and Ketones with Hydrogen Peroxide Catalyzed by Selenium Compounds
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A series of organoselenium compounds was investigated as activators of hydrogen peroxide in the Baeyer-Villiger oxidation.As a result, a convenient and cheap method for transformation of aromatic aldehydes, having polycondensed ring systems or electron-donating substituents, and polymethoxy derivatives of acetophenone, into phenols was elaborated.This method utilizes hydrogen peroxide activated by areneseleninic acids, as oxidizing agent.
- Syper, Ludwik
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p. 167 - 172
(2007/10/02)
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- An Improved Synthesis of 1,4-Benzo- and 1,4-Naphthoquinones Bearing Active Substituents
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The synthesis of 1,4-benzoquinones and 1,4-naphthoquinones 3a-j carrying substituents such as methoxyl, allyl or oxiranyl was substantially improved.The 1-methoxy-4-methoxymethyloxy 2a-d, g-k or 1,4-bis(methoxymethyloxy) derivatives 2e-f were used, as a substrates instead of 1,4-dimethoxy derivatives 1a-j hitherto used and they were oxidized with silver(II) dipicolinate.Among numerous examples, the synthesis of a new analog of ubiquinone 3d with the oxiranyl substituent, being a new bioactivated alkylating agent, is reported.
- Syper, Ludwik,Kloc, Krystian,Mlochowski, Jacek
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p. 808 - 822
(2007/10/02)
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