- Ethynylbenzenoid metabolites of Antrodia camphorata: Synthesis and inhibition of TNF expression
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An improved synthesis of the anti-inflammatory natural product antrocamphin A (2), involving a key Castro-Stephens reaction, is presented, along with the first total synthesis of its congener antrocamphin B (3). Approaches towards the more complex co-meta
- Buccini, Marco,Punch, Kathryn A.,Kaskow, Belinda,Flematti, Gavin R.,Skelton, Brian W.,Abraham, Lawrence J.,Piggott, Matthew J.
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p. 1100 - 1113
(2014/02/14)
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- First total synthesis of antrocamphin A and its analogs as anti-inflammatory and anti-platelet aggregation agents
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Naturally occurring antrocamphin A (1) is a potent anti-inflammatory compound from the edible fungus Antrodia camphorata (Taiwanofungus camphoratus), whose wild fruiting body is used as a valuable folk medicine in Taiwan. This study is the first total syn
- Lee, Chia-Lin,Huang, Chi-Huan,Wang, Hui-Chun,Chuang, Da-Wei,Wu, Ming-Jung,Wang, Sheng-Yang,Hwang, Tsong-Long,Wu, Chin-Chung,Chen, Yeh-Long,Chang, Fang-Rong,Wu, Yang-Chang
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supporting information; experimental part
p. 70 - 73
(2011/02/23)
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- Synthesis of the proposed structure of queenslandon
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The proposed structure of the benzolactone queenslandon (6) was synthesized utilizing a triol containing building block prepared from d-ribose. While a ring-closing metathesis approach did not lead to the macrocycle, alkylation of a benzyl(phenyl)selane, elimination to generate the styrene double bond, followed by Mitsunobu macrolactonization proved to be successful. Spectral data suggest that the structure of queenslandon should be revised, probably to the C11 epimer.
- Navickas, Vaidotas,Maier, Martin E.
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supporting information; scheme or table
p. 94 - 101
(2010/03/03)
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- MACROCYCLIC COMPOUNDS USEFUL AS PHARMACEUTICALS
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The present invention provides compounds having formula (I), and additionally provides methods for the synthesis thereof and methods for the use thereof in the treatment of various disorders including inflammatory or autoimmune disorders, and disorders involving malignancy or increased angiogenesis, wherein R1 -R11, t, X, Y, Z, and n are as defined herein.
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Page/Page column 209-210
(2010/02/07)
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- DNA cleavage by Di- and trihydroxyalkylbenzenes. Characterization of products and the roles of O2, Cu(II), and alkali
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Several 5-alkyl-1,3-dihydroxybenzene (5-alkylresorcinol, 1) and 6-alkyl-1,2,4-trihydroxybenzene (2) derivatives were prepared and used to study the mechanism by which such compounds effect Cu(II)-dependent DNA strand scission. Comparison of the methyl, n-pentyl, n-undecyl, and n-hexadecyl derivatives in each structural series indicated that the efficiency of DNA cleavage increased with increasing length of the alkyl substituent. DNA cleavage by the 5-alkylresorcinols appears to involve initial oxygenation of the benzene nucleus, a process that occurs readily at alkaline pH in the presence of Cu2+ and O2. The resulting trihydroxylated benzenes mediate DNA cleavage in a reaction dependent on the presence of both Cu2+ and O2. The mechanism appears to involve reduction of Cu2+ by the trihydroxybenzene moiety in 2, with subsequent formation of reactive oxygen species. The ability of catalase and dimethyl sulfoxide to suppress DNA strand scission is consistent with the intermediacy of H2O2 and ?OH in the DNA strand scission process.
- Singh, Udai S.,Scannell, Ralph T.,An, Haoyun,Carter, Barbara J.,Hecht, Sidney M.
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p. 12691 - 12699
(2007/10/03)
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- Syntheses of Karwinaphthol B, 7-Methoxyeleutherin and Ventiloquinone E.
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Acylation of the aryl nitromethane (35) with (9) gave the enone (45), which underwent cyclization to the tricyclic system (50).Thermally induced aromatization to the naphthopyran (51) and oxidation gave ventiloquinone E (3).On selective demethylation this
- Cameron, Donald W.,Crosby, Ian T.,Feutrill, Geoffrey I.,Pietersz, Goeffrey A.
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p. 2003 - 2024
(2007/10/02)
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- A Synthesis of the Lichen Xanthone Thiomelin
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A total synthesis of thiomelin (2,4-dichloro-1,8-dihydroxy-5-methoxy-6-methyl-9H-xanthen-9-one) (1) has been achieved.
- Elix, John A.,Portelli, Victor J.
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p. 1773 - 1778
(2007/10/02)
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- AN INVESTIGATION OF THE BIOSYNTHESIS OF CITROMYCETIN IN PENICILLIUM FREQUENTANS USING (13)C- AND (14)C-LABELLED PRECURSORS
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Citromycetin (1) has been shown by (13)C n.m.r. to incorporate seven intact acetate units from -, -, and -acetates in accordance with a polyketide biosynthesis.The distribution of radioactivity following incorporation of malonate was consistent with the utilisation of two starter units.The following possible advanced precursors, labelled with (14)C, were not incorporated : 2,4-dihydroxy-6-methylbenzoic acid (14), 4,5,7-trihydroxyphthalide (16), and 4,7-dihydroxy-5-methylcoumarin (18).Two compounds, 2,4,5-trihydroxy-6-methylbenzoic acid (15) and triacetic acid lactone (17), were degraded to radiolabelled acetate prior to incorporation.
- Evans, Geoffrey E.,Staunton, James
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p. 755 - 762
(2007/10/02)
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- AN IMPROVED REDUCTIVE METHYLATION PROCEDURE FOR QUINONES
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The reductive methylation of quinones bearing electrone donating groups such as hydroxyl or alkoxyl groups proceeds in good yields.The improved conditions greatly extend the scope of this useful reaction.
- Kraus, George,Man, Tim On
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p. 1037 - 1042
(2007/10/02)
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- FORMAL TOTAL SYNTHESIS OF β-PIPITZOL
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(+/-)-O-methylperezone (1b) was obtained by selective oxidative demethylation of (+/-)-leucoperezone trimethyl ether (4a).Compound (4a) was prepared by condensation of 2,3,5-trimethoxytoluene (5e) with 6-methyl-5-heptene-2-one, followed by reductive removal of the tertiary alcohol.The aromatic precursor 5e was prepared in four steps from 2,3-dimethoxytoluene (5a) and, alternatively, in three steps from 5-bromoveratraldehyde (6a).Racemic 1b and 4a were directly compared with the optically active molecules prepared from natural R(-)-perezone (1a).
- Sanchez, Ignacio H.,Larraza, Maria Isabel,Basurto, Fernando,Yanez, Ricardo,Avila, Salvador,et al.
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p. 2355 - 2359
(2007/10/02)
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