- Soluble polymer-supported synthesis of 4-methyl coumarin on modified poly(ethylene glycol)s
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A simple liquid phase synthetic method for the preparation of 4-methyl coumarin on modified poly(ethylene glycol)s by using the von Pechmann reaction is described.
- Tocco, Graziella,Begala, Michela,Delogu, Giovanna,Meli, Gabriele,Picciau, Carmen,Podda, Gianni
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Read Online
- A Simple, Effective and Highly Selective Cleavage of 3-Methylbut-2-enyl (prenyl) Ethers Using p-Toluenesulfonic Acid
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A highly selective cleavage of prenyl ethers has been achieved in high yields using p-toluenesulfonic acid under extremely mild conditions. This method is compatible with a wide variety of functional groups such as methyl, benzyl, allyl ethers and benzyl, methyl, prenyl esters present in the molecules.
- Babu, K. Suresh,Raju, B. China,Srinivas,Rao, A. Sridhar,Kumar, S. Praveen,Rao, J. Madhusudana
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Read Online
- Evaluation of 2-(piperidine-1-yl)-ethyl (PIP) as a protecting group for phenols: Stability to ortho-lithiation conditions and boiling concentrated hydrobromic acid, orthogonality with most common protecting group classes, and deprotection via Cope elimination or by mild Lewis acids
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A new protecting group, 2-(piperidine-1-yl)-ethyl (PIP), was evaluated as a protecting group for phenols. The PIP group was stable to ortho-lithiation conditions and refluxing with concentrated hydrobromic acid. Deprotection was accomplished by two routes, oxidation to N-oxides followed by Cope elimination (CE) and subsequent hydrolysis or ozonolysis of the vinyl ether or one-step deprotection by BBr3?Me2S. The PIP group is orthogonal to the O-benzyl, O-acetyl, O-t-butyldiphenylsilyl, O-methyl, O-p-methoxybenzyl, O-allyl, O-tetrahydropyranyl and N-t-butoxy carbonyl groups. The CE step was systematically studied and was found to give higher yields when the reaction was performed in the presence of silylating agents.
- Norén, Rolf
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- Structure–activity relationships and docking studies of hydroxychavicol and its analogs as xanthine oxidase inhibitors
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Hydroxychavicol (HC), which is obtained from the leaves of Piper betle LINN. (Piperaceae), inhibits xanthine oxidase (XO) with an IC50 value of 16.7μM, making it more potent than the clinically used allopurinol (IC50=30.7μM). Herein, a structure–activity relationship analysis of the polar part analogs of HC was conducted and an inhibitor was discovered with a potency 13 times that of HC. Kinetic studies have revealed that HC and its active analog inhibit XO in an uncompetitive manner. The binding structure prediction of these inhibitor molecules to the XO complex with xanthine suggested that both compounds (HC and its analog) could simultaneously form hydrogen bonds with xanthine and XO.
- Nishiwaki, Keiji,Ohigashi, Kanae,Deguchi, Takahiro,Murata, Kazuya,Nakamura, Shinya,Matsuda, Hideaki,Nakanishi, Isao
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p. 741 - 747
(2018/07/05)
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- BROMODOMAIN INHIBITORS FOR TREATING DISEASE
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Disclosed herein are compounds and compositions useful in the treatment of bromodomain-containing protein-mediated diseases, such as cancer, having the structure of Formula I: Methods of inhibiting activity of a bromodomain-containing protein in a human or animal subject are also provided.
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Paragraph 0196
(2016/03/19)
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- Biomimetic Total Synthesis of Santalin Y
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A biomimetic total synthesis of santalin Y, a structurally complex but racemic natural product, is described. The key step is proposed to be a (3+2) cycloaddition of a benzylstyrene to a "vinylogous oxidopyrylium", which is followed by an intramolecular F
- Strych, Sebastian,Journot, Guillaume,Pemberton, Ryan P.,Wang, Selina C.,Tantillo, Dean J.,Trauner, Dirk
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supporting information
p. 5079 - 5083
(2015/04/27)
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- Oxidative cyclization of alkenoic acids promoted by AgOAc
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Alkenoic acids derived from salicylic acid and analogues undergo an unexpected oxidative cyclization process triggered by AgOAc leading to 4H-benzo[d][1,3]dioxin-4-ones. The process is affected by the substitution on the aryl and the allyl units.
- Carrillo-Arcos, Ulises A.,Rojas-Ocampo, Jonathan,Porcel, Susana
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supporting information
p. 479 - 483
(2016/01/09)
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- Dialkoxybenzene and dialkoxyallylbenzene feeding and oviposition deterrents against the cabbage looper, trichoplusia ni: Potential insect behavior control agents
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The antifeedant, oviposition deterrent, and toxic effects of individual dialkoxybenzene compounds/sets and of hydroxy- or alkoxy-substituted allylbenzenes, obtained through Claisen rearrangement of substituted allyloxybenzenes, were assessed against the cabbage looper, Trichoplusia ni, in laboratory bioassays. Most of the compounds/sets strongly deterred larval feeding, with some exhibiting mild toxic and oviposition deterrent effects as well. Some of the compounds/sets were more active than the commercial insect repellent, DEET (N,N-diethyl-m-toluamide), as both feeding and oviposition deterrents against the cabbage looper. On the basis of the obtained oviposition data a general hypothesis was proposed regarding the oviposition sites: one binding mode with the alkyl and allyl groups on the same side of the benzene ring resulted in deterrence, the other with alkyl and allyl groups on opposite sides of the benzene ring resulted in stimulation. The results suggest some structure-activity relationships useful in improving the efficacy of the compounds and designing new, nontoxic insect control agents for agriculture.
- Akhtar, Yasmin,Yu, Yang,Isman, Murray B.,Plettner, Erika
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scheme or table
p. 4983 - 4991
(2011/08/06)
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- Boron trichloride mediated regioselective Claisen rearrangement of resorcinol derivatives: Application to resorcinol carvonyl ethers
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Claisen rearrangement (CR) of resorcinol allyl ethers was examined. Although thermal CR gave low regioselectivity, the selectivity was much improved in the presence of a Lewis acid such as boron trichloride. This rearrangement was successfully applied to resorcinol carvonyl ethers for the regioselective introduction of a carvone unit into the resorcinol skeleton for the synthesis of phytoestrogenic miroestrols. Georg Thieme Verlag Stuttgart.
- Ito, Fumihiro,Fusegi, Keiko,Kumamoto, Takuya,Ishikawa, Tsutomu
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p. 1785 - 1796
(2008/02/12)
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- New approach to the synthesis of macrocyclic tetralactones via ring-closing metathesis using Grubbs' first-generation catalyst
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(Chemical Equation Presented) A facile and efficient route to synthesize macrocyclic tetralactones with different ring sizes having a wide variety of spacers is described. The application of ring-closing metathesis for the synthesis of macrocyclic tetralactones is demonstrated with many examples in excellent yield. The representative structure of macrocyclic tetralactones is characterized by X-ray crystallography.
- Muthusamy, Sengodagounder,Gnanaprakasam, Boopathy,Suresh, Eringathodi
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p. 1495 - 1498
(2007/10/03)
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- Mild and efficient deprotection of allyl ethers of phenols and hydroxycoumarins using a palladium on charcoal catalyst and ammonium formate
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An efficient procedure for the cleavage of allyl phenyl ethers and allyl coumarinyl ethers using a catalytic amount of 10% Pd/C in combination with ammonium formate is described. Allyl ethers of phenols are deprotected in preference to those of alcohols and this method is compatible with several reducible functional groups such as CHO, COCH3, CO2Et and NHCOCH3.
- Ganguly, Nemai C.,Dutta, Sanjoy,Datta, Mrityunjoy
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p. 5807 - 5810
(2007/10/03)
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- Facile construction of the benzofuran and chromene ring systems via Pd II-catalyzed oxidative cyclization
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(Chemical Equation Presented) We herein report the development of one-pot procedures for the conversion of allyl aryl ethers to 2-methylbenzofurans (via sequential Claisen rearrangement and oxidative cyclization) and for the conversion of aryl homoallyl e
- So, Won Youn,Jeong, Im Eom
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p. 3355 - 3358
(2007/10/03)
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- Optimization and metabolic stabilization of a class of nonsteroidal glucocorticoid modulators
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The optimization of a series of nonsteroidal glucocorticoid modulators is reported. Potent selective GR ligands that have improved metabolic stability were discovered typified by the subnanomolar acid 12 (GR binding IC 50=0.6nM).
- Link,Sorensen, Bryan K.,Patel, Jyoti,Arendsen, David,Li, Gaoquan,Swanson, Susan,Nguyen, Bach,Emery, Maurice,Grynfarb, Marlena,Goos-Nilsson, Annika
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p. 4169 - 4172
(2007/10/03)
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- Zinc-catalyzed Williamson ether synthesis in the absence of base
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A zinc-catalyzed Williamson ether synthesis is described with microwave heating in the presence of DMF or stirring in an oil-bath using THF as solvent and in the absence of base. Zinc powder was found to be a highly efficient catalyst for the synthesis of aromatic ethers using microwave heating in the presence of N,N-dimethylformamide as well as under stirring in an oil-bath using tetrahydrofuran as solvent without any inorganic base. This method can be used for selective mono-, di- or tri-O-alkylations.
- Paul, Satya,Gupta, Monika
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p. 8825 - 8829
(2007/10/03)
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- The desymmetrisation of resorcinol: The synthesis of resorcinol monoalkyl ethers
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The desymmetrisation of resorcinol to give 3-alkoxyresorcinol derivatives can be achieved in excellent yields either from resorcinol monobenzoate and alcohols using Mitsunobu reactions followed by hydrolysis using a strong base or by using 3-iodophenylbenzyl ether as a resorcinol monobenzyl ether equivalent in reactions with alcohols catalysed by copper(I)-9,10-phenanthroline followed by ammonium formate-palladium catalysed hydrogenolysis.
- Boxhall, Jonathan Y.,Page, Philip C. Bulman,Chan, Yohan,Hayman, Colin M.,Heaney, Harry,McGrath, Matthew J.
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p. 997 - 1001
(2007/10/03)
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- Regioselectivity in aromatic Claisen rearrangements
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Theoretical calculations and the isomeric product composition for a series of eight meta-substituted allyl aryl ethers confirm the reliability of a new 1H NMR methodology used to predict aromatic Claisen regioselectivity from ground-state confo
- Gozzo, Fabio Cesar,Fernandes, Sergio Antonio,Rodrigues, Denise Cristina,Eberlin, Marcos Nogueira,Marsaioli, Anita Jocelyne
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p. 5493 - 5499
(2007/10/03)
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- GLUCOCORTICOID RECEPTOR MODULATORS
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Compounds of formula (I) or pharmaceutically acceptable salts thereof are novel glucocorticoid receptor modulators and are useful for treating type II diabetes in a mammal.
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- Novel synthesis of monoethers of hydroquinone and resorcinol on soluble polymer-supports
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Monoethers of hydroquinone and resorcinol were easily prepared using PEG as soluble polymer-supports, monoprotection group and phase transfer catalyst with good yields and high selectivity of functionlization in homogenous solution.
- Yang, Guichun,Chen, Zuxing,Zhang, Zhaojun,Qiu, Xiaoling
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p. 3637 - 3642
(2007/10/03)
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- Mechanistic Aspects and Synthetic Applications of the Electrochemical and Iodobenzene Bis(trifluoroacetate) Oxidative 1,3-Cycloadditions of Phenols and Electron-Rich Styrene Derivatives
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Anodic oxidation of p-methoxy-substituted phenols and electron-rich styrene or propenylbenzene derivatives affords in good yield trans-dihydrobenzofurans derived from a formal 1,3-oxidative cycloaddition of the phenol to the styrene derivative.The yield o
- Gates, Bradley D.,Dalidowicz, Peter,Tebben, Andrew,Wang, Shaopeng,Swenton, John S.
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p. 2135 - 2143
(2007/10/02)
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- SUBSTITUTED 2,3,3A,6-TETRAHYDRO-6-OXOBENZOFURAN DERIVATIVE USEFUL AS PAF ANTAGONIST
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Substituted 2,3,3a,6-tetrahydro-6-oxobenzofuran derivatives have been prepared. These neolignans are found to have potent and specific PAF (Platelet-Activating-Factor) antagonistic activities and thereby useful in the treatment of various diseases or diso
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- Structure-Activity Relationships of Kadsurenone Analogues
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Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol.Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 * 10-7 M, which is about 50percent of the activity of the natural product (IC50 = 1 * 10-7 M).The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.
- Ponpipom, Mitree M.,Bugianesi, Robert L.,Brooker, David R.,Yue, Bao-Zhen,Hwang, San-Bao,Shen, Tsung-Ying
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p. 136 - 142
(2007/10/02)
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- TOTAL SYNTHESIS OF KADSURENONE AND ITS ANALOGS
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Kadsurenone, a specific receptor antagonist of platelet-activating factor and a natural product isolated from Piper futokadsura was prepared in three steps from 3,4-dimethoxycinnamyl alcohol and allyloxyphenol via rac-(2S,3S)-5-allyl-6-hydroxy-2-(3,4-dime
- Ponpipom, M. M.,Yue, B. Z.,Bugianesi, R. L.,Brooker, D. R.,Chang, M. N.,Shen, T. Y.
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p. 309 - 312
(2007/10/02)
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