- Discovery of a novel series of peroxisome proliferator-activated receptor α/γ dual agonists for the treatment of type 2 diabetes and dyslipidemia
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A series of 2-aryloxy-2-methyl-propionic acid compounds and related analogues were designed, synthesized, and evaluated for their PPAR agonist activities. 2-[(5,7-Dipropyl-3-trifluoromethyl)-benzisoxazol-6-yloxy]-2- methylpropionic acid (4) was identified
- Liu, Kun,Xu, Libo,Berger, Joel P.,MacNaul, Karen L.,Zhou, Gauchao,Doebber, Thomas W.,Forrest, Michael J.,Moller, David E.,Jones, A. Brian
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- Novel synthesis of medium-sized oxa-heterocycles by palladium-catalyzed intramolecular Heck reaction
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An efficient and high yielding method for the synthesis of eight-membered heterocyclic skeletons has been developed via palladium-catalyzed intramolecular Heck reaction.
- Majumdar,Chattopadhyay,Ray
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- An expedient synthesis of bis-fused benzofuran and a two-directional ring- closing metathesis for the synthesis of bisbenzoxepines and bisbenzoxocines
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Synthesis of bis-fused benzofuran derivatives by the implementation of palladium-mediated intramolecular cyclization is described. To our knowledge, this is the first report of the synthesis of bis-fused benzofuran by this protocol. Bisbenzoxepine and bis
- Majumdar, Krishna C.,Chattopadhyay, Buddhadeb,Chakravorty, Santanu
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- An easy and efficient access to bis-allyloxy-arenes
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Bis-allyloxy-arenes were prepared in very good yields by reaction of the bis-hydroxy-arene on the appropriate allyl carbonate at room temperature in the presence of a palladium(0) catalyst.
- Kolodziuk,Kryczka,Lhoste,Porwanski,Sinou,Zawisza
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- Preparation of 1,3-bis(allyloxy)benzene under a new multi-site phase-transfer catalyst combined with ultrasonication - A kinetic study
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In the present work, kinetics of synthesis of 1,3-bis(allyloxy)benzene was successfully carried out by O-allylation of resorcinol with allyl bromide using aqueous potassium hydroxide and catalyzed by a new multi-site phase-transfer catalyst viz., 1,3,5,7-tetrabenzylhexamethylenetetraammonium tetrachloride, MPTC under ultrasonic (40 kHz, 300 W) assisted organic solvent condition. The pseudo first-order kinetic equation was applied to describe the overall reaction. Under ultrasound irradiation (40 kHz, 300 W) in a batch reactor, it shows that the overall reaction rate can be greatly enhanced to seven fold faster with ultrasound irradiation than without ultrasound. The present study provides a method to synthesize ethers by ultrasound assisted liquid-liquid phase-transfer catalysis condition.
- Selvaraj, Varathan,Rajendran, Venugopal
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- Design and discovery of 2-oxochromene derivatives as liver X receptor β-selective agonists
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In an attempt to molecularly design liver X receptor (LXR) β-selective agonists, we discovered that the combination of the 2-oxochromene moiety (head) and the imidazoline-2,4-dione moiety (tail) plays an important role in the expression potency and select
- Matsuda, Takayuki,Okuda, Ayumu,Watanabe, Yuichiro,Miura, Tohru,Ozawa, Hidefumi,Tosaka, Ayako,Yamazaki, Koichi,Yamaguchi, Yuki,Kurobuchi, Sayaka,Koura, Minoru,Shibuya, Kimiyuki
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supporting information
p. 1274 - 1278
(2015/03/14)
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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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- METHODS AND COMPOSITIONS FOR CONTROL OF GYPSY MOTHS, Lymanria dispar
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The invention provides in part dialkoxybenzene and eugenol compounds for controlling infestation by a Lymantria dispar, and methods thereof. The compounds include a compound of Formula I: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; R2 may be at positions 2, 3 or 4 and may be H, methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; and R3 may be optionally present at positions 2, 3 and 4, and is allyl; with the provisos that when R2 is at position 2, R3 if present is at position 3, or when R2 is at to position 3, R3 if present is at positions 2 or 4, or when R2 is at position 4, R3 if present is at position 2; or of Formula II: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl (3-methylbutyl) or allyl; or mixtures thereof.
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Page/Page column 11
(2010/08/07)
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- METHODS AND COMPOSITIONS FOR CONTROL OF CABBAGE LOOPER, Trichoplusia ni
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The invention provides in part dialkoxybenzene compounds for controlling infestation by a Trichoplusia ni, and methods thereof. The compounds include a compound of Formula I: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl(3-methylbutyl) or allyl; R2 may be at positions 2, 3 or 4 and may be H, methyl, ethyl, propyl, n-butyl, isopentyl(3-methylbutyl) or allyl; and R3 may be optionally present at positions 2, 3 and 4, and is allyl; except that when R2 is at position 2, R3 if present is at position 3, and when R2 is at position 3, R3 if present is at positions 2 or 4, and when R2 is at position 4, R3 if present is at position 2, and when R2 is at position 4 and R3, if present, has reacted with an OH group at position 1 in a Markovnikov sense, then R3 becomes R4, a dihydrofuran.
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Page/Page column 11
(2010/07/04)
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- Effect of ortho-SR groups on O-H bond strength and H-atom donating ability of phenols: A possible role for the tyr-cys link in galactose oxidase active site?
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Rotation about the Ar-S bond in ortho-(alkylthio)phenols strongly affects the bond dissociation enthalpy (BDE) and the reactivity of the OH group. Newly synthesized sulfur containing heterocycles 3 and 4, where the -SR group is almost coplanar with the phenolic ring, are characterized by unusually low BDE(O-H) values (79.6 and 79.2 kcal/mol, respectively) and by much higher reactivities toward peroxyl radicals than the ortho-methylthio derivative 1 (82.0 kcal/mol). The importance of the intramolecular hydrogen bond (IHB) in determining the BDE(O-H) was demonstrated by FT-IR experiments, which showed that in heterocycles 3 and 4 the IHB between the phenolic OH group and the S atom is much weaker than that present in 1. Since the IHB can be formed only if the -SR group adopts an out-of-plane geometry, this interaction is possible only in the methylthio derivative 1 and not in 3 and 4. The additive contribution to the phenolic BDE(O-H) of the -SR substituent therefore varies from -3.1 to +2.8 kcal/mol for the in-plane and out-of-plane conformations, respectively. These results may be relevant to understanding the role of the tyrosine-cysteine link in the active site of galactose oxidase, an important enzyme that catalyzes the two-electron aerobic oxidation of primary alcohols to aldehydes. The switching of the ortho -SR substituent between perpendicular and planar conformations may account for the catalytic efficiency of this enzyme.
- Amorati, Riccardo,Catarzi, Francesca,Menichetti, Stefano,Pedulli, Gian Franco,Viglianisi, Caterina
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p. 237 - 244
(2008/09/21)
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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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- 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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- Aryloxyacetic acids for diabetes and lipid disorders
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A class of aryloxyacetic acids comprises compounds that are potent agonists of PPAR alpha and/or gamma, and are therefore useful in the treatment, control or prevention of non-insulin dependent diabetes mellitus (NIDDM), hyperglycemia, dyslipidemia, hyper
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- Aryloxyacetic acids for diabetes and lipid disorders
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A class of aryloxyacetic acids comprises compounds that are potent agonists of PPAR alpha and/or gamma, and are therefore useful in the treatment, control or prevention of non-insulin dependent diabetes mellitus (NIDDM), hyperglycemia, dyslipidemia, hyper
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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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