21101-63-3Relevant articles and documents
New potent antihyperglycemic agents in db/db mice: Synthesis and structure-activity relationship studies of (4-substituted benzyl)(trifluoromethyl)pyrazoles and -pyrazolones
Kees, Kenneth L.,Fitzgerald Jr., John J.,Steiner, Kurt E.,Mattes, James F.,Mihan, Brenda,Tosi, Theresa,Mondoro, Diane,McCaleb, Michael L.
, p. 3920 - 3928 (2007/10/03)
The synthesis, structure-activity relationship (SAR) studies, and antidiabetic characterization of 1,2-dihydro-4-[[4- (methylthio)phenyl]methyl]-5-(trifluoromethyl)-3H-pyrazol-3-one (as the hydroxy tautomer; WAY-123783, 4) are described. Substitution of 4-methylthio, methylsulfinyl, or ethyl to a benzyl group at C4, in combination with trifluoromethyl at C5 of pyrazol-3-one, generated potent antihyperglycemic agents in obese, diabetic db/db mice (16-30% reduction in plasma glucose at 2 mg/kg). The antihyperglycemic effect was associated with a robust glucosuria (>8 g/dL) observed in nondiabetic mice. Chemical trapping of four of the seven possible tautomeric forms of the heterocycle by mono- and dialkylation at the acidic hydrogens provided several additional potent analogs (39-43% reduction at 5 mg/kg) of the lead 4 as well as a dialkylated pair of regioisomers that showed separation of the associated glucosuric effect produced by all of the active analogs in normal mice. Further pharmacological characterization of the lead WAY-123783 (ED50 = 9.85 mg/kg, po in db/db mice), in oral and subcutaneous glucose tolerance tests, indicated that unlike the renal and intestinal glucose absorption inhibitor phlorizin, pyrazolone 4 does not effectively block intestinal glucose absorption. SAR and additional pharmacological data reported herein suggest that WAY-123783 represents a new class of potent antihyperglycemic agents which correct hyperglycemia by selective inhibition of renal tubular glucose reabsorption.
Heterocyclic pesticidal compounds
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, (2008/06/13)
Compounds of the formula (I) STR1 which contain between 10 and 27 carbon atoms, and wherein m and n are independently selected from 0, 1 and 2; R2a is hydrogen, methyl, or ethyl; R2b is acetylene or contains between 3 and 18 carbon atoms and is a group R7, wherein R7 is a C1-13 non-aromatic hydrocarbyl group, optionally substituted by a cyano or C1-4 carbalkoxy group and/or by one or two hydroxy groups and/or by one to five halo atoms which are the same or different and/or by one to three groups R8 which are the same or different and each contain one to four hetero atoms, which are the same or different and are chosen from oxygen, sulphur, nitrogen and silicon, 1 to 10 carbon atoms and optionally 1 to 6 fluoro or chloro atoms or R2b is a 6-membered aromatic ring substituted by cyano and/or by one to three groups R8 and/or by a group --C CH, --C C-R7 or C C-halo and/or by one to five halo atoms and/or by one to three C1-4 haloalkyl groups wherein R7 and R8 are as hereinbefore defined; R4 and R6 are the same or different and are chosen from hydrogen, methyl, trifluoromethyl or cyano; and R5 is hydrogen or methyl provided that R2b is not propyl or butyl are described which have pesticidal activity, particularly against arthropod pests. Pesticidal formulations containing the compounds of the formula (I), their use in the control of pests and method for their preparation are also disclosed.
Process for treating hyperglycemia using trifluoromethyl substituted 3H-pyrazol-3-ones
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, (2008/06/13)
The compound of the formula: STR1 in which the dotted lines represent two sites of unsaturation appropriately located based on the identity of R2, R3 and R4 and, R1 is alkyl, perfluoroalkyl, alkoxy, perfluoroalk
FLUORINE-CONTAINING AMINO ACIDS. VII. POLYFLUOROALKOXY AND POLYFLUOROMETHYLTHIO DERIVATIVES OF PHENYLALANINE
Kolycheva, M. T.,Yagupol'skii, Yu. L.,Gerus, I. I.,Godunova, L. F.,Kukhar, V. P.
, p. 1174 - 1179 (2007/10/02)
The reaction of polyfluoroalkoxy- and polyfluoromethylthio-substituted benzyl bromides with N-formylaminomalonic ester, followed by decarboxylation and alkaline hydrolysis, gave the corresponding derivatives of phenylalanine with fluorine-containing subst
M-phenoxybenzyl and α-cyano-M-phenoxybenzyl esters of 2-haloalkyl (oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids
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, (2008/06/13)
The invention is m-phenoxybenzyl esters of 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful insecticidal and acaricidal agents.
2-Haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)-phenylalkanoic acids
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, (2008/06/13)
The invention is 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful intermediates in the preparation of insecticides of m-phenoxybenzyl and α-cyano-m-phenoxybenzyl esters.
