- Discovery, synthesis, and evaluation of N-substituted amino-2(5H)- oxazolones as novel insecticides activating nicotinic acetylcholine receptors
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N-Substituted amino-2(5H)-oxazolones A are a novel class of insecticides acting as nicotinic acetylcholine receptor (nAChR) agonists and show potent activity against hemipteran insect species. Here we report the discovery and preparation of this class of chemistry. Our efforts in SAR elucidation, biological activity evaluation, as well as mode-of-action studies are also presented.
- Zhang, Wenming,Barry, James D.,Cordova, Daniel,McCann, Stephen F.,Benner, Eric A.,Hughes, Kenneth A.
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- MODIFIED COMPOUND OF ANDROGRAPHOLIDE
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The present disclosure discloses a modified compound of andrographolide, and particularly discloses a compound shown in formula (I) and (II) or a pharmaceutically acceptable salt thereof.
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Paragraph 0557-0559
(2019/01/04)
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- Structure Property Relationships of Carboxylic Acid Isosteres
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The replacement of a carboxylic acid with a surrogate structure, or (bio)-isostere, is a classical strategy in medicinal chemistry. The general underlying principle is that by maintaining the features of the carboxylic acid critical for biological activity, but appropriately modifying the physicochemical properties, improved analogs may result. In this context, a systematic assessment of the physicochemical properties of carboxylic acid isosteres would be desirable to enable more informed decisions of potential replacements to be used for analog design. Herein we report the structure-property relationships (SPR) of 35 phenylpropionic acid derivatives, in which the carboxylic acid moiety is replaced with a series of known isosteres. The data set generated provides an assessment of the relative impact on the physicochemical properties that these replacements may have compared to the carboxylic acid analog. As such, this study presents a framework for how to rationally apply isosteric replacements of the carboxylic acid functional group.
- Lassalas, Pierrik,Gay, Bryant,Lasfargeas, Caroline,James, Michael J.,Tran, Van,Vijayendran, Krishna G.,Brunden, Kurt R.,Kozlowski, Marisa C.,Thomas, Craig J.,Smith, Amos B.,Huryn, Donna M.,Ballatore, Carlo
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p. 3183 - 3203
(2016/05/19)
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- OXAZOLO[5,4-C]QUINOLIN-2-ONE COMPOUNDS AS BROMODOMAIN INHIBITORS
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The present invention relates to compounds useful as bromodomain inhibitors. The invention also provides pharmaceutically acceptable compositions comprising compounds of the present invention and methods of using said compounds and compositions in the treatment of various diseases and disorders.
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Paragraph 00227
(2014/10/04)
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- Dihydroindolone compounds, a process for their preparation and pharmaceutical compositions containing them
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Compounds of formula (I): wherein: m and n represent 1 or 2,A represents a pyrrolyl group,X represents a C(O), S(O) or SO2 group,R1 and R2 represent an alkyl group or, together with the nitrogen atom carrying them, form a heterocyclic group,R3 and R4, together with the atoms carrying them, form a heterocyclic group,R5 represents a hydrogen atom or an alkyl group,R6 represents a hydrogen atom or a halogen atom. Medicinal products containing the same which are useful in treating cancer.
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Page/Page column 9
(2011/02/26)
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- New heterocyclic inputs for the povarov multicomponent reaction
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Oxa-, thia- and imidazolones are reactive inputs as electron-rich olefin components in Povarov reactions. On interaction with anilines and aldehydes, these substrates afford the corresponding multicomponent adducts in a regioselective manner. Intramolecular processes are also explored. Post-condensation oxidation provides convenient access to a variety of fused quinoline derivatives. Georg Thieme Verlag Stuttgart ? New York.
- Vicente-Garcia, Esther,Ramon, Rosario,Lavilla, Rodolfo
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supporting information; experimental part
p. 2237 - 2246
(2011/09/15)
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- ARYLOXYALKYLCARBAMATE-TYPE DERIVATIVES, PREPARATION METHOD THEREOF AND USE OF SAME IN THERAPEUTICS
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The invention relates to a compound of formula (I): [image] Wherein m, n, X, Y, R1, R2, R3 and R4 are as defined herein. The invention also relates to the use of same in therapeutics.
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Page/Page column 6
(2008/06/13)
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- INDOLES HAVING ANTI-DIABETIC ACTIVITY
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Indoles of Formula (I) having -X-aryl-(CH2)x#191-oxazolidinedione and -X-heteroaryl-(CH2)X-oxazolidinedione substituents on the N atom of the indole ring, where x is 0 or 1, and -X-is a bond or -CH2-, and their thiazolidinedione analogs, are PPAR gamma agonists or partial agonists and are useful in the treatment and control of type II diabetes, including hyperglycemia, dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obesity that are often associated with type 2 diabetes.
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Page/Page column 41
(2008/06/13)
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- Electrolytic partial fluorination of organic compounds. Part 78: Regioselective anodic fluorination of 2-oxazolidinones
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Various 2-oxazolidinones were galvanostatically electrooxidized in the presence of various fluoride salts. It was found that a fluorine atom was introduced to the α-position of the nitrogen atom of N-acyl- and N-alkoxycarbonyl-2-oxazolidinones to provide the corresponding α-fluorinated products in moderate to good yields. In the case of N-phenoxycarbonyl derivative, fluorination took place on the phenyl group selectively.
- Cao, Yi,Suzuki, Katsutoshi,Tajima, Toshiki,Fuchigami, Toshio
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p. 6854 - 6859
(2007/10/03)
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- Tetraethylammonium hydrogen carbonate in organic synthesis: Synthesis of oxazolidine-2,4-diones
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Oxazolidine-2,4-diones were synthesised by tetraethylammonium hydrogen (TEAHC) promoted carboxylation of secondary carboxamides bearing a leaving group at the α-position. Several oxazolidine-2,4-diones, including clinically used malidone, have been prepared in moderate to excellent yields as a results of a formal proton extraction-carboxylation- intramolecular S(N)2 one-pot sequence.
- Cesa, Stefania,Mucciante, Vittoria,Rossi, Leucio
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p. 193 - 200
(2007/10/03)
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- Electrochemical Studies on Haloamides. Part XII. Electrosynthesis of Oxazolidine-2,4-diones
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Electrogenerated bases promote the carboxylation of NH-protic carboxamides bearing a leaving group at the position 2 to give oxazolidine-2,4-diones.The process is believed to involve acid-base reaction with the substrate, carboxylation of its conjugate base to corresponding carbamate and ring-closure following intramolecular SN2 reaction.A variety of oxazolidine-2,4-diones, including clinically used trimethadione and malidone, have been prepared in high to excellent yield, which established the scope and generality of this new ring-forming process.
- Casadei, Maria Antonietta,Cesa, Stefania,Inesi, Achille
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p. 5891 - 5900
(2007/10/02)
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- Benzyloxazolidine-2,4-diones as potent hypoglycemic agents
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A series of benzyloxazolidine-2,4-diones, containing oxazole-based side chains, were found to lower blood glucose levels in the genetically obese ob/ob mouse. Incorporation of a benzofuran structural element in these compounds provides greatly enhanced in vivo potency. The syntheses and structure-activity relationships for this series are detailed.
- Dow,Bechle,Chou,Clark,Hulin,Stevenson
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p. 1538 - 1544
(2007/10/02)
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- Photo-oxidation of Oxazolidones and Hydantoins in the Presence of Benzophenone
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Irradiation in the presence of benzophenone and oxygen of nitrogen-containing heterocycles having an NCO group yields products arising out of regioselective oxidation α to the nitrogen atom.Direct irradiation (in the absence of benzophenone and oxygen) of 5-methyl- and 5,5-dimethyl-hydantoins yields allophanates.The first step of this reaction involves the homolysis of the C(4) - C(5) bond of the hydantoin.
- Gramain, Jean-Claude,Remuson, Roland
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p. 2341 - 2346
(2007/10/02)
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- Spiro-oxazolidindiones
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Novel spiro-oxazolidindiones useful as aldose reductase inhibitors and as therapeutic agents for the treatment of chronic diabetic complications are disclosed. Pharmaceutical compositions containing the novel compounds and a method of treating chronic diabetic complications are also disclosed.
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