41994-91-6Relevant academic research and scientific papers
Formamide as an ammonia synthon in amination of acid chlorides
Srinivasan,Manisankar
experimental part, p. 3538 - 3543 (2011/02/22)
The use of formamide as a convenient source of ammonia has been explored for the direct transformation of acid chlorides to primary amides. Various aliphatic, alicyclic aromatic, and heterocyclic acid chlorides are converted to the corresponding carboxamides in good yields (75-94%). Copyright Taylor & Francis Group, LLC.
Evaluation and biological properties of reactive ligands for the mapping of the glycine site on the N-methyl-D-aspartate (NMDA) receptor
Kreimeyer, Annett,Laube, Bodo,Sturgess, Mike,Goeldner, Maurice,Foucaud, Bernard
, p. 4394 - 4404 (2007/10/03)
The glycine-binding site of the N-methyl-D-aspartate (NMDA) receptor, given its potential as pharmacological target, has been thoroughly studied by structure-activity relationships, which has made possible its description in terms of spatial limits and interactions of various types. A structural model, based on mutational analysis and sequence alignments, has been proposed. Yet, the amino acid residues responsible for the interactions with the ligand have not been unambiguously characterized. To evidence nucleophilic pocket-lining residues, we have designed and synthesized reactive glycine-site ligands derived from 3-substituted 4-hydroxy-quinolin- 2(1H)-ones by introducing various electrophilic groups at different positions of the molecule. These ligands were found to have high affinity at the glycine site and to be functional antagonists by inhibiting glycine/glutamate-induced currents in transfected oocytes. The correlation between their potency and their substitution pattern was strictly consistent with previously established structure-activity relationships. Most ligands displayed intrinsic reactivity toward cysteine, but none inactivated wild- type receptors. This is consistent with the model since it indicates the absence of exposed cysteine in the glycine-binding site. A strategy of cysteine incorporation by point mutations at selected polypeptide positions will create unambiguously localized targets for our reactive probes.
3H-azepines and related systems. Part 5. Photo-induced ring expansions of o-azidobenzonitriles to 3-cyano- and 7-cyano-3H-azepin-2(1H)-ones
Lamara,Redhouse,Smalley,Thompson
, p. 5515 - 5525 (2007/10/02)
Unlike other aryl azides bearing electron-withdrawing ortho-substituents, o-azidobenzonitriles on photolysis in aqueous-tetrahydrofuran yield mixtures of the expected 3-cyano- and the unexpected 7-cyano-3H-azepin-2(1H)-ones. In one instance ring contraction to a 2-azabicyclo[3.2.0]hept-6-ene-3-one is noted. X-ray crystallographic data for 7-cyano- and 4-chloro-7-cyano-3H-azepin-2-one, and for the azabicycloheptenone, are presented.
Substituted quinazolines as angiotensin II antagonists
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, (2008/06/13)
There are disclosed compounds of the general formula I: STR1 wherein A is --CR7 =CR8 --; Z is --CR7 =CR8 --; X is H, NR 9 R10, OR11, CN, F, Cl, I, Br, perfluoroalkyl, alkyl,alkoxy, alkyl-OH, alkoxyalkyl, --(CH2)n CO2 R11,--(CH2)n CONR9 R10 ; Y is NR13,NR13 CR12 R14, CR12 R14 NR13 ; R1 is 5-tetrazolyl, CO2 R11,SO3 H, NHSO2 CH3, NHSO2 CF3 ; R2,R3,R4,R7 R8 is H, alkyl, alkoxy, alkoxyalkyl, alkyl-OH, perfluoroalkyl, aralkyl, CN, NO2, SO2 R13, --(CH2)n CO2 R11,--(CH2)n CONR9 R10, OR11,F,Cl,Br,I,NR9 R10 ; R5 is alkyl, alkoxy, alkoxyalkyl, alkyl-OH, perfluoroalkyl, aralkyl, H, --CN, NO2, SO2 R13,--(CH2)n CO2 R11, --(CH2)n CONR9 R10, --OH,OR11,F,Cl,Br,I,NR9 R10 ; R9,R10 is H, alkyl, alkoxyalkyl,alkyl-OH, perfluoroalkyl, aralkyl; R11 is H, alkyl, aralkyl, alkoxyalkyl; R12,R14 is H, alkyl, alkoxy, alkoxyalkyl, alkyl-OH, perfluoroalkyl, aralkyl, CN, NO2, SO2 R13, --(CH2)n CO2 R11, --(CH2)n CONR9 R10 ; R13 is H, OR11, alkyl, perfluoroalkyl, aralkyl, --(CH2)n CO2 R11,--(CH2)n CONR9 R10 ; wherein alkyl is defined as 1-8 carbons, branched or straight chain; perfluoroalkyl is defined as 1-6 carbons; aralkyl is defined as 7-12 carbons or 7-12 carbons substituted with fluorine, bromine or chlorine and the phamaceutically acceptable salts, solvates and hydrates thereof, which by virtue of their ability to antagonize angiotensin II are useful for the treatment of hypertension and congestive heart-failure. The compounds are also useful for reducing lipid levels in the blood plasma and are thus useful for treating hyperlipidemia and hypercholesterolemia. Also disclosed are processes for the production of said compounds and pharmaceutical compositions containing said compounds.
1,2,3-Benzotriazin-4-ones and related systems. Part II. Thermolytic decomposition of substituted 1,2,3-benzotriazin-4-ones and isatoic anhydrides
Archer, John G.,Barker, Alan J.,Smalley, Robert K.
, p. 1169 - 1173 (2007/10/06)
Several nuclear-substituted 1,2,3-benzotriazin-4-ones have been thermolysed in an inert solvent. In each case the major identifiable product proved to be a 2-(o-aminophenyl)-3,1-benzoxazin-4-one. Nuclear-substituted isatoic anhydrides on thermolysis behaved similarly.
