3106-11-4Relevant articles and documents
Synthesis, biological activity screening and molecular modeling study of acylaminoacetamide derivatives
Coban, Gunes,Kose, Fadime Aydin,Kirmizibayrak, Petek Ballar,Pabuccuoglu, Varol
, p. 3710 - 3729 (2015/09/07)
In this study, non-rigid analogs of thalidomide have been designed in order to develop potentially active, more effective and safer lead molecules for disorders caused or contributed by inflammation. Five different series of acylaminoacetamide compounds were synthesized, and the biological inhibitory potency of the title compounds has been determined by evaluating their effects on COX-2 isoenzyme expression and PGE2 production in A549 (human lung adenocarcinoma) cell lines. Among the studied series, N-[2-(isopropylamino)-2-oxoethyl]isonicotinamide is the most active inhibitory compound on COX-2 isoenzyme expression, and N-[2-oxo-2-(pyrolydine-1-yl)etyl]isonicotinamide is the most active inhibitory compound on the biosynthesis of PGE2. Molecular docking studies and molecular dynamics simulations were also applied to investigate non-covalent interactions of the most active compounds inside the active side of the crystal structure of murine cyclooxygenase 2 (mCOX-2) isoenzyme.
Synthesis and anticonvulsant activity of some N-(benzoyl)glycinanilide derivatives
Soyer, Zeynep,Akgul, Ozlem,Tarikogullari, Ayse H.,Calis, Unsal
, p. 4708 - 4714 (2013/09/23)
Glycine is a major inhibitory neurotransmitter and recent studies have shown that certain lipophilic glycine derivatives demonstrate anticonvulsant activity in animal epilepsy models. On the other hand, anilide is another fruitful structure for designing potential anticonvulsant agents. Ameltolide, ralitoline and some phthalimide derivatives are the examples of anilide analogs with potent anticonvulsant activity. In this study, two key structural pharmacophores were combined and a series of N-benzoylglycinanilide derivatives were designed. Their anticonvulsant activities evaluated against maximal electroshock (MES) and subcutaneous metrazole seizure tests, whereas their neurotoxicity was examined by rotarod test. The preliminary screening results indicated that majority of the compounds were effective in the MES test. None of the compounds showed neurotoxicity according to the rotarod test at studied doses. The most active compound in the series is N-(2-((4-methoxyphenyl)amino)- 2-oxoethyl)benzamide (compound 8) which bearing 4-methoxy substituent on the N-phenyl ring.
A study of fragmentation of protonated amides of some acylated amino acids by tandem mass spectrometry: Observation of an unusual nitrilium ion
Talaty, Erach R.,Young, Sarah M.,Dain, Ryan P.,Van Stipdonk, Michael J.
experimental part, p. 1119 - 1129 (2012/03/26)
A tandem mass spectrometric study of a series of secondary amides of acetylglycine and hippuric acid utilizing electrospray ionization (ESI) was conducted. Among the fragment ions observed was an unusual one, which we have determined to be a nitrilium ion
Base catalysed methanolysis of 4-anilinomethylene-2-phenyl-2-oxazolin-5-one: Unexpected formation of N-benzoylaminoacetanilide
Singh,Singh,Singh
, p. 390 - 392 (2007/10/03)
The reaction of 4-anilinomethylene-2-phenyl-2-oxazolin-5-one 1 with 3.0 equivalents of sodium methoxide in methanol affords N-benzoylaminoacetanilide 3. Further, methyl 3-anilino-2-benzoylaminopropenoate 2 also affords product 3, when treated with sodium methoxide in methanol at reflux temperature. A plausible mechanism for this conversion has been proposed.
A novel rearrangement of 2-amino-3-phenacyl-1,3,4-oxadiazolium halides with hydroxylamine
Koeckritz,Hetzheim,Radeglia
, p. 436 - 440 (2007/10/03)
The reaction of 2-amino-3-phenacyl-1,3,4-oxadiazolium bromides 1 with hydroxylamine at various pH values is investigated. The intermediate oximes 6 undergo both BECKMANN rearrangement to the semicarbazide derivatives 7 and BECKMANN fragmentation to the benzonitriles 9. The structure of the compounds 7 was elucidated by special decoupling techniques of the 13C-1H NMR. spectra. Johann Ambrosius Barth 1996.
Transformation of N-acylaminoacetanilides and N-benzoylglycine hydrazides into 4-(N,N-dimethylaminomethylene)-2-aryl-2-oxazolin-5-ones using Vilsmeier-Haack reagent and their reactions with nucleophiles
Singh, Kumar K.,Singh, Manoj K.,Singh, Radhey M.
, p. 1119 - 1122 (2007/10/02)
A convenient one-pot synthesis of 4-(N,N-dimethylaminomethylene)-2-aryl-2-oxazolin-5-ones (5a-e) has been reported from the reaction of N-acylaminoacetanilides (3a-1) and N-benzoylglycine hydrazides (4a,b) with Vilsmeier-Haack reagent.Compound 5a undergoe
Synthesis of 1H-Imidazoles by the Simple Ring Transformation of 5-Acylaminouracils and 5-Acylaminopyrimidin-4(3H)-ones
Matsuura, Izumi,Ueda, Taisei,Murakami, Nobutoshi,Nagai, Shin-ichi,Sakakibara, Jinsaku
, p. 2821 - 2826 (2007/10/02)
1,2-Disubstituted 4-alkylcarbamoyl-5-methyl-1H-imidazoles and 2-substituted 5-methyl-4-phenylcarbamoyl-1H-imidazoles were synthesized from 5-acylamino-6-methyluracils and 5-acylamino-6-methyl-3-phenylpyrimidin-4(3H)-ones by treatment with sodium hydroxide in ethanol.In the case of 5-acylaminopyrimidinones which possess an olefinic group in the acylamino group, 2-ethoxyethyl (or 2-ethoxypropyl)-5-methyl-4-phenylcarbamoyl-1H-imidazoles were prepared as major products and the corresponding 2-alkenyl-1H-imidazoles were only minor products.Compounds which contain an aryl function in their acylamino group gave glycine anilides as byproducts.
