5446-46-8Relevant academic research and scientific papers
Synthesis and preliminary anti-inflammatory and anti-bacterial evaluation of some diflunisal aza-analogs
Carta, Davide,Brun, Paola,Dal Pra, Matteo,Bernabè, Giulia,Castagliuolo, Ignazio,Ferlin, Maria Grazia
, p. 1017 - 1032 (2018/06/27)
Our aim was to identify new multi-target compounds endowed with both anti-inflammatory and anti-bacterial activities for treatment of human infections. Diflunisal, a nonsteroidal anti-inflammatory agent, has recently been repurposed for its anti-virulence properties against methicillin-resistant Staphylococcus aureus. Effective synthesis of some aza-analogs of the anti-inflammatory drug diflunisal was carried out following the route involving key oxazole intermediates to obtain o- and m-hydroxypyridinecarboxylic acid derivatives. The newly synthesized diflunisal aza-analogs did not exhibit cytotoxic activity up to 80 μM and some of them exhibited anti-inflammatory activities, decreasing the levels of pro-inflammatory cytokines and prostaglandins induced by bacterial lipopolysaccharide in human primary macrophages. Ten of the diflunisal aza-analogs were found to have interesting antibacterial activity, sensitizing S. aureus, Streptococcus pyogenes, Enterococcus faecium, and Pseudomonas aeruginosa to the antibacterial effects of beta-lactam antibiotics and protein synthesis inhibitors.
New efficient synthesis of 5-ethoxyoxazoles and oxazolo[3,2-c]quinazolines via aza-Wittig reaction
Huang, Nian-Yu,Nie, Yi-Bo,Ding, Ming-Wu
experimental part, p. 611 - 614 (2009/06/28)
5-Ethoxyoxazoles or 2-acylamino propanoates were synthesized by aza-Wittig reaction of iminophosphorane with acyl chloride in the presence of triethylamine. Reactions of 5-alkoxyoxazole with triphenyphosphine produced iminophosphoranes. A tandem aza-Wittig reaction of iminophosphorane with isocyanate or carbon disulfide generated oxazolo[3,2-c]quinazolines in satisfactory yields. Georg Thieme Verlag Stuttgart.
Amidoearbonylation of aldehydes utilizing cobalt oxide-supported gold nanoparticles as a heterogeneous catalyst
Hamasaki, Akiyuki,Liu, Xiaohao,Tokunaga, Makoto
scheme or table, p. 1292 - 1293 (2009/12/03)
Cobalt oxide-supported gold-nanoparticles-catalyzed transformation of aldehydes and their equivalents to N-acyl-α-arnino acids was achieved. The desired products were obtained in moderate to excellent yields under milder reaction conditions than previous reports employing octacarbonyldicobalt as a catalyst. Copyright
Radical Chain Reactions of α-Azido-β-keto Esters with Tributyltin Hydride. a Novel Entry to Amides and Lactams through Regiospecific Nitrogen Insertion
Benati, Luisa,Nanni, Daniele,Sangiorgi, Corrado,Spagnolo, Piero
, p. 7836 - 7841 (2007/10/03)
A variety of acyclic and carbocyclic α-azido-β-keto esters have been readily prepared from the parent dicarbonyl compounds, and their radical chain reactions with tributyltin hydride have been investigated. These reactions normally result in efficient production of alkoxycarbonyl-substituted amides and lactams and thence provide a new, useful method for regiospecific nitrogen insertion of keto ester compounds. The likely mechanism entails initial addition of tributylstannyl radical to the azido moiety to give a stannylaminyl radical, which readily undergoes intramolecular three-membered cyclization onto the ketone group to form an alkoxyl radical. The alkoxyl radical then undergoes regiospecific β-scission to form a stable ring-opened radical that is eventually reduced by tributyltin hydride to propagate the chain. With certain substrates, concomitant deazidation occurs to an important extent. This process, which is unusually observed in radical reactions of alkyl azides, is ascribed to addition of the stannyl radical to the terminal azido nitrogen; subsequent fragmentation of the ensuing 1,3-triazenyl adduct gives stannyl azide and a deazidated alkyl radical, resonance-stabilized by the adjacent carbonyl groups. The radical reactions of 2-azido-2-(ethoxycarbonyl)-1-tetralone with allyltributylstannane and allyltriphenylstannane have also been investigated with the (missed) aim to achieve nitrogen insertion and concomitant allylation.
Compounds having an aryltriazine structure
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, (2008/06/13)
A compound having an aryltriazine structure selected from those of formula (I): STR1 for which the meaning of the substituents Ar, R1, R5, R6, and R6 ' is given in the description. The compound of the invention is useful as medicinal product for disorders associated with a cholinergic dysfunction.
A New Synthesis of Peptides from Azides and Unactivated Carboxylic Acids
Zaloom, Jeffrey,Calandra, Michael,Roberts, David C.
, p. 2601 - 2603 (2007/10/02)
The title reaction, in which an azido compound is treated first with a tertiary phosphine, followed by warming in an inert solvent with a carboxylic acid, has been used to synthesize a number of small peptides and appears from mechanistic studies to proceed via a pentacoordinate phosphorus intermediate.
Steric Course of Ketopantoate Hydroxymethyltransferase in E. coli
Aberhart, D. John,Russell, David J.
, p. 4902 - 4906 (2007/10/02)
The conversion of α-ketoisovaleric acid (α-KIVA) to ketopantoate by the 5,10-methylenetetrahydrofolate-dependent enzyme ketopantoate hydroxymethyltransferase (KHMT) in E. coli has been shown to proceed in a retention mode at the β-position of α-KIVA. 5,10-methylenetetrahydrofolate formed in vivo by serine hydroxymethyltransferase (SHMT) from stereospecifically deuterated (3S-d1) serine was converted by KHMT into an ca. 3:1 ratio of deuterated ketopantoates with the 4S isomer predominating.The results indicate that KHMT and SHMT have the same overall steric course in E. coli.
