14304-68-8Relevant 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.
Alkyl halide-free heteroatom alkylation and epoxidation facilitated by a recyclable polymer-supported oxidant for the in-flow preparation of diazo compounds
Nicolle, Simon M.,Hayes, Christopher J.,Moody, Christopher J.
, p. 4576 - 4579 (2015/03/18)
Highly reactive metal carbenes, generated from simple ketones via diazo compounds, including diazoamides and -phosphonates, using a recyclable reagent inflow, are transient but versatile electrophiles for heteroatom alkylation reactions and for epoxide formation. The method produces no organic waste, with the only byproducts being water, KI and nitrogen, without the attendant hazards of isolation of intermediate diazo compounds.
Resolution of N-protected amino acid esters using whole cells of Candida parapsilosis ATCC 7330
Stella, Selvaraj,Chadha, Anju
experimental part, p. 457 - 460 (2010/06/21)
Whole cells of Candida parapsilosis ATCC 7330 were used for the resolution of N-acetyl amino acid esters. Excellent enantioselectivities (E = 40 to >500) were achieved for the resolution of N-protected protein and non-protein amino acid esters giving good yields (28-50%) and high enantiomeric excesses (up to >99%) for both enantiomers.
Improved Reagent for Electrophilic Amination of Stabilized Carbanions
Smulik, Jason A.,Vedejs, Edwin
, p. 4187 - 4190 (2007/10/03)
(Equation presented) Enolate amination using O-di(p-methoxyphenyl) phosphinylhydroxylamine 2 is reported. Reagent 2 reacts efficiently with stabilized sodium or potassium enolates derived from malonates, phenylacetates, and phenylacetonitriles and is sufficiently soluble for use in solution at -78°C.
Reaction of organolead triacetates with 4-ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one. The synthesis of α-aryl- and α-vinyl-N-acetylglycines and their ethyl esters and their enzymic resolution
Morgan, Jacqueline,Pinhey, John T.,Sherry, Christopher J.
, p. 613 - 619 (2007/10/03)
4-Ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one 7, which may be readily obtained from diethyl acetamidomalonate, undergoes high-yielding arylation and vinylation at the 4-position with organolead triacetates to give compounds which may be hydrolysed to give either the α-aryl- or α-vinyl-N-acetylglycine or the corresponding ethyl ester. The kinetic resolution of a number of these derivatives by enzymic hydrolysis of either the amide or ester function has been demonstrated.
