Oxazoles

Dietary and Microbial Oxazoles Induce Intestinal Inflammation by Modulating Aryl Hydrocarbon Receptor Responses

“…Oxazolone is administered in experimental models of colitis and contact sensitivity but is also widely used in industry and pharmaceuticals as a pharmacophore for the generation of synthetic compounds, suggesting it may act as a potential environmental trigger of inflammation in sensitive hosts (Turchi, 2008). We therefore sought to identify a library of structural mimetics of oxazolone and test whether these molecules behaved in a similar manner.…”

“…Based on these observations, we inquired whether oxazolone is representative of a broader class of environmental factors that may be involved in the pathogenesis of IBD and possess a conserved or shared substructure. Oxazolone, first synthesized in 1883 by Erlenmeyer and Plöchl (Plöchl, 1884; Erlenmeyer, 1893), has been widely utilized as a synthetic building block for compounds with a range of pharmacological properties (Turchi, 2008) and is also naturally abundant in diet as a component of many thermally processed foods, pesticides, and other environmental sources (Maga, 1978). In addition, microbes are another abundant source of oxazoles as part of a structurally functionally diverse class of ribosomally derived peptides, dubbed TOMMs, that are widely disseminated across the phylogenetic spectra of bacterial secretion systems, including potential pathobionts associated with IBD pathogenesis or skin inflammation (Mazmanian et al, 2008; Melby et al, 2011).…”

A Microcapillary Flow Disc Reactor for Organic Synthesis

“…In the first of these reactions, the formation of 4,5-disubstituted oxazoles was investigated since these heterocyclic rings are prevalent in many drug substances and agrochemicals . This system was also selected as its feasibility had already been shown in the preparation of a small collection of oxazoles using a modular flow reactor 15 whereby acid chlorides were reacted with enolisable methylene isocyanides .…”

“…In the first of these reactions, the formation of 4,5-disubstituted oxazoles was investigated since these heterocyclic rings are prevalent in many drug substances and agrochemicals . This system was also selected as its feasibility had already been shown in the preparation of a small collection of oxazoles using a modular flow reactor 15 whereby acid chlorides were reacted with enolisable methylene isocyanides . In these experiments reagents were mixed on a microfluidic 1-mL glass chip with a serpentine microchannel at 60−100 °C followed by base-catalysed cyclisation and scavenging of excess starting material with immobilised reagents placed in prepacked glass tube reactor cartridges (packed bed columns).…”

Crystal structure of diethyl {2,2,2-trichloro-1-[2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-4-methylpentanamido]ethyl}phosphonate

“…Various bacteria and marine organisms produce numerous antibiotics belonging to the oxazole series (Chamberlin et al, 1977;Bertram et al, 2001;Jansen et al,1992;Moody & Bagley, 1998). Today, numerous oxazole-based synthetic bioregulators with strong antimicrobial, cytostatic, immune stimulating, neuroleptic, analgesic, and other kinds of biological activity are known (Turchi et al, 1986;Palmer et al, 2003). In particular, 5-amino-1,3-oxazole and its derivatives are well recognized for their potent and diverse bioregulation activity.…”