New routes to 2, 4, 5-trisubstituted oxazoles were established whereby the substitution pattern was established by the structure of the starting nonsymmetrical acyloins. 2-Chloromethyl-4, 5-disubstituted oxazoles were prepared by refinements of an earlier described process whereby chloroacetyl esters of symmetrical and non-symmetrical acyloins were cyclized using an ammonium acetate/acetic acid protocol. After substitution is effected, the azide moiety is then installed by substitution under mild conditions. While dibrominated and iodinated phenyloxazoles are required for further synthetic elaboration, the cyclization reaction was found to be very sensitive to the relative positions of the halogens in the starting materials.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4480780 | PMC |
| http://dx.doi.org/10.1016/j.tetlet.2014.11.014 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A multi-valent polymyxin-based fluorescent probe for the detection of Gram-negative infections.
J Mater Chem B
January 2025
Precision Healthcare University Research Institute, Queen Mary University of London, Empire House, London, E1 1HH, UK.
A multi-branched fluorogenic probe for the rapid and specific detection of Gram-negative bacteria is reported. Three Gram-negative-targeting azido-modified polymyxins were clicked onto a trivalent scaffold functionalised with the environmental green-emitting fluorophore 7-nitrobenz-2-oxa-1,3-diazole. The probe allowed wash-free detection of target bacteria with increased sensitivity and lower limits of detection compared to monovalent probes.
View Article and Find Full Text PDFWe present a transition metal-free approach to 2--substituted indenones, cyclopentenones, and 4-carbonyl oxazoles, based on the reaction of 5-acylated -fluoroalkyl substituted 1,2,3-triazoles (prepared by a three-component click reaction of copper acetylides, fluoroalkyl azides, and acyl chlorides) with Lewis acids aluminium trichloride or boron trifluoride etherate, proceeding the generation and cyclization of vinyl cations.
View Article and Find Full Text PDFSynthesis of sydnonimines from sydnones and their use for bioorthogonal release of isocyanates in cells.
Chem Commun (Camb)
March 2024
Département Médicaments et Technologies pour la Santé (DMTS), CEA, INRAE, SCBM, Université Paris Saclay, Gif-sur-Yvette 91191, France.
In this article, we report the synthesis of sydnonimines from sydnones and their use as dipoles for fast click-and-release reactions. The process relies on nucleophilic aromatic substitution of aliphatic and aromatic amines with triflated sydnones. This new methodology allowed the preparation of functionalised sydnonimine probes that are otherwise difficult to prepare.
View Article and Find Full Text PDFInvestigation of mitochondrial targeting ability of sydnones and sydnonimines and mitochondria-targeted delivery of celecoxib.
Bioorg Med Chem Lett
February 2023
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China. Electronic address:
Mitochondria are considered to be a promising target in cancer diagnosis and therapeutics. Recently, sydnone and sydnonimine, as mesoionic bioorthogonal reagents, have been used in cell labeling and drug delivery. Here we investigated the mitochondrial targeting ability of sydnones and sydnonimines for the first time.
View Article and Find Full Text PDFThe present study aimed to investigate the enzymetic, non-enzymetic toxicity and antioxidant potential of a drug candidate 5-Benzyl-1,3,4-Oxadiazole-2-Thiol(OXPA) using computational tools and in vivo models. The binding pattern of it, with different toxicity/oxidative enzymes was predicted using software pkCSM, Protox- II, LAZAR, Mcule 1-Click Docking 3D-Ligand binding Site and best score obtained used as an evaluating criterion. After acute oral toxicity, in vivo.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!