25740-75-4Relevant academic research and scientific papers
Development of Potent 3-Br-isoxazoline-Based Antimalarial and Antileishmanial Compounds
Basilico, Nicoletta,Conti, Paola,Coser, Consuelo,Galbiati, Andrea,Parapini, Silvia,Tamborini, Lucia,Taramelli, Donatella,Zana, Aureliano
supporting information, p. 1726 - 1732 (2021/11/01)
Starting from the structure of previously reported 3-Br-isoxazoline-based covalent inhibitors of P. falciparum glyceraldehyde 3-phosphate dehydrogenase, and with the intent to improve their metabolic stability and antimalarial activity, we designed and synthesized a series of simplified analogues that are characterized by the insertion of the oxadiazole ring as a bioisosteric replacement for the metabolically labile ester/amide function. We then further replaced the oxadiazole ring with a series of five-membered heterocycles and finally combined the most promising structural features. All the new derivatives were tested in vitro for antimalarial as well as antileishmanial activity. We identified two very promising new lead compounds, endowed with submicromolar antileishmanial activity and nanomolar antiplasmodial activity, respectively, and a very high selectivity index with respect to mammalian cells.
An efficient synthesis and antimicrobial evaluation of 5-alkenyl- and 5-styryl-1,2,4-oxadiazoles
Tarasenko, Marina,Sidneva, Vera,Belova, Alexandra,Romanycheva, Anna,Sharonova, Tatyana,Baykov, Sergey,Shetnev, Anton,Kofanov, Eugeniy,Kuznetsov, Mikhail A.
, p. 458 - 470 (2019/03/07)
The cyclodehydration of O-acylamidoximes at room temperature in the superbase system KOH/DMSO represents a simple and efficient way to 5-alkenyl- and 5-styryl-1,2,4-oxadiazoles. This method is suitable for the preparation of 5-(4-vinylphenyl)-1,2,4-oxadia
Tuned methods for conjugate addition to a vinyl oxadiazole; Synthesis of pharmaceutically important motifs
Burns, Alan R.,Kerr, Jennifer H.,Kerr, William J.,Passmore, Joanna,Paterson, Laura C.,Watson, Allan J. B.
experimental part, p. 2777 - 2783 (2010/08/20)
The addition of various nucleophiles to a vinyl 1,2,4-oxadiazole is described. Following optimisation, individual protocols tuned for the use of each specific class of reagent have been developed to allow the installation of nitrogen, sulfur, oxygen, and carbon nucleophiles, and leading to the preparation of a series of compounds containing the pharmaceutically important oxadiazole motif.
