1236188-80-9Relevant articles and documents
Regioselective Epoxide Ring Opening for the Stereospecific Scale-Up Synthesis of BMS-960, A Potent and Selective Isoxazole-Containing S1P1 Receptor Agonist
Hou, Xiaoping,Zhang, Huiping,Chen, Bang-Chi,Guo, Zhiwei,Singh, Amarjit,Goswami, Animesh,Gilmore, John L.,Sheppeck, James E.,Dyckman, Alaric J.,Carter, Percy H.,Mathur, Arvind
, p. 200 - 207 (2017/02/26)
This article presents a stereospecific scale-up synthesis of (S)-1-((S)-2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidine-3-carboxylic acid (BMS-960), a potent and selective isoxazole-containing S1P
Potent and Selective Agonists of Sphingosine 1-Phosphate 1 (S1P1): Discovery and SAR of a Novel Isoxazole Based Series
Watterson, Scott H.,Guo, Junqing,Spergel, Steve H.,Langevine, Charles M.,Moquin, Robert V.,Shen, Ding Ren,Yarde, Melissa,Cvijic, Mary Ellen,Banas, Dana,Liu, Richard,Suchard, Suzanne J.,Gillooly, Kathleen,Taylor, Tracy,Rex-Rabe, Sandra,Shuster, David J.,McIntyre, Kim W.,Cornelius, Georgia,D'Arienzo, Celia,Marino, Anthony,Balimane, Praveen,Warrack, Bethanne,Salter-Cid, Luisa,McKinnon, Murray,Barrish, Joel C.,Carter, Percy H.,Pitts, William J.,Xie, Jenny,Dyckman, Alaric J.
, p. 2820 - 2840 (2016/04/10)
Sphingosine 1-phosphate (S1P) is the endogenous ligand for the sphingosine 1-phosphate receptors (S1P1-5) and evokes a variety of cellular responses through their stimulation. The interaction of S1P with the S1P receptors plays a fundamental physiological role in a number of processes including vascular development and stabilization, lymphocyte migration, and proliferation. Agonism of S1P1, in particular, has been shown to play a significant role in lymphocyte trafficking from the thymus and secondary lymphoid organs, resulting in immunosuppression. This article will detail the discovery and SAR of a potent and selective series of isoxazole based full agonists of S1P1. Isoxazole 6d demonstrated impressive efficacy when administered orally in a rat model of arthritis and in a mouse experimental autoimmune encephalomyelitis (EAE) model of multiple sclerosis.
Synthesis of ethyl 3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxylate via regioselective dipolar cycloaddition
Schmidt, Michael A.,Katipally, Kishta,Ramirez, Antonio,Soltani, Omid,Hou, Xiaoping,Zhang, Huiping,Chen, Bang-Chi,Qian, Xinhua,Deshpande, Rajendra P.
scheme or table, p. 3994 - 3997 (2012/08/28)
Efforts to prepare ethyl 3-phenyl-4-(trifluoromethyl)isoxazole-5- carboxylate (1) by developing a regioselective 1,3-dipolar cycloaddition between phenyl nitrile oxide and various 4,4,4-trifluoromethyl crotonates are described. The substitution at the C2-position of crotonate dipolarophile 4 significantly influenced the regiochemistry and yield of the cycloaddition. Enol and enol ether-based crotonates underwent regioselective cycloadditions with phenyl nitrile oxide to provide 4-trifluoromethyl isoxazoles in good yields.
