Isoxazolylthioamides as potential immunosuppressants a combinatorial chemistry approach.

Basic Information

ID: ALA1131369

Journal: Bioorg Med Chem Lett

Title: Isoxazolylthioamides as potential immunosuppressants a combinatorial chemistry approach.

Authors: Albert R, Knecht H, Andersen E, Hungerford V, Schreier MH, Papageorgiou C.

Abstract: A library of thioamide derivatives of leflunomide 1a and of its bioactive metabolite 1b has been synthesised on solid phase. Thus, para-substituted phenylacetic acids were coupled to TentaGel and were subsequently reacted with aromatic isothiocyanates. Treatment of the resulting enaminothioamides with hydroxylamine led to their simultaneous cyclisation and cleavage from the resin affording 2-25. Their in vitro profiling demonstrated that the amide-thioamide isologous substitution was detrimental of the biological activity.

CiteXplore: 9873513

DOI: 10.1016/s0960-894x(98)00365-5

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