Isoxazolylthioamides as potential immunosuppressants a combinatorial chemistry approach.

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

Isoxazolylthioamides as potential immunosuppressants a combinatorial chemistry approach.

Bioorg Med Chem Lett. 1998 Aug 18;8(16):2203-8.

PubMed ID

9873513 [ View in PubMed

]

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.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Leflunomide	Dihydroorotate dehydrogenase (quinone), mitochondrial	IC 50 (nM)	10000	N/A	N/A	Details