Thioamides: synthesis, stability, and immunological activities of thioanalogues of imreg. preparation of new thioacylating agents using fluorobenzimidazolone …

B Zacharie, M Lagraoui, M Dimarco…

Index: Zacharie, Boulos; Lagraoui, Mouna; Dimarco, Marika; Penney, Christopher L.; Gagnon, Lyne Journal of Medicinal Chemistry, 1999 , vol. 42, # 11 p. 2046 - 2052

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Citation Number: 41

Abstract

Imreg (Tyr 1-Gly 2-Gly 3) is a well-known immunostimulant. However, it possesses a short half-life. Stabilized analogues of Imreg were prepared by a regioselective insertion in which peptide bonds at position 1, 2 or 2, 3 were replaced by thioamide linkages. This was achieved by using new thioacylating agents based on thioacyl-fluoro-N-benzimidazolone. The synthesis and properties of these reagents are described herein. This peptide ...