A facile synthesis of N-Z/Boc-protected 1,3,4-oxadiazole-based peptidomimetics employing peptidyl thiosemicarbazides

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• 作者：Ravi S. Lamani ; G. Nagendra ; Vommina V. Sureshbabu
• 关键词：Peptidomimetics ; Amino acid hydrazides ; Peptidyl thiosemicarbazides ; Cyclization ; 1 ; 3 ; 4-Oxadiazoles
• 刊名：Tetrahedron Letters
• 出版年：2010
• 出版时间：8 September 2010
• 年：2010
• 卷：51
• 期：36
• 页码：4705-4709
• 全文大小：713 K

文摘

Synthesis of 1,3,4-oxadiazole containing peptidomimetics is described by a p-TsCl/pyridine-mediated cyclization of the corresponding dipeptidyl thiosemicarbazides, which are readily prepared by coupling N-protected amino acid hydrazides with amino acid-derived isothiocyanato esters. Further, the protocol has also been extended for the synthesis of orthogonally protected 1,3,4-oxadiazole tethered mimetics as well. The synthetic route is simple and mild conditions are used so that the chirality of the starting amino acids is retained.