Synthesis and Crystal Structure of Benzyl [(1S)-1-(5-amino-1,3,4-oxadiazol-2-yl)-2-phenylethyl]carbamate

Abstract

Abstract:The conversion of Z-phenylalanine hydrazide with cyanogen bromide resulted in the formation of the corresponding 2-amino-1,3,4-oxadiazole by spontaneous cyclization of the intermediary cyanohydrazide. The molecular structure of the product was confirmed by single crystal X-ray diffraction. Crystals of the title compound where obtained from a saturated solution in a mixture of petroleum ether and ethyl acetate and belong to the monoclinic space group P2 1 with unit cell parameters a = 9.8152(2) Å, b = 9.6305(2) Å, c = 9.8465(2) Å, β = 116.785(1)°. The asymmetric unit contains one molecule.

Synthesis and X-ray Crystal Structure of N’-Cyano-N,N’-dimethyl-4-nitrobenzohydrazide

“…N'-Cyanohydrazides are only existent if both nitrogen atoms are at least methylated because unsubstituted or monoalkylated derivatives tend to cyclize [1,2]. Those analogues, which bear an amino acid-derived acyl moiety, so-called azapeptide nitriles, have been shown to be highly potent inhibitors of cysteine proteases [1,[3][4][5].…”

A Review on Azapeptides: The Promising Peptidomimetics

“…The front runner cathepsin K inhibitors odanacatib is a non basic and non-lysosomotropic peptidomimetic nitrile and is widely used once weekly treatment for osteoporosis [61,62]. Based on the significance of nitrile type inhibitors aza dipeptide nitriles have been introduced as a new class of inhibitors [63]. Further, the chemo type of 3-cyano-3-aza-β-amino acid derivatives was designed in which the N-cyano group is centrally arranged to allow for interaction with the unprimed and primed binding regions of cathepsin K [64].…”