A convenient synthesis of 1,3,4-thiadiazole and 1,3,4-oxadiazole based peptidomimetics employing diacylhydrazines derived from amino acids

Abstract

a b s t r a c tSynthesis of novel orthogonally protected 1,3,4-thiadiazole and 1,3,4-oxadiazole tethered dipeptide mimetics is described. Both the heterocycles are prepared via a set of diacylhydrazines derived from amino acids. 1,3,4-Thiadiazoles are synthesized by dehydrosulfurization using Lawesson's reagent while 1,3,4-oxadiazoles are obtained by EDC mediated cyclodehydration.

Synthetic Approaches and Pharmacological Activity of 1,3,4-Oxadiazoles: A Review of the Literature from 2000–2012

“…Nagendra and co-workers [ 31 ] reported the synthesis of novel orthogonally protected 1,3,4-oxadiazole 56 , tethered dipeptide mimetics, by cyclodehydration of diacylhydrazine 55 using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) as a dehydration agent, obtaining a 70%–92% yields ( Scheme 14 ).…”

A facile route for the synthesis of novel S-linked 1,3,5-triazine tethered peptidomimetics

“…Zhao et al 14 reported the synthesis of N a -Cbz-amino acyl derived 3,5,6-trisubstituted 1,2,4-triazines using Cbz-protected amino acyl hydrazides and 1,2-diones in the presence of excess NH 4 OAc at 180°C. Our group reported several new classes of peptidomimetics possessing heterocycles such as 1,3,4,-oxadiazole, 15 1,2,4,-oxadiazole, 16 1,3,4,-thiadiazole, 17 triazoles 18 and tetrazoles. 19 This list also includes Fmoc-protected amino alkyl S/Se-linked tetrazoles 20 and Z/Boc-protected S-linked oxadiazole tethered peptidomimetics.…”

Synthesis of 1,3,4-oxadiazole derivatives from α-amino acid and acyl hydrazides under thermal heating or microwave irradiation conditions

“…In this context Sureshbabu described the synthesis of 1,3,4-oxadiazole peptidomimetics starting from diacylhydrazines derived from amino acids. 27,28 On the other hand, amino acids have emerged as important building blocks for the synthesis of a range of different compounds. [29][30][31] Moreover, the interest on the biological and medicinal properties of chalcogen amino acids has also been increasingly appreciated, mainly due to their antioxidant, 32 antitumor, 33 antimicrobial, 34 and antiviral 35 properties.…”