Document Type : Original Article
Authors
1
Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy , Assiut University, Assiut-71526, Egypt
2
Department of Parasitology, Faculty of Medicine, Assiut University, Assiut-71526, Egypt
Abstract
The purpose of this study based upon design and synthesis of a new series of 1,4-
disubstituted piperazine-2,3-dione derivatives through two steps reaction. This protocol
involves the formation of N,N\-Bis-(4-substituted benzyl)-ethane-1,2-diamine and N,N\-Bis-[1-
(4-substituted phenyl)-ethyl]-ethane-1,2-diamine derivatives (1a-i) through reductive alkylation
reaction from ethylenediamine and different carbonyl compounds in the presence of sodium
cyanoborohydride. The second step involves reaction of compounds (1a-i) with diethyl oxalate
affording the target compounds. Consequently, nine new 1,4-disubstituted piperazine-2,3-dione
derivatives were synthesized as the target compounds, 1,4-Bis-(4-substituted benzyl)-
piperazine-2,3-dione and 1,4-Bis-[1-(4-substituted phenyl)-ethyl]-piperazine-2,3-dione
derivatives (2a-i). The structures of the target compounds were elucidated depending upon the
data of the different spectral as well as the elemental methods of analyses. In addition, a mass
spectrum, for a representative example, was carried out where the expected fragmentation
pattern is in accordance with the structure of the considered compound. The lipophilicity of the
target compounds as expressed from the ClogP and the measured R f remarkably supercede that
of piperazine. The preliminary anthelmintic activity of the newly synthesized derivatives (2a-i)
was investigated in vitro against Enterobiuos vermicularis and Fasciola hepatica. The tested
compounds exhibited, in all cases, considerable inhibitory effects on the growth of the tested
parasites in comparison with piperazine hydrate as a reference drug.
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