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Synthesis, characterization, antioxidant, antidiabetic, anticholinergic, and antiepileptic properties of novel N‐substituted tetrahydropyrimidines based on phenylthiourea
Author(s) -
Maharramova Gunel,
Taslimi Parham,
Sujayev Afsun,
Farzaliyev Vagif,
Durmaz Lokman,
Gulçin İlhami
Publication year - 2018
Publication title -
journal of biochemical and molecular toxicology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.526
H-Index - 58
eISSN - 1099-0461
pISSN - 1095-6670
DOI - 10.1002/jbt.22221
Subject(s) - chemistry , dpph , acetylcholinesterase , antioxidant , aché , sulfonamide , salicylaldehyde , trifluoroacetic acid , organic chemistry , enzyme , medicinal chemistry , stereochemistry , schiff base
In the presence of trifluoroacetic acid, on the basis of three‐component condensation of phenylthiourea with its salicylaldehyde and methyl‐3‐oxobutanoate, an efficient method for the synthesis of 1‐(4‐(2‐hydroxyphenyl)‐6‐methyl‐1‐phenyl‐2‐thioxo‐1,2,3,4‐tetrahydropyrimidin‐5‐yl)ethanone (I) has been worked out. These novel N‐substituted tetrahydropyrimidines based on phenylthiourea showed good inhibitory action against acetylcholinesterase (AChE), α‐glycosidase, and human carbonic anhydrase (hCA) isoforms I and II. K i values of AChE enzyme were in the range of 0.48 to 7.46 nM. The hCA I and II were effectively inhibited by the compounds, with K i values in the range of 502.44 to 923.11 nM for hCA I and 400.32 to 801.57 nM for hCA II, respectively. The antioxidant activity of the novel N‐substituted tetrahydropyrimidines based on phenylthiourea was investigated by using different in vitro antioxidant assays; including 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH·) radical scavenging, Cu 2+ and Fe 3+ reducing activities.