Croatica Chemica Acta, Vol. 90 No. 3, 2017.
Original scientific paper
https://doi.org/10.5562/cca3122
Michael Cyclization of Polarized Systems: Synthesis and in vitro Anti-Diabetic Evaluation of Some Novel Pyrimidine, Pyridine, Pyrazole and Pyrazolo[3,4-b ]pyridine Derivatives
Essam A. Soylem
; Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt
Mohammed G. Assy
; Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt
Ghania M. Morsi
; Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt
Abstract
Various interesting heterocycle skeletons were synthesized via Michael type addition reaction with 1,2; 1,3-bidentate nitrogen
and carbon nucleophiles. Cycloaddition of different α,β–unsaturated systems afforded bromopyrimidinone 3/5, bromothiazine 4 and
bromopyrazole 6a/6b pyrazole-1-carboxylate 8, pyridinylmethanone 9, nicotinonitrile 10, pyrazolopyridine 11a/11b, pyran-3-carbonitrile
12/13, chromenopyridine 14 and N-butyrylpyrazolyl-1-butanone 15 derivatives. The structures of the synthesized compounds were
elucidated based on IR, NMR and mass spectral analyses. Group of the newly synthesized compounds were screened for their anti-diabetic
activities, whereas compounds 8 and 11b exhibited promising anti-diabetic activities at micro molar concentration against α-glucosidase
inhibitor with IC50 values ranging between 13.80-500 μM. On the other hand compound 10 showed a week effect as compared to the
standard anti-diabetic agent.
This work is licensed under a Creative Commons Attribution 4.0 International License.
Keywords
pyrimidine; nicotinonitrile; pyrazolopyridine; chromenopyridine; anti-diabetic
Hrčak ID:
189716
URI
Publication date:
18.12.2017.
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