Abstract
•Carboximidamides 4-10 and 4,5-dihydro-1H-imidazol-2-amines 11, 12 were synthesized.•Carboximidamide 4 reacted with different acid-chlorides.•X-ray crystallography of 15 has been determined.•The new two compounds 6 and 8 were evaluated for their in vivo antihyperglycemic.•ALT, AST, urea, creatinine, triglyceride and cholesterol in serum were determined.
Carboximidamides 4-10 and 4,5-dihydro-1H-imidazol-2-amines 11, 12 linked with pyrimidine moiety were obtained via reaction of N-(pyrimidin-2-yl)cyanamides 1-3 with amines such as; morpholine, piperidine, piperazines and/or ethylenediamine, respectively. N-(4,6-Dimethylpyrimidin-2-yl)morpholine-4-carboximidamide 4 is subjected to react with 4-methylbenzenesulphonyl-, benzoyl-, and/or terephthaloyl chloride to give the corresponding N-substituted carboximidamides 13-16. The structure of new compounds was confirmed by using FT-IR and NMR spectral data. X-ray single crystal diffraction analysis of 15 revealed that the structure belongs to the monoclinic system and has a chair conformation in a morpholine ring. DMSO and carboximidamides 6, 8 caused a significant decrease in the serum level of glucose, comparing with the diabetic-treated group (streptozotocin-treated group). Furthermore they restored the serum levels of ALT, AST, triglyceride and cholesterol (Biomarker of liver function) to the levels similar or slightly higher than of the negative control group. Also, the biomarkers of kidney function (serum urea and creatinine) were restored to the level urea or slightly higher than their negative control on the administration of DMSO and carboximidamides 6, 8. So it can be concluded that, DMSO and carboximidamides 6, 8 may be used as ameliorative agents against streptozotocin-induced a pathological effects on blood glucose, liver function and kidney function. Morever, it can be stated that these compounds may be more effective in reducing the pathological effects of streptozotocin-induced diabetes than that of metformin.
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