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Synthesis and Biological Evaluation of Novel R1, R2 Substituted 2-(4-((2-(4-alkoxyphenyl)-5-methyloxazol-4-yl)Methyl)-1-alkyl-5-methyl-1h-pyrazol-3-yloxy)-6-(Hydroxymethyl)Tetrahydro-2h-pyran-3,4,5-triol Having Anti Diabetic Activity
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The synthesis and biological evaluation of novel pyrazole based heterocycles attached to sugar moiety lead to creating a new molecular frame work. Nine new compounds were synthesized by reacting ethyl 2-((2-(4-methoxyphenyl)-5-methyloxazol-4-yl) methyl)-3-oxobutanoate derivatives (9a-9c) with different alkyl hydrazines to give various substituted 4-((2-(4-methoxyphenyl)-5-methyloxazol-4-yl) methyl)-5-methyl-1H-pyrazol-3-ol derivatives (10 a-10i) which in turn were reacted with bromoglucose (3)to yield R1, R2 substituted 2-(4-((2-(4-alkoxyphenyl)-5-methyloxazol-4-yl)methyl)-1-alkyl-5-methyl-1H-pyrazol-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (12a-12i). The chemical structures of the synthesized compounds were characterized by means of IR, Mass and NMR spectroscopy. The compounds were screened for anti-diabetic activity by urinary glucose excretion method (UGE). Among the compounds tested, 12f, 12h and12i have exhibited moderate anti-diabetic activity as that of standard drug, remogliflozin. These compounds can be further exploited to get the potent lead compound.
Keywords
Pyrazoles, glucoacetate, Alkylhydrazines, Oxazoles, Mass and NMR spectra, Anti diabetic activity.
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