Abstract
N-Aryl-C-ethoxycarbonylnitrile imines (3a-g) react with ethyl cyanoacetate 1 in 1,3-dipolar cycloaddition to yield novel pyrazole-3,4-dicarboxylates (4a-g) in moderate yields. The reaction of pyrazole-3,4-dicarboxylates (4a, d) with hydrazine afforded pyrazolo[4,3-d]pyridazine-4,7-diones (5a, d) in good yields. All compounds were fully characterized by spectroscopic methods. Some of the newly synthesized compounds were evaluated for their cytotoxic activity against murine P815 mastocytoma cell line.
Highlights
Pyrazole and its derivatives, occupy an important position in medicinal chemistry with a wide range of bioactivities
Some of the newly synthesized compounds were evaluated for their cytotoxic activity against murine P815 mastocytoma cell line
The ethyl hydrazono-α-bromoglyoxylates (2a-g) (Figure 1) selected to generate the corresponding N-aryl-C-ethoxycarbonylnitrile imines were prepared from the reaction of the adequate diazonium salts with ethyl acetoacetate, followed by bromination of the resulting azoacetoacetic esters [18]
Summary
Occupy an important position in medicinal chemistry with a wide range of bioactivities. They possess anti-obesity [1], receptor antagonists [2], HIV reverse transcriptase inhibitors [3], and anti-hyperglycemic activities [4]. Despite numerous diverse approaches toward syntheses of pyrazoles developed so far, it is still challenging to prepare polysubstituted pyrazoles with various substituents from readily available building blocks. We report a facile approach to provide polysubstituted pyrazoles via 1,3-dipolar cycloaddition of ethyl cyanoacetate with N-Aryl-Cethoxycarbonylnitrile imines. Evaluation of their cytotoxic activity toward cell line P815 is reported
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