Abstract
In this study, new α-indolylacrylate derivatives were synthesized by the reaction of 2-substituted indoles with various pyruvates using a Brønsted acid ionic liquid catalyst in butyl acetate solvent. This is the first report on the application of pyruvate compounds for the synthesis of indolylacrylates. The acrylate derivatives could be obtained in good to excellent yields. A preliminary biological evaluation revealed their promising anticancer activity (IC50 = 9.73 μM for the compound 4l) and indicated that both the indole core and the acrylate moieties are promising for the development of novel anticancer drugs. The Lipinski's rule and Veber's parameters were assessed for the newly synthesized derivatives.
Highlights
The chemistry of indoles is an extensive research topic in organic synthesis because indole derivatives have unique biological activities.[1]
We investigated the possibility of using reactive carbonyl compounds, i.e. pyruvates, for the synthesis of a-indolylacrylate derivatives under green conditions, and to our delight, highest reactivity of pyruvate with indole was observed in a biphasic system with an ionic liquid as a catalyst and butyl acetate as a solvent
We used our system 1a/butyl acetate[12] in a simple protocol involving the reaction of 2-methyl indole with ethyl pyruvate as a model reaction (Table 1); this is the rst report on the application of pyruvate compounds for the synthesis of a-indolylacrylate derivatives and replacement of dipolar, aprotic, and hazardous solvents by butyl acetate
Summary
The chemistry of indoles is an extensive research topic in organic synthesis because indole derivatives have unique biological activities.[1].
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