Abstract
Synthetic and natural spiroxindoles are important anti-inflammatory, antibacterial, antileishmanial, and anticancer agents. In this study, we prepared a spiroxindole derivative and evaluated the preliminary results of its biological activity including anti-inflammatory, antileishmanial, and cytotoxic activity against 3T3 and Hela cell lines. By adopting the 1,3-dipolar cycloaddition reaction, we were able to successfully combine olefin, isatin, and an amino acid to form the desired spiroxindole analog 4 (yield, up to 94%). To elucidate the chemical structure of 4, the X-ray single crystal diffraction technique was employed, and the electronic and NMR spectra of 4 were calculated using the B3LYP/6-311G(d,p) method. The calculated 1H and 13C NMR chemical shifts aligned well with the experimental data. Compound 4 was then evaluated for its anti-inflammatory, antileishmanial, and cytotoxic activity against 3T3 and Hela cell lines. This spiroxindole pyrothiazole (IC50 = 65.9 ± 6.6 μM) showed weak anti-inflammatory activity compared to the test standard, ibuprofen (IC50 = 11.2 ± 1.9 μM), and moderate anticancer activity against Hela cell lines compared to doxorubicin (IC50 = 1.2 ± 0.4 μM vs IC50 = 11.2 ± 0.3 μM for 4). Compound 4 also appeared as an effective antileishmanial agent (IC50 = 39.8 ± 0.43 μM) when tested in vitro.
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•The manuscript involved to design a new spiroindolone pyrothiazole analog.•The designed compound was assigned by X-ray single crystal.•In vitro screening of the designed compound were carried out.•Computational studies of the designed compound were investigated.