Abstract
Twelve new bis-Schiff bases of isatin, benzylisatin and 5-fluoroisatin 3a-3l were prepared by condensation of isatin, benzylisatin and 5-fluoroisatin with primary aromatic amines. The chemical structures of the products were confirmed by 1H- and 13CNMR, IR and mass spectral data. The compounds were screened for antiviral activity against a panel of DNA and RNA viruses. Minimum cytotoxic and minimum virus-inhibitory concentrations of these compounds were determined. Compounds 3c and 3i were the most cytotoxic in HEL cells. These newly synthesized bis-Schiff bases were also tested for their antibacterial and antifungal activities. They did not display activity against S. cerevisiae (ATCC 28383) or C. albicans (CIP 1180-79).
Highlights
Isatin has been known for about 150 years and has been recently found, like oxindole and endogenous polyfunctional heterocyclic compounds, to exhibit biological activity in mammals [1]
Isatin is a synthetically versatile substrate that can be used to prepare a large variety of heterocyclic compounds, such as indoles and quinolines, and as a raw material for drug synthesis [2]
Schiff bases and Mannich bases of isatin are known to possess a wide range of pharmacological properties including antibacterial, [8,9,10] anticonvulsant, [11,12] anti-HIV, [13,14,15,16] antifungal [17,18,19,20] and antiviral activity [21]
Summary
Isatin has been known for about 150 years and has been recently found, like oxindole and endogenous polyfunctional heterocyclic compounds, to exhibit biological activity in mammals [1].
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