Abstract
Condensation of benzil (1) with urea, monophenyl urea and diphenyl urea in the presence of absolute ethanol using 30% aqueous NaOH gave the products 1a, 1b and 1c respectively and also with thiourea, monomethyl thiourea, dimethyl thiourea and diethyl thiourea the products 2a, 2b, 2c and 2d were obtained. Methylation of the product, 2a in the presence of dimethyl formamide (DMF) using K2CO3 formed 2. The compounds 1b, 1c, 2b, 2c and 2 showed highly cytotoxic activity and the compounds 1a, 2a, 2d showed relatively low cytotoxic activity against brine shrimp lethality bioassay.
Highlights
Several types of substituted isatin heterocyclic derivatives were synthesized and found cytotoxic activity of these compounds by screening tests (Islam et al, 2001a; Islam et al, 2001b; Lingcon et al, 2001)
Simple base catalyzed condensation of benzil, 1 with urea, monophenyl urea and diphenyl urea in absolute ethanol furnished 1a, 1b, 1c whereas with thiourea, methyl thiourea, dimethyl thiourea and diethyl thiourea gave 2a, 2b, 2c and 2d. The formation of these products follows the pinacole-pinacolone type (Shukla and Trivedi, 1997) rearrangement that is shown in the Scheme 2
The IR spectrum of the compound, 1a at 3271 cm-1 indicates the presence of NH group of amide moiety
Summary
Several types of substituted isatin heterocyclic derivatives were synthesized and found cytotoxic activity of these compounds by screening tests (Islam et al, 2001a; Islam et al, 2001b; Lingcon et al, 2001). The product, 1a was recrystallized by ethanol, dried, the m.p. 294-295oC and yields 0.750 g (80%). 1; (0.148 g, 0.70 mmol/L) and the monophenylurea; (0.298 g, 1.40 mmol/L) in the molar ratio of ca 1:2 were refluxed in the absolute ethanol and the procedure for 1b was similar to that of the compound, 1a.
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