Conveniently accessible 4‐[(2‐(3,4‐dimethoxyphenyl)ethyl]‐3‐thiosemicarbazide (2) was converted to new 1‐substituted benzylidene/furfurylidene‐4‐[2‐(3,4‐dimethoxyphenyl)ethyl]‐3‐thiosemicarbazides (3) which furnished 2‐(substituted benzylidene/furfurylidene)hydrazono‐3‐[2‐(3,4‐dimethoxyphenyl)ethyl]thiaz‐olidin‐4‐ones (4) and 1‐(substituted benzylidene/furfurylidene)‐amino‐3‐[2‐(3,4‐dimethoxyphenyl)ethyl]‐2‐thioxo‐4,5‐imidazol‐idinediones (5) on reaction with chloroacetic acid and oxalyl chloride, respectively. The structure of 5 was confirmed by X‐ray diffraction studies performed on 5a. 4 and 5 were evaluated for their potentiating effects on pentobarbital induced hypnosis. Most of the compounds caused remarkable increases in pentobarbital sleeping time.
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A novel series of indolylthiosemicarbazides (6a-6g) and their cyclization products, 4-thiazolidinones (7a-7g), have been designed, synthesized and evaluated, in vitro, for their antiviral activity against a wide range of DNA and RNA viruses. Compounds 6a, 6b, 6c and 6d exhibited notable antiviral activity against Coxsackie B4 virus, at EC50 values ranging from 0.4 to 2.1 μg/mL. The selectivity index (ratio of cytotoxic to antivirally effective concentration) values of these compounds were between 9 and 56. Besides, 6b, 6c and 6d also inhibited the replication of two other RNA viruses, Sindbis virus and respiratory syncytial virus, although these EC50 values were higher compared to those noted for Coxsackie B4 virus. The SAR analysis indicated that keeping the free thiosemicarbazide moiety is crucial to obtain this antiviral activity, since the cyclization products (7a-7g) did not produce any antiviral effect.
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