Patent Evaluation: Moranoline Derivatives as Antiviral Agents

Summary

Novelty: A novel series of moranoline derivatives are disclosed. These compounds are claimed to have antiviral activity and are potentially useful for the treatment of viral diseases, such as HIV.

Biology: The cell degeneration effect (CPE) observed in cells to which the drug was added was compared to controls (N-n-butylmoranoline and N-ethylmoranoline) and expressed as an MIC (the amount of drug whereby 50% of CPE was produced). Two specific compounds had MICs of 1 μg/ml compared with > 100 for the controls and demonstrated anti-HIV activity with IC₅₀s of 0.1 and 0.3 μg/ml compared with 40.8 μg/ml for moranoline. Both compounds had LD₅₀s (ip) > 300 mg/kg (po) > 5000 mg/kg in mice.

Chemistry: No experimental details are included but 207 compounds are exemplified. The preferred compounds are N-[4-(4-phenoxyphenyl)-3-pentenyl]moranoline (115) and N-[4-(4-chlorophenoxy)butyl]moranoline (141).

Structure: