Synthesis and antihepatotoxic activity of some new chalcones containing 1, 4 - dioxane ring system

Silybum marianum is a medicinal plant used widely for treating liver diseases. The silymarin, a mixture of three flavolignan isomers namely silybin (1), silydianin (2), and silychristin (3) is an active constituent of the plant. However, silybin containing 1, 4-dioxane ring is the most potent antihepatotoxic agent. In contrast, other isomers do not possess 1, 4-dioxane ring, and thus do not exhibit a significant activity. We, therefore, thought that 1, 4-dioxane ring plays an important role in displaying antihepatotoxic activity, and have prepared some chalcones containing 1, 4-dioxane ring. The synthesized compounds were evaluated for antihepatotoxic activity against carbon tetrachloride induced hepatotoxicity in albino rats. The degree of protection was measured by using biochemical parameters like serum glutamic oxaloacetic transaminase (SGOT), serum glutamic pyruvate transaminase (SGPT), alkaline phosphatase (ALKP), total protein (TP) and total albumin (TA). The compounds namely 2-hydroxy-4-methoxy-3',4'-(2"- hydroxy methyl-1", 4"- dioxano) chalcone (9b) and 2-hydroxy- 4, 6-dimethoxy-3', 4'-(2"-hydroxy methyl-1", 4"- dioxano) chalcone (9c) exhibited a potent activity in comparison to standard drug silybon-70. The other compounds also showed moderate activity.