STRUCTURAL MODIFICATION AND CYTOTOXIC ACTIVITY OF ADENOSINE

AIM: In order to find new type of antitumor compounds and study the contribution of hydroxyl groups on the sugar part to the antitumor activity of 8-Cl-adenosine, the retinoid analogs of adenosine and the derivatives of 8-Cl-adenosine were synthesized. METHODS: Based on the antitumor activity and structural feature of 8-chloroadenosine and retinoic acid, modifications were made at positions 5′ and 8, (un)substituted cinnamoyl and benzoyl groups were bound at 8 position through amido and ester bonds, sulfonation and nitrosation at 5′-OH and its direct chlorination were conducted. RESULTS: Eleven new compounds were synthesized, they were (6～12), (16), (18～20). CONCLUSION: The cytotoxic activity to HL-60, BIU, and KB of the new compounds were not great. Modifications on the 5′-OH and other hydroxyl groups influenced the cytotoxic activities of 8-Cl-adenosine significantly. It is sugested that the substitutions at position 8 and the hydroxyl groups on the sugar ring play an important role for the antitumor activity of adenosine analogs.