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  • Title: Antimitotic and vascular disrupting agents: 2-hydroxy-3,4,5-trimethoxybenzophenones.
    Author: Chang CY, Chuang HY, Lee HY, Yeh TK, Kuo CC, Chang CY, Chang JY, Liou JP.
    Journal: Eur J Med Chem; 2014 Apr 22; 77():306-14. PubMed ID: 24657567.
    Abstract:
    2-Hydroxy-3,4,5-trimethoxybenzophenones (8-16) manifest pseudo-ring formation involving intramolecular hydrogen bonding of the 2-OH and the carbonyl group. Among the synthetic products described in this report, (3-hydroxy-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxyphenyl)-methanone (14) and (3-amino-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxy-phenyl)methanone (16) exhibit significant antiproliferative activity against KB cells with IC50 values of 11.1 and 11.3 nM, respectively. These two compounds also displayed tubulin affinity comparable to that of combretastatin A-4. In studies with human umbilical vein endothelial cells, compounds 14 and 16 revealed concentration-dependent vascular-disrupting properties. The results support the rationale of the pseudo-ring concept and suggest further investigation of A-ring modification in these benzophenones.
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