Various aliphatic and aromatic nitro compounds were selectively and rapidly reduced to their corresponding amino derivatives in very good yield using anhydrous ammonium formate as a catalytic hydrogen transfer agent. Selective and rapid reductLon of nitro compounds is still area of considerable synthetic interestl, particularly when a molecule has several other reducible moieties. Numerous new reagents*-l4 have been developed for reduction of aromatic nitro compounds, however little attention has been paid to the reduction of aliphatic nitro compound&ry,S, which are traditionally reduced by high pressure catalytic hydrogenation 15,16* In the past 30 years catalytic transfer hydrogenation 17-** has demonstrated great potential value in organic and biological chemistry.
A new series of estradiol analogs was synthesized in an attempt to improve on the anticancer activity of 2-methoxyestradiol, a naturally occurring mammalian tubulin polymerization inhibitor. The compounds were evaluated as inhibitors of tubulin polymerization and the binding of [3H]colchicine to tubulin, as well as for in vitro cytotoxicity in human cancer cell cultures. Overall, the most potent of the new compounds were 2-(2',2',2'-trifluoroethoxy)-6-oximinoestradiol, 2-ethoxy-6-oximinoestradiol, and 2-ethoxy-6-methoximinoestradiol. These agents lacked significant affinity for the estrogen receptor. The cytotoxicities of the compounds correlated in general with their abilities to inhibit tubulin polymerization, thus supporting inhibition of tubulin polymerization as the primary mechanism causing inhibition of cell growth.
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