A pioneer in designing and synthesizing antimetabolites
Chapter 28, Problem 28.7(choose chapter or problem)
A pioneer in designing and synthesizing antimetabolites that could destroy cancer cells was George Hitchings at the Burroughs Wellcome Company. In 1942, he initiated a program to discover DNA antimetabolites, and in 1948, he and Gertrude Elion synthesized 6-mercaptopurine, a successful drug for treating acute leukemia. Another DNA antimetabolite synthesized by Hutchings and Elion was 6- thioguanine. Hitchings and Elion along with Sir James W. Black won the 1988 Nobel Prize for physiology or medicine for their discoveries of important principles of drug treatment. In each drug, the oxygen at carbon 6 of the parent molecule is replaced by divalent sulfur. Draw structural formulas for the enethiol (the sulfur equivalent of an enol) forms of 6-mercaptopurine and 6-thioguanine. HN S N N 6 N H 6-Mercaptopurine 6-Thioguanine HN S N N 6 N H2N H
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