Pentomone
Pentomone (INN, USAN) (developmental code name Lilly 113935 or LY-113935) is a nonsteroidal antiandrogen (NSAA) described as a "prostate growth inhibitor" which was never marketed.[1] It was synthesized and assayed in 1978.[1]
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| Other names | Lilly 113935; LY-113935 |
| Drug class | Nonsteroidal antiandrogen |
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| Formula | C24H26O5 |
| Molar mass | 394.467 g·mol−1 |
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Synthesis
Condensation of o-vanillin (2-Hydroxy-m-anisaldehyde) with 4,4-dimethylcyclohexadienone [1073-14-9] (2) proceeds twice to give 4,8-Dimethoxy-6,6-dimethyl-5a,6a-dihydrochromeno[3,2-b]xanthen-13-one, PC20360051 (3). The reaction may be visualized as initial conjugate addition of phenoxide to the enone followed by interception of the resulting anion by the aldehyde carbonyl group. Catalytic hydrogenation of the intermediate reduces both of the olefin pi-bonds as well as the carbonyl group (4). Back oxidation of the alcohol thus formed with pyridinium chlorochromate affords pentomone (5).
References
- Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 949–. ISBN 978-1-4757-2085-3.
- Michael E. Flaugh, U.S. patent 4,081,458 (1978 to Eli Lilly And Company).
- David A Hall, Richard E Heiney, & Michael E Flaugh, GB1593643 (1981 to Eli Lilly and Co).