Pentomone

Pentomone
Clinical data
Other names	Lilly 113935; LY-113935
Drug class	Nonsteroidal antiandrogen
ATC code	None;
Identifiers
	IUPAC name (5aS,6aR,12aS,13aR)-4,8-dimethoxy-6,6-dimethyl-5a,6a,12,12a,13a,14-hexahydrochromeno[3,2-b]xanthen-13-one;
CAS Number	67102-87-8;
PubChem CID	49354;
ChemSpider	44862;
UNII	OPS67T329P;
ChEMBL	ChEMBL2107005;
Chemical and physical data
Formula	C24H26O5
Molar mass	394.467 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1(C2C(CC3=C(O2)C(=CC=C3)OC)C(=O)C4C1OC5=C(C4)C=CC=C5OC)C;
	InChI InChI=InChI=1S/C24H26O5/c1-24(2)22-15(11-13-7-5-9-17(26-3)20(13)28-22)19(25)16-12-14-8-6-10-18(27-4)21(14)29-23(16)24/h5-10,15-16,22-23H,11-12H2,1-4H3/t15-,16+,22-,23+; Key:MTJTVTZUEKVNTG-YJEDKTMASA-N;

Pentomone (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name) (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]

Synthesis

Condensation of two equivalents of o-vanillin with 4,4-dimethylcyclohexadienone (2) gives the five-ring ketone derivative (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 then reduces both olefin pi-bonds as well as the ketone, to give (4). Re-oxidation of the alcohol thus formed with pyridinium chlorochromate affords pentomone.^[2]^[3]

References

^ ^a ^b 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).

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[Elks2014-1] 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.

[2] Michael E. Flaugh, U.S. patent 4,081,458 (1978 to Eli Lilly And Company).

[3] David A Hall, Richard E Heiney, & Michael E Flaugh, GB1593643 (1981 to Eli Lilly and Co).

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