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Lomevactone

Clinical data
ATC code	None
Identifiers
IUPAC name 4-(4-Chlorophenyl)-6-methyl-3-phenyltetrahydro-2H-pyran-2-one
CAS Number	81478-25-3 (3R,4R,6R): 82510-81-4 rel-(3R,4R,6R): 75115-73-0
PubChem CID	100079
ChemSpider	90435
UNII	TP71SPS85C
CompTox Dashboard (EPA)	DTXSID601024659
Chemical and physical data
Formula	C18H17ClO2
Molar mass	300.78 g·mol
3D model (JSmol)	Interactive image
SMILES Clc1ccc(cc1)C2C(C(=O)OC(C)C2)c3ccccc3

Lomevactone (INN; developmental code name DR-250) is a drug described as a psychostimulant and antidepressant which was synthesized and assayed in the 1980s, but was never marketed.

Stereoisomers

There are eight possible stereoisomers of lomevactone. It is the (3R,4R,6R)-form that has the psychotherapeutic properties.

Synthesis

The conjugate 1,4-alkylation reaction between 4-chlorobenzylideneacetone (1) and phenylacetonitrile (2) gives 3-(4-chlorophenyl)-5-oxo-2-phenylhexanenitrile (3). The selective reduction of the keto group to the alcohol with sodium borohydride gives 3-(4-chlorophenyl)-5-hydroxy-2-phenylhexanenitrile (4). Hydrolysis of the nitrile to an acid gives 3-(4-chlorophenyl)-5-hydroxy-2-phenylhexanoic acid. This is followed by lactone formation completing the synthesis of lomevactone (5).

References

1. David J. Triggle (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9.
2. Poncelet M, Chermat R, Soubrie P, Simon P (1983). "The progressive ratio schedule as a model for studying the psychomotor stimulant activity of drugs in the rat". Psychopharmacology. 80 (2): 184–9. doi:10.1007/BF00427967. PMID 6136063. S2CID 2372145.
3. Axiotis, S.; Druex, J.; Perrin, M.; Royer, J. (1982). "Conformations in the tetrahydropyran-2-one ring". Tetrahedron. 38 (4): 499–504. doi:10.1016/0040-4020(82)80093-8.
4. Axiotis, S., Sollier, J.-C., Dreux, J., Chermat, R., Poncelet, M., Simon, P. (July 1987). "Tétrahydropyrones-2 III. Recherche d'une activité psychostimulante spécifique". European Journal of Medicinal Chemistry. 22 (4): 293–303. doi:10.1016/0223-5234(87)90266-2.
5. Axiotis, S. et al, Eur. J. Med. Chem.-Chim. Ther., 1981, 16, 431, 439.
6. Pierre Simon & Jacques Dreux, U.S. patent 4,287,206 (1981 to Sanofi Aventis France).
7. 시몽 삐에르 & 드로 짝끄, KR830002288 (1983).

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