Lomevactone
From Wikipedia, the free encyclopedia
- None
- 81478-25-3
(3R,4R,6R): 82510-81-4
rel-(3R,4R,6R): 75115-73-0
 | |
| Clinical data | |
|---|---|
| ATC code |
|
| Identifiers | |
| |
| CAS Number |
|
| PubChem CID | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C18H17ClO2 |
| Molar mass | 300.78 g·mol−1 |
| 3D model (JSmol) | |
| |
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.[1][2]
There are eight possible stereoisomers of lomevactone. It is the (3R,4R,6R)-form that has the psychotherapeutic properties.[3][4]
(3R,4R,6R)-Lomevactone
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
- ↑ David J. Triggle (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ Axiotis, S. et al, Eur. J. Med. Chem.-Chim. Ther., 1981, 16, 431, 439.
- ↑ Pierre Simon & Jacques Dreux, U.S. patent 4,287,206 (1981 to Sanofi Aventis France).
- ↑ 시몽 삐에르 & 드로 짝끄, KR830002288 (1983).
| |||||||||||||||||||||
| |||||||||||||||||||||
| |||||||||||||||||||||
| |||||||||||||||||||||
| |||||||||||||||||||||
 | This drug article relating to the nervous system is a stub. You can help Wikipedia by adding missing information. |