U-41792

Last updated

U-41792
U-41792.svg
Identifiers
  • 1-[4-(1-adamantyloxy)phenyl]piperidine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C21H29NO
Molar mass 311.469 g·mol−1
3D model (JSmol)
  • C1CCN(CC1)C2=CC=C(C=C2)OC34CC5CC(C3)CC(C5)C4
  • InChI=1S/C21H29NO/c1-2-8-22(9-3-1)19-4-6-20(7-5-19)23-21-13-16-10-17(14-21)12-18(11-16)15-21/h4-7,16-18H,1-3,8-15H2
  • Key:NMFLMLJPBJHWSE-UHFFFAOYSA-N

U-41792 is a small molecule developed by the Upjohn Company as a hypobetalipoproteinemic agent, meaning it lowers levels of beta-lipoproteins, including low-density lipoprotein (LDL) such as apolipoprotein B, in the blood. [1] Elevated LDL levels can lead to early-onset atherosclerosis and increase the risk of heart problems. [2]

U-41792 demonstrated its ability to reduce lipid levels in hyperlipemic rats. [3] [4] [5]

Synthesis

In order to synthesize U-41792, the alcohol of adamantane called 1-adamantanol is reacted with sodium to generate its corresponding alkoxide. This alkoxide then undergoes a nucleophilic aromatic substitution on p-fluoronitrobenzene to form the corresponding ether. This ether is then reduced and alkylated to give U-41792. [1]

N.B. 4-Fluoronitrobenzene has dual use in the synthesis of B777-81 & WAY-213,613 also.

References

  1. 1 2 Lednicer D, Heyd WE, Emmert DE, TenBrink RE, Schurr PE, Day CE (January 1979). "Hypobetalipoproteinemic agents. 2. Compounds related to 4-(1-adamantyloxy)aniline". Journal of Medicinal Chemistry. 22 (1): 69–77. doi:10.1021/jm00187a016. PMID   218007.
  2. ↑ Castañer J, Thorpe P (1979). "U-41792". Drugs of the Future. 4 (3): 223. doi:10.1358/dof.1979.004.03.1002424.
  3. ↑ Schurr PE, Day CE (January 1977). "Response to the hypobetalipoproteinemic agent adamantyloxyphenyl piperidine in hyperlipemic rats". Lipids. 12 (1): 22–28. doi:10.1007/BF02532967. PMID   189153.
  4. ↑ Day CE, Schurr PE, Heyd WE, Lednicer D (1976). "Biological activity of a hypobetalipoproteinemic agent". In Day DE (ed.). Advances in Experimental Medicine and Biology. Vol. 67. Springer US. pp. 231–249. doi:10.1007/978-1-4614-4618-7_14. ISBN   978-1-4757-9309-3. PMID   179296.
  5. ↑ Maxwell RE, Nawrocki JW, Uhlendorf PD (1978). "Effects of gemfibrozil (CI-719), gemcadiol (CI-720), clofibrate and U-41792 on cholesterol distribution in rat plasma fractions obtained by polyanion precipitation". Artery. 4 (4). Fulton, MI: 303–313.
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