U-41792

Antihyperlipidemic agent From Wikipedia, the free encyclopedia

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]

CAS Number
Quick facts Identifiers, CAS Number ...
U-41792
Identifiers
  • 1-[4-(1-adamantyloxy)phenyl]piperidine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H29NO
Molar mass311.469 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
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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 nitro group is then reduced and alkylated to give U-41792.[1]

References

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