Chemistry:U-41792
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
- ↑ 1.0 1.1 "Hypobetalipoproteinemic agents. 2. Compounds related to 4-(1-adamantyloxy)aniline". Journal of Medicinal Chemistry 22 (1): 69–77. January 1979. doi:10.1021/jm00187a016. PMID 218007.
- ↑ "U-41792". Drugs of the Future 4 (3): 223. 1979. doi:10.1358/dof.1979.004.03.1002424.
- ↑ "Response to the hypobetalipoproteinemic agent adamantyloxyphenyl piperidine in hyperlipemic rats". Lipids 12 (1): 22–28. January 1977. doi:10.1007/BF02532967. PMID 189153.
- ↑ "Biological activity of a hypobetalipoproteinemic agent". Advances in Experimental Medicine and Biology. 67. Springer US. 1976. pp. 231–249. doi:10.1007/978-1-4614-4618-7_14. ISBN 978-1-4757-9309-3. http://link.springer.com/10.1007/978-1-4614-4618-7_14.
- ↑ "Effects of gemfibrozil (CI-719), gemcadiol (CI-720), clofibrate and U-41792 on cholesterol distribution in rat plasma fractions obtained by polyanion precipitation.". Artery (Fulton, MI) 4 (4): 303–313. 1978. https://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=PASCAL7950132812.
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