Nabumetone anti-inflammatory agent

Metabolic pathways rarely lead to breaking a carbon-carbon bond however, there are exceptions such as the conversion of the prodrug nabumetone to an active nonsteroidal anti-inflammatory agent as shown in Figure 4.84 (153). Although the mechanism of this conversion is unknown, if oxidation leads to two adjacent carbonyl groups it weakens the carbon-carbon bond and further oxidation leads the rupture of this bond. 

These studies have been extended and confirmed with A-monosubsti-tuted and A, A-di substituted carbamoylmethyl esters of 6-methoxy-2-naph-thylacetic acid [38], This compound, a close analogue of naproxen (8.26), is the active metabolite of the anti-inflammatory agent nabumetone. The A-substituents investigated were mostly lower alkyl and oxygenated alkyl groups. The compounds were quite stable in buffer under physiological... 

Nabumetone Relafen Effective as analgesic/anti-inflammatory agent with fewer side effects than most NSAIDs. 

Problem 23,28 Nabumetone is a pain reliever and anti-inflammatory agent sold under the brand name of Relafen. 

Nabumetone is an anti-inflammatory agent with the following structure ... 

Other examples for which homogeneously catalyzed Heck reactions have been exploited toward an industrial production include the preparation of the fragrance Lihal developed by Givaudan, the synthesis of the nonsteroidal anti-inflammatory drug Nabumeton by Hoechst-Celanese, ° and the synthesis of the sunscreen agent 2-ethylhexyl p-methoxy-cinnamate (EHMC) by Hoechst AG and other companies (Scheme 6). Noteworthy, Nabumeton is obtained in one step via coupling and domino isomerization reaction of 2-bromo-6-methoxynaphthalene with 3-buten-2-ol. ° ... 

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