2- Naphthylacetic acid

C18H20O4 101743-90-2) see Methallenestril 6-methoxy-2-naphthylacetic acid (C13H12OJ 23981-47-7) see Naproxen... 

L. K. Wadhwa, P. D. Sharma, Glycolamide Esters of 6-Methoxy-2-naphthylacetic Acid as Potential Prodrugs-Physicochemical Properties, Chemical Stability and Enzymatic Hydrolysis , Int. J. Pharm. 1995, 118, 31-39. 

Nabumetone selectively inhibits COX-2. It is metabolised into 6-methoxy-2-naphthylacetic acid (MNA), that is a potent inhibitor of COX-2. It has no inhibitory effect on COX-1 which is responsible for prostaglandin synthesis in gastric mucosa, thereby minimising the risk of problems like ulcers and hypertension. After oral administration 80% of dose is excreted in the urine. Peak plasma concentration is reached after 2.5 to 4 hours. 

Mix 130g (0.48 mol) of the crude thiomorpholide with 270 ml of glacial acetic acid, 40 ml of concentrated sulphuric acid and 60 ml of water raise the temperature of the mixture carefully to the boiling point and reflux for 5 hours. Decant the solution from a little tarry matter into 2 litres of water and keep overnight. Collect the solid by suction filtration and wash it well with cold water. Digest the solid with a solution of 50 g of sodium hydroxide in 1 litre of water, filter and acidify the filtrate with hydrochloric acid filter off the crude 2-naphthylacetic acid, wash with water and dry. The yield of the crude acid, m.p. 137-140 °C, is 75 g (84%). Recrystallisation from benzene raises the... 

A solution of 27.8 kg of 2-naphthylacetic acid in 95 L of tetrahydrofuran is added, at a temperature below 20°C to a mixture of 27.5 L of tetrahydrofuran and 10.0 kg of lithium aluminum hydride. The mixture is cooled to 0°C and the following are then added slowly firstly 10 L of water, then a solution of 1.5 kg of sodium hydroxide in 10 L of water, and finally 30 L of water. The salts which separate out are washed with 160 L of tetrahydrofuran and then... 

The reaction with sulfur and morpholine can be applied to the preparation of aromatic acids containing polynuclear residues. Methyl 2-naph-thyl ketone refluxed for 16 h with a 50% excess of sulfur and morpholine furnishes a 90% yield of the thiomorpholide of 2-naphthylacetic acid, from which 2-naphthylacetic acid is obtained by refluxing for 5 h with aqueous sulfuric and acetic acid (yield 90%). 1-Acenaphthylacetic acid is prepared by heating 1-acetylacenaphthene with sulfur and ammonium sulfide at... 

Nabumetone. Nabumetone. 4-(6-mcthoxy-2-naphthyl)-2-butanone (Relafen), serves os a pmdnig to its aetive metabolite. 6-methoxy-2-naphthylacetic acid. Like the other aryla-cetic acid drugs, it is used in short- ur long-term management of RA and OA. It is available as tablets (500 and 750 mg), with a recommended. single daily dose of 1.000 mg. 

Carboxylic acids have also been masked as ketones and alcohols, which would require oxidation to convert to the active acid drugs. Nabumetone (61) is a nonaci-dic nonsteroidal anti-inflammatory prodrug (NSAID).39 After absorption, nabumetone undergoes extensive metabolism, the main circulating active form is 6-methoxy-2-naphthylacetic acid (62), a potent COX-2 inhibitor (Scheme 8). Since... 

All compounds of the test dataset are nonsteroidal anti-inflammatory drugs (NSAIDs) and are thus relatively similar in terms of their pharmacological properties (Fig. 18). The compounds are 1, acetylsalicylic acid 2, diclofenac 3, flufe-namic acid 4, flubiprofen 5, ibuprofen 6, indometacin 7, ketoprofen 8, meclofe-namic acid 9, mefenamic acid 10, naproxen 11, piroxicam 12, sulindac sulfide (active metabolite of sulindac) 13, tenoxicam 14, meloxicam 15, cgp 28238 16, DuP-697 17, L-745-337 18, 6-methoxy-2-naphthylacetic acid (active metabolite of nabumeton) 19, NS-389 20, SC 58125. 

Bosca, F., Canudas, N., Marin, M.L., and Miranda, M.A. (2002) A photophysical and photochemical study of 6-methoxy-2-naphthylacetic acid, the major metabolite of the phototoxic non-steroidal antiinflammatory drug nabumetone, Photochem. Photobiol., 71, 173-177. 

Nabumetone is absorbed rapidly and is converted in the liver to one or more active metabohtes, principally 6-methoxy-2-naphthylacetic acid, a potent nonselective inhibitor of COX. This metabolite, inactivated by (9-demethylation in the liver, is then conjugated before exaetion, and is eliminated with a half-life of about 24 hours. 

Sample preparation 0.5 mL Plasma -I- 2.5 pL 400 pg/mL 6-chloro-2-naphthylacetic acid in acetone, mix on a whirlmixer, add 6 mL n-hexane ethyl acetate 50 50, add 0.7 mL 1.5 M HCl, shake mechanically for 30 min, centrifuge at 1500 g for 10 min. mover organic layer and evaporate it to dryness at 37 under a stream of nitrogen. Dissolve residue in mobile phase, centrifuge, inject a 20 pL aliquot. 

Internal standard 6-chloro-2-naphthylacetic acid (6) Limit of detection 250 ng/mL... 

Mobile phase MeCN 50 mM NaH2P04 40 60, pH 5.2 (For the active metabolite, 6-meth-03gr-2-naphthylacetic acid, use MeCN 50 mM NaH2P04 30 70, pH 5.2.)... 

In a series of substituted 2-naphthylacetic acids, substitution in the 6-position led... 

Harrison IT, Lewis B, Nelson P, et al. Nonsteroidal anti-inflammatory agents. I. 6-Substituted 2-naphthylacetic acids. J Med Chem 1970 13 203-205. 

Mikami, E. Goto, T. Ohno, T. Matsumoto, H. Nishida, M. Simultaneous analysis of naproxen, nabumetone and its major metabolite 6-methoxy-2-naphthylacetic acid in pharmaceuticals and human urine by high-performance liquid chromatography. J. Pharm. Biomed. Anal. 2000,23 (5), 917-925. 

Turpeinen M, Hofmann U, Klein K, Murdter T, Schwab M, Zanger UM (2009) A predominate role of CYP1A2 for the metabolism of nabumetone to the active metabolite, 6-methoxy-2-naphthylacetic acid, in human liver microsomes. Drug Metab Dispos 37 1017-1024... 

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