87901-81-3

Usage

Uses

Used in Pharmaceutical Industry:
(6-METHOXY-1-NAPHTHYL)ACETIC ACID is used as an intermediate in the synthesis of various pharmaceuticals for its potential anti-inflammatory and analgesic properties. It aids in the development of new drugs for the treatment of pain and inflammation.
Used in Agrochemical Industry:
(6-METHOXY-1-NAPHTHYL)ACETIC ACID is used as an intermediate in the production of agrochemicals, contributing to the development of compounds that can enhance crop protection and yield.
Used in Synthesis of Novel Bioactive Compounds:
(6-METHOXY-1-NAPHTHYL)ACETIC ACID is utilized as a starting material in the synthesis of novel bioactive compounds, exploring its potential applications in various fields beyond pain and inflammation management.

InChI:InChI=1/C13H12O3/c1-16-11-5-6-12-9(7-11)3-2-4-10(12)8-13(14)15/h2-7H,8H2,1H3,(H,14,15)

Upstream product

• 105-36-2 ethyl bromoacetate 
• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 
• 40154-02-7 2-(6-methoxy-3,4-dihydro-naphthalen-1-yl)-acetic acid ethyl ester 

Downstream Products

• 18705-35-6 (6-hydroxy-[1]naphthyl)-acetic acid 
• 87901-83-5 (E)-2-(6-Methoxy-naphthalen-1-yl)-3-phenyl-acrylic acid methyl ester 
• 87901-80-2 (E)-2-(6-Methoxy-naphthalen-1-yl)-3-phenyl-acrylic acid 

Relevant academic research and scientific papers

Microsomal activation of dibenzo[def,mno]chrysene (anthanthrene), a hexacyclic aromatic hydrocarbon without a bay-region, to mutagenic metabolites

Metabolically formed dihydrodiol epoxides in the bay-region of polycyclic aromatic hydrocarbons are thought to be responsible for the genotoxic properties of these environmental pollutants. The hexacyclic aromatic hydrocarbon dibenzo[def,mno]chrysene (anthanthrene), although lacking this structural feature, was found to exhibit considerable bacterial mutagenicity in histidine-dependent strains TA97, TA98, TA100, and TA104 of S. typhimurium in the range of 18-40 his+-revertant colonies/nmol after metabolic activation with the hepatic postmitochondrial fraction of Sprague-Dawley rats treated with Aroclor 1254. This mutagenic effect amounted to 44-84% of the values determined with benzo[a]pyrene under the same conditions. The specific mutagenicity of anthanthrene in strain TA100 obtained with the cell fraction of untreated animals was 6 his+-revertant colonies/nmol and increased 2.7-fold after treatment with phenobarbital and 4.5-fold after treatment with 3-methylcholanthrene. To elucidate the metabolic pathways leading to genotoxic metabolites, the microsomal biotransformation of anthanthrene was investigated. A combination of chromatographic, spectroscopic, and biochemical methods allowed the identification of the trans-4,5-dihydrodiol, 4,5-oxide, 4,5-, 1,6-, 3,6-, and 6,12-quinones, and 1- and 3-phenols. Furthermore, two diphenols derived from the 3-phenol, possibly the 3,6 and 3,9 positional isomers, as well as two phenol dihydrodiols were isolated. Three pathways of microsomal biotransformation of anthanthrene could be distinguished: The K-region metabolites are formed via pathway I dominated by monooxygenases of the P450 1B subfamily. On pathway II the polynuclear quinones of anthanthrene are formed. Pathway III is preferentially catalyzed by monooxygenases of the P450 1A subfamily and leads to the mono- and diphenols of anthanthrene. The K-region oxide and the 3-phenol are the only metabolites of anthanthrene with strong intrinsic mutagenicity, qualifying them as ultimate mutagens or their precursors. From the intrinsic mutagenicity of these two metabolites and their metabolic formation, the maximal mutagenic effect was calculated. This demonstrates the dominating role of pathway III in the mutagenicity of anthanthrene under conditions where it exhibits the strongest bacterial mutagenicity. platt@ mail.uni-mainz.de.

Intramolecular Diels-Alder Reactions. 4. Additions to Naphthalene

N-Methyl-N-2-propynyl-1-naphthalenecarboxamide, N-methyl-N-2-propynyl-1-naphthaleneacetamide, and N-methyl-N-3-butynyl-1-naphthalenecarboxamide undergo intramolecular Diels-Alder reactions at 190 deg C, 250 deg C, and 270 deg C to give lactams 1, 6, and 9, respectively.The cyclization temperatures are higher by 80-120 deg C as compared to those of the corresponding anthracene derivatives.Elaboration of lactam 6 gave the trans-4a-aryldecahydroisoquinoline derivative 7a which, as the (-) isomer, was shown to have the same absolute stereochemistry as morphine.