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Usage

Uses

Used in Pharmaceutical Industry:
1-Naphthalenecarboxylicacid, 4-ethylis used as a key intermediate in the synthesis of antimalarial compounds. Its unique structure allows for the development of drugs that can effectively target and combat malaria-causing parasites, providing a valuable contribution to the treatment and prevention of this widespread disease.
Used in Agrochemical Industry:
1-Naphthalenecarboxylicacid, 4-ethylalso exhibits plant-growth activity, making it a potential candidate for use in the development of agrochemicals and plant growth regulators. By modulating plant growth and development, 1-Naphthalenecarboxylicacid, 4-ethyl- can contribute to improved crop yields and overall agricultural productivity.

InChI:InChI=1/C13H12O2/c1-2-9-7-8-12(13(14)15)11-6-4-3-5-10(9)11/h3-8H,2H2,1H3,(H,14,15)

Upstream product

• 100975-96-0 acetic acid-(4-ethyl-[1]naphthylmethyl ester) 
• 67668-17-1 1-bromo-4-ethylnaphthalene 
• 63051-75-2 1-ethyl-4-chloromethyl-naphthalene 
• 1127-76-0 1-ethylnapthelene 
• 824430-38-8 N,N-diphenyl-4-ethyl-1-naphthalenecarboxamide 
• 108368-96-3 (4-ethylnaphthalen-1-yl)methanol 
• 463-72-9 carbamic chloride 

Downstream Products

• 108368-96-3 (4-ethylnaphthalen-1-yl)methanol 
• 63051-75-2 1-ethyl-4-chloromethyl-naphthalene 
• 1349176-09-5 5-(4-ethyl-1-naphthoylamino)-1,3,4-thiadiazole-2-sulfonamide 
• 824959-83-3 JWH-213 
• 824959-81-1 JWH-210 
• 824430-39-9 4-ethyl-1-naphthoyl chloride 

Relevant academic research and scientific papers

Regioselective synthesis of alkylarenes by two-step ipso-substitution of aromatic dicarboxylic acids

A strategy for the regioselective alkylation of arenes was developed, starting from commercially available and inexpensive terephthalic acid or naphthalene-1,4-dicarboxylic acid. The method entails a formal ipso-substitution of the carboxylate groups by a sequence of reductive alkylation under Birch conditions and subsequent acid-mediated rearomatization with loss of carbon monoxide and carbon dioxide. More than 20 different arenes with various side-chains were synthesized. With naphthalene-1,4-dicarboxylic acid as starting material, we were able to control the degree of alkylation by choosing the appropriate electrophile in the Birch reduction. Thus, bisalkylated naphthalenes and naphthoic acids became available chemoselectively. All reactions afforded a single regioisomer exclusively in high yields. Overall, aromatic dicarboxylic acids are suitable substrates for a two-step ipso-substitution that allows the selective synthesis of alkylated benzenes and naphthalenes.

Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB1 and CB2 receptors: Steric and electronic effects of naphthoyl substituents. New highly selective CB2 receptor agonists

The synthesis and pharmacology of 47 1-alkyl-3-(1-naphthoyl)indoles (R = C3H7 and C5H11, R′ = H and CH3) is described. Naphthoyl substituents include 4- and 7-alkyl groups, plus 2, 4, 6, and 7-methoxy groups. Three of these compounds are highly selective CB2 receptor agonists. In an effort to improve indole-based CB2 cannabinoid receptor ligands and also to develop SAR for both the CB1 and CB2 receptors, 47 indole derivatives were prepared and their CB1 and CB2 receptor affinities were determined. The indole derivatives include 1-propyl- and 1-pentyl-3-(1- naphthoyl)indoles both with and without a 2-methyl substituent. Naphthoyl substituents include 4- and 7-alkyl groups as well as 2-, 4-, 6-, 7-methoxy and 4-ethoxy groups. The effects of these substituents on receptor affinities are discussed and structure-activity relationships are presented. In the course of this work three new highly selective CB2 receptor agonists were identified, 1-propyl-3-(4-methyl-1-naphthoylindole (JWH-120), 1-propyl-2-methyl-3-(6-methoxy-1-naphthoylindole (JWH-151), and 1-pentyl-3-(2-methoxy-1-naphthoylindole (JWH-267). GTPγS assays indicated that JWH-151 is a full agonist at CB2, while JWH-120 and JWH-267 are partial agonists. Molecular modeling and receptor docking studies were carried out on a set of 3-(4-propyl-1-naphthoyl)indoles, a set of 3-(6-methoxy-1- naphthoyl)indoles and the pair of N-pentyl-3-(2-methoxy-1-naphthoyl)indoles. Docking studies indicated that the CB1 receptor affinities of these compounds were consistent with their aromatic stacking interactions in the aromatic microdomain of the CB1 receptor.

CB2-selective cannabinoid analogues

Cannabinoid analogues that exhibit specificity for the CB2 cannabinoid receptor are provided. The analogues are 1-methoxy-, 1-deoxy-11-hydroxy- and 11-hydroxy-1-methoxy-Δ8-tetrahydrocannabinols and 1-alkyl-3(1-naphthoyl)indoles. The compounds are useful for the treatment of pain (especially pain resulting from inflammation) and cancer (especially glioma tumors).