915016-55-6

Basic information

• Product Name: methyl 4-(2-cyclopropylethoxy)benzoate
• Synonyms: methyl 4-(2-cyclopropylethoxy)benzoate
• CAS NO: 915016-55-6
• Molecular Weight: 220.268
• Mol File: 915016-55-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 4-(2-cyclopropylethoxy)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-(2-cyclopropylethoxy)benzoate(915016-55-6)
• EPA Substance Registry System: methyl 4-(2-cyclopropylethoxy)benzoate(915016-55-6)

Safety Data

• Hazardous Substances Data: 915016-55-6(Hazardous Substances Data)

Upstream product

• 2566-44-1 1-cyclopropylethanol 
• 99-76-3 methyl 4-hydroxylbenzoate 

Downstream Products

• 915016-54-5 4-(2-cyclopropylethoxy)benzoic acid 
• 915016-56-7 N-[4-(2-cyclopropylethoxy)benzoyl]glycine 
• 915011-07-3 4-(2-cyclopropylethoxy)-N-((Z)-2-(4-cyclopropylphenyl)-1-{[(2-hydroxyethyl)amino]carbonyl}vinyl)benzamide 
• 756478-85-0 p-(2-cyclopropylethoxy)benzoyl chloride 
• 1373823-19-8 4-(2-cyclopropylethoxy)-N-[8-methyl-3-(pyrrolidin-1-ylmethyl)quinolin-7-yl]benzamide 

Relevant articles and documents

Synthesis, structure-activity relationship, and pharmacological studies of novel melanin-concentrating hormone receptor 1 antagonists 3- aminomethylquinolines: Reducing human ether-a-go-go-related gene (hERG) associated liabilities

Recently, we discovered 3-aminomethylquinoline derivative 1, a selective, highly potent, centrally acting, and orally bioavailable human MCH receptor 1 (hMCHR1) antagonist, that inhibited food intake in F344 rats with diet-induced obesity (DIO). Subsequent investigation of 1 was discontinued because 1 showed potent hERG K+ channel inhibition in a patch-clamp study. To decrease hERG K+ channel inhibition, experiments with ligand-based drug designs based on 1 and a docking study were conducted. Replacement of the terminal p-fluorophenyl group with a cyclopropylmethoxy group, methyl group introduction on the benzylic carbon at the 3-position of the quinoline core, and employment of a [2-(acetylamino)ethyl]amino group as the amine portion eliminated hERG K+ channel inhibitory activity in a patch-clamp study, leading to the discovery of N-{3-[(1R)-1-{[2-(acetylamino)ethyl]amino} ethyl]-8-methylquinolin-7-yl}-4-(cyclopropylmethoxy)benzamide (R)-10h. The compound (R)-10h showed potent inhibitory activity against hMCHR1 and dose-dependently suppressed food intake in a 2-day study on DIO-F344 rats. Furthermore, practical chiral synthesis of (R)-10h was performed to determine the molecule's absolute configuration.

SUBSTITUTED ACRYLAMIDE DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

A pharmaceutical composition comprising a compound having Formula (I) or a pharmacologically acceptable salt thereof as an active ingredient: [wherein, R1 is, for example, a C6-C10 aryl group which may be substituted with one group or more than one group selected from substituent group α; R2 is, for example, a C6-C10 aryl group which may be substituted with one group or more than one group selected from substituent group α; and X is, for example, a hydroxyl group or a C1-C6 alkoxy group].