1176327-37-9

Basic information

• Product Name: 2-(4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate
• Synonyms: 2-(4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate
• CAS NO: 1176327-37-9
• Molecular Weight: 346.404
• Mol File: 1176327-37-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-(4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate(1176327-37-9)
• EPA Substance Registry System: 2-(4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate(1176327-37-9)

Safety Data

• Hazardous Substances Data: 1176327-37-9(Hazardous Substances Data)

Upstream product

• 1361061-39-3 3-[4-(2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)phenoxy]propanoic acid 
• 1361061-36-0 C₁₃H₁₈O₄ 
• 1232866-84-0 C₁₈H₁₈O₄ 
• 204971-39-1 3-[4-(2-hydroxyethyl)phenoxy]propanoic acid 
• 1176327-35-7 methyl (4,4-dimethoxy-3,4-dihydro-2H-chromen-6-yl)acetate 
• 145760-37-8 methyl (4-oxo-3,4-dihydro-2H-chromen-6-yl)acetate 
• 1176327-34-6 Methyl [4-(3-chloro-3-oxopropoxy)phenyl]acetate 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 1176327-36-8 6-(2-hydroxyethyl)-2,3-dihydro-4H-chromen-4-one 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1176326-78-5 6-(2-{4-[4-bromo-3-(2-methoxyethoxy)benzyl]piperidin-1-yl}ethyl)-2,3-dihydro-4H-chromen-4-one benzenesulfonate 
• 1265463-60-2 6-{2-[4-(4-Bromo-3-hydroxybenzyl)piperidin-1-yl]ethyl}-3-hydroxy-2,3-dihydro-4H-chromen-4-one 
• 1265463-64-6 6-(2-{4-[4-Bromo-3-(2-methoxyethoxy)benzyl]piperidin-1-yl}ethyl)-4H-chromen-4-one 
• 1265463-72-6 6-{2-[4-(4-Bromo-3-hydroxybenzyl)piperidin-1-yl]ethyl}-4H-chromen-4-one 
• 1265463-78-2 6-(2-{4-[4-Bromo-3-(2-methoxyethoxy)benzyl]piperidin-1-yl}-1-hydroxyethyl)-2,3-dihydro-4H-chromen-4-one 
• 1265464-49-0 tert-Butyl [2-bromo-5-({1-[2-(3-hydroxy-4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl]piperidin-4-yl}methyl)phenoxy]acetate 
• 1265464-60-5 2-(3-Hydroxy-4-oxo-3,4-dihydro-2H-chromen-6-yl)ethyl 4-methylbenzenesulfonate 
• 1265464-62-7 2-(3-Hydroxy-4-oxo-4H-chromen-6-yl)ethyl 4-methylbenzenesulfonate 
• 1265464-41-2 C₂₇H₃₆BrNO₆ 
• 1265463-58-8 6-(2-{4-[4-bromo-3-(2-hydroxyethoxy)benzyl]piperidin-1-yl}ethyl)-3-hydroxy-2,3-dihydro-4H-chromen-4-one 
• 1265463-92-0 6-{2-[4-(4-Bromo-3-hydroxybenzyl)piperidin-1-yl]ethyl}-3,4-dihydro-2H-chromen-4-ol 
• 1176326-84-3 6-(2-{4-[3-(2-methoxyethoxy)-4-methylbenzyl]piperidin-1-yl}ethyl)-2,3-dihydro-4H-chromen-4-one 
• 1176326-91-2 6-(2-{4-[3-bromo-5-(2-methoxyethoxy)benzyl]piperidin-1-yl}ethyl)-2,3-dihydro-4H-chromen-4-one 
• 1265463-48-6 6-(2-{4-[4-bromo-3-(2-methoxyethoxy)benzyl]piperidin-1-yl}ethyl)-3,4-dihydro-2H-chromen-4-ol 

Relevant articles and documents

Discovery of DSP-1053, a novel benzylpiperidine derivative with potent serotonin transporter inhibitory activity and partial 5-HT1A receptor agonistic activity

We have previously shown that SMP-304, a serotonin uptake inhibitor with weak 5-HT1A partial agonistic activity, may act under high serotonin levels as a 5-HT1A antagonist that improves the onset of paroxetine in the rat swimming test. However, SMP-304 is mostly metabolized by CYP2D6, indicating limited efficacy among individuals and increased side effects. To reduce CYP2D6 metabolic contribution and enhance SERT/5-HT1A binding affinity, we carried out a series of substitutions at the bromine atom in the left part of the benzene ring of SMP-304 and replaced the right part of SMP-304 with a chroman-4-one. This optimization work led to the identification of the antidepressant candidate DSP-1053 as a potent SERT inhibitor with partial 5-HT1A receptor agonistic activity. DSP-1053 showed low CYP2D6 metabolic contribution and a robust increase in serotonin levels in the rat frontal cortex.

BENZYL PIPERIDINE COMPOUND

Provided is a new serotonin-reuptake inhibitor that exhibits affinity for serotonin-1A receptors. Said serotonin-reuptake inhibitor is a compound represented by formula (1) or a pharmacologically acceptable salt thereof. In the formula, R1 represents a hydrogen atom, a 2-hydroxyethyl group, or a 2-methoxyethyl group. R2 represents one of the following bonded to a methylene group which is bonded to a piperidine ring: a chlorine atom bonded in a p-position; a bromine atom bonded in a p-position; a methyl group bonded in a p-position; a chlorine atom bonded in an m-position; or a bromine atom bonded in an m-position. Either Y1 represents a hydrogen atom and Y2 represents a hydrogen atom or a hydroxyl group, or Y1 and Y2 together represent an oxo group. Z represents a group represented by one of the following formulas: formula (3-1-1), formula (3-1-2), formula (3-2-1), formula (3-2-2), formula (3-3-1), formula (3-3-2), formula (3-4-1), or formula (3-4-2). However, if R1 represents a 2-hydroxyethyl group or a 2-methoxyethyl group and Y1 and Y2 both simultaneously represent hydrogen atoms, then Z represents a group represented by one of the following formulas: formula (3-1-2), formula (3-2-1), formula (3-2-2), formula (3-3-1), formula (3-3-2), formula (3-4-1), or formula (3-4-2).