607742-69-8

Basic information

• Product Name: Sb-742457
• Synonyms: Gsk 742457;Sb 742457;Sb-742457;3-Phenylsulfonyl-8-(piperazin-1-yl)quinoline;SB 742457/GSK 742457;Quinoline, 3-(phenylsulfonyl)-8-(1-piperazinyl)-;3-(BENZENESULFONYL)-8-(PIPERAZIN-1-YL)QUINOLINE;SB742457:Intepirdine
• CAS NO: 607742-69-8
• Molecular Formula: C₁₉H₁₉N₃O₂S
• Molecular Weight: 353.444
• Product Categories: Inhibitors
• Mol File: 607742-69-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 608.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.292
• Solubility: insoluble in H2O; ≥17.65 mg/mL in DMSO; ≥2.13 mg/mL in EtOH with gentle warming and ultrasonic
• PKA: 8?+-.0.10(Predicted)
• CAS DataBase Reference: Sb-742457(CAS DataBase Reference)
• NIST Chemistry Reference: Sb-742457(607742-69-8)
• EPA Substance Registry System: Sb-742457(607742-69-8)

Safety Data

• Hazardous Substances Data: 607742-69-8(Hazardous Substances Data)

Usage

Description

SB-742457 is an orally bioavailable antagonist of the serotonin (5-HT) receptor subtype 5-HT6, characterized by its high affinity for the receptor (Ki = 1.4 nM). It also exhibits high affinity binding to other 5-HT receptors, including 5-HT1B, 5-HT2A, 5-HT2B, and 5-HT2C. SB-742457 effectively reduces 5-HT6 activation of Gs-mediated cAMP production in a concentration-dependent manner, with an EC50 value of 21 nM in NG108-15 neuroblastoma cells. In vivo, it has been shown to reverse cognitive deficits induced by scopolamine and age-induced impairments in spatial memory acquisition and retention in rats. Additionally, it has demonstrated a role in satiety and obesity management.

Uses

Used in Pharmaceutical Industry:
SB-742457 is used as a selective 5-HT6 receptor antagonist for improving cognitive function. Its ability to reverse cognitive deficits induced by scopolamine and age-induced impairments in spatial memory acquisition and retention makes it a promising candidate for the development of treatments for cognitive disorders and age-related cognitive decline.
Used in Obesity Management:
SB-742457 is used as a potential therapeutic agent for satiety and obesity management. Its demonstrated effect in reducing the number of licking bouts by 24% compared to control in rats trained to lick a glucose solution suggests that it may play a role in modulating appetite and promoting weight management.
Used in Research Applications:
SB-742457 is used as a research tool for studying the role of 5-HT6 receptors in various physiological and pathological processes. Its high affinity for multiple 5-HT receptors makes it a valuable compound for investigating the complex interactions between these receptors and their potential implications in various conditions, including cognitive disorders, obesity, and other related areas.

references

[1] aaron t. t. chuang, andrew foley, perdita l. pugh, david sunter, xin tong, ciaran regan, lee a. dawson, andrew d. medhurst, neil upton.5-ht6 receptor antagonist sb-742457 as a novel cognitive enhancing agent for alzheimer’s disease. alzheimer's & dementia: the journal of the alzheimer's association volume 2, issue 3, supplement, pages s631–s632, july 2006

Upstream product

• 1429304-29-9 8-chloro-3-(phenylsulfonyl)quinoline 
• 611-33-6 8-chloroquinoline 
• 607743-10-2 tert-butyl 4-[3-(phenylsulfonyl)quinolin-8-yl]piperazine-1-carboxylate 
• 847727-21-3 8-chloro-3-iodo-quinoline 
• 110-85-0 piperazine 
• 866782-60-7 8-fluoro-3-(phenylsulfonyl)quinoline 
• 607743-09-9 8-iodo-3-(phenylsulfonyl)quinoline 

Downstream Products

• 1608477-70-8 8-{4-[(4-fluorophenyl)sulfonyl]piperazin-1-yl}-3-(phenylsulfonyl)quinoline 
• 1608477-71-9 8-{4-[(2-fluorophenyl)sulfonyl]piperazin-1-yl}-3-(phenylsulfonyl)quinoline 
• 1578264-76-2 (¹¹C)LuPET 

Relevant articles and documents

A Class of Amide Ligands Enable Cu-Catalyzed Coupling of (Hetero)aryl Halides with Sulfinic Acid Salts under Mild Conditions

The amide derived from 4-hydroxy-l-proline and 2,6-dimethylaniline is a powerful ligand for Cu-catalyzed coupling of (hetero)aryl halides with sulfinic acid salts, allowing the formation of a wide range of (hetero)aryl sulfones from the corresponding (hetero)aryl halides at considerably low catalytic loadings. The coupling of (hetero)aryl iodides and sodium methanesulfinate proceeds at room temperature with only 0.5 mol % CuI and ligand, representing the first example for Cu-catalyzed arylation at both low catalytic loading and room temperature.

Palladium-catalyzed three-component diaryl sulfone synthesis exploiting the sulfur dioxide surrogate DABSO

SO(2) efficient: A three-component palladium-catalyzed coupling of aryl lithium compounds; sulfur dioxide (provided by the easy-to-handle solid surrogate, DABSO); and aryl, heteroaryl, and alkenyl (pseudo)halides yields a diverse library of sulfones. An electron-poor XantPhos-type ligand suppresses aryl-aryl exchange and is key to obtaining high yields.

A POLYMORPHIC FORM OF 3-PHENYLSULFONYL -8-PIPERAZIN-1-YL-QUINOLINE

This invention relates to a novel compound of 3-phenylsulfonyl -8-piperazin-1-yl-quinoline, to processes for its preparation, to compositions containing it and to its use in the treatment of CNS and other disorders.