155584-74-0

Basic information

• Product Name: VUF 10166
• Synonyms: 2-Chloro-3-(4-Methyl-1-piperazinyl)quinoxaline;VUF 10166;Quinoxaline, 2-chloro-3-(4-methyl-1-piperazinyl)-
• CAS NO: 155584-74-0
• Molecular Formula: C13H15ClN4
• Molecular Weight: 262.738
• EINECS: -0
• Product Categories: Inhibitors
• Mol File: 155584-74-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 389.6±42.0 °C(Predicted)
• Appearance: /
• Density: 1.279±0.06 g/cm3(Predicted)
• Solubility: ≥26.3 mg/mL in EtOH; insoluble in H2O; ≥38.8 mg/mL in DMSO
• PKA: 6.55±0.42(Predicted)
• CAS DataBase Reference: VUF 10166(CAS DataBase Reference)
• NIST Chemistry Reference: VUF 10166(155584-74-0)
• EPA Substance Registry System: VUF 10166(155584-74-0)

Safety Data

• Hazardous Substances Data: 155584-74-0(Hazardous Substances Data)

Usage

Description

VUF 10166 is a compound that acts as a 5-HT3 receptor antagonist, with partial agonist activity at 5-HT3A receptors at higher concentrations, and also functions as a histamine H4 receptor antagonist. It is a pharmaceutical agent with potential applications in various medical fields due to its ability to modulate specific receptor activities.

Uses

Used in Pharmaceutical Industry:
VUF 10166 is used as a 5-HT3 receptor antagonist for treating conditions related to serotonin dysregulation, such as nausea and vomiting caused by chemotherapy or radiation therapy. Its antagonist activity at 5-HT3 receptors can help alleviate these symptoms by blocking the action of serotonin on these receptors.
VUF 10166 is used as a partial agonist at 5-HT3A receptors at higher concentrations, which may have potential therapeutic applications in conditions where modulation of 5-HT3A receptor activity is beneficial.
VUF 10166 is used as a histamine H4 receptor antagonist, which may have implications in treating various inflammatory and allergic conditions, as well as other disorders where histamine H4 receptor modulation is involved.

Biological Activity

vuf10166 is a novel, potent and competitive antagonist for 5-ht3a receptor with ki of 0.04 nm, its affinity at 5-ht3ab receptor is significantly lower.

InChI:InChI=1S/C13H15ClN4/c1-17-6-8-18(9-7-17)13-12(14)15-10-4-2-3-5-11(10)16-13/h2-5H,6-9H2,1H3

Upstream product

• 109-01-3 1-methyl-piperazine 
• 2213-63-0 2,3-dichloroquinoxaline 
• 15804-19-0 quinoxaline-2,3-dione 
• 95-54-5 1,2-diamino-benzene 

Relevant articles and documents

Design and synthesis of quinoxaline-1,3,4-oxadiazole hybrid derivatives as potent inhibitors of the anti-apoptotic Bcl-2 protein

Quinoxaline is one of the privileged heterocyclic fragments for drug molecules. Quinoxaline anticancer drug candidates XK469 and CQS exhibit antiproliferative and proapoptotic properties against various cancers. Based on their chemical structures, we therefore synthesized a series of quinoxaline-1,3,4-oxadiazole hybrids and assessed their anticancer potential on human leukemia HL-60 cells. Although these hybrids exerted significant inhibition of HL-60 cell proliferation, they showed high cytotoxicity on human normal cells (WI-38). Utilizing information from molecular modelling of the hybrids to the anti-apoptotic Bcl-2 protein, we added substructures including phenyl, piperazine, piperidine, and morpholine rings to their frameworks. The designed quinoxaline-1,3,4-oxadiazole hybrid derivatives successfully induced apoptotic response on HL-60 cells with low toxicity on WI-38 cells. Furthermore, RT-PCR analysis demonstrated that these derivatives predominantly inhibit Bcl-2 expression. Our findings highlight the great potential for the development of synthetic quinoxaline-1,3,4-oxadiazole hybrid derivatives as proapoptotic anticancer agents.