155584-74-0

Usage

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 academic research and scientific papers

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.

Fragment based design of new H4 receptor-ligands with anti-inflammatory properties in vivo

Using a previously reported flexible alignment model we have designed, synthesized, and evaluated a series of compounds at the human histamine H 4 receptor (H4R) from which 2-(4-methyl-piperazin-l-yl)- quinoxaline (3) was identified as a new lead structure for H4R ligands. Exploration of the structure-activity relationship (SAR) of this scaffold led to the identification of 6,7-dichloro 3-(4-methylpiperazin-l-yl) quinoxalin-2(1H)-one (VUF 10214, 57) and 2-benzyl-3-(4-methyl-piperazin-l-yl) quinoxaline (VUF 10148, 20) as potent H4R ligands with nanomolar affinities. In vivo studies in the rat reveal that compound 57 has significant anti-inflammatory properties in the carrageenan-induced paw-edema model.