55686-32-3

Basic information

• Product Name: 3-PIPERAZIN-1-YL-1H-QUINOXALIN-2-ONE
• Synonyms: 3-PIPERAZIN-1-YL-1H-QUINOXALIN-2-ONE;3-(Piperazin-1-yl)quinoxalin-2(1H)-one;3-(1-piperazinyl)-2(1H)-Quinoxalinone
• CAS NO: 55686-32-3
• Molecular Formula: C12H14N4O
• Molecular Weight: 230.26576
• Mol File: 55686-32-3.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-PIPERAZIN-1-YL-1H-QUINOXALIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PIPERAZIN-1-YL-1H-QUINOXALIN-2-ONE(55686-32-3)
• EPA Substance Registry System: 3-PIPERAZIN-1-YL-1H-QUINOXALIN-2-ONE(55686-32-3)

Safety Data

• Hazardous Substances Data: 55686-32-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 24, p. 93, 1981 DOI: 10.1021/jm00133a019

Upstream product

• 110-85-0 piperazine 
• 15804-19-0 quinoxaline-2,3-dione 
• 164670-46-6 2-chloro-3-(piperazin-1-yl)quinoxaline 
• 95-54-5 1,2-diamino-benzene 
• 2213-63-0 2,3-dichloroquinoxaline 

Relevant articles and documents

New Series of VEGFR-2 Inhibitors and Apoptosis Enhancers: Design, Synthesis and Biological Evaluation

Background: Cancer is still a major world health threat, causing a high rate of mortality. VEGFR-2 inhibitor anticancer agents are of great significance. However, they showed some serious side effects. Purpose: To discover new effective and safer anticancer agents, a new series of piperazinylquinoxaline-based derivatives was designed and synthesized on the basis of the pharmacophoric features of VEGFR-2 inhibitor drugs. Methods: The new candidates were evaluated against A549 lung cancer cells, HepG-2 hepatoma cells, Caco-2 colon cancer cells, MDA breast cancer cells, and VEGFR-2 kinase. Moreover, cell cycle kinetics and apoptosis rates were studied in HepG-2 cells treated with compound 11, which was the most promising candidate. Results: The new derivatives revealed better antitumor results (IC50 from 6.48 to 38.58 μM) against the aforementioned cancer cell lines than sorafenib. Also, the new candidates showed VEGFR-2 inhibition with IC50 values ranging from 0.19 to 0.60 μM compared to 0.08 μM for sorafenib. Compound 11, meanwhile, showed IC50 values equal to 10.61, 9.52, 12.45, 11.52, and 0.19 μM against the cancer cell lines and VEGFR-2, respectively. Moreover, compound 11 raised the apoptosis rate in HepG-2 cells from 5% to 44% and caused 4, 2.3, and 3-fold increases in BAX/Bcl-2 ratio, caspase-3 level, and P53 expression, respectively, compared to control untreated cells. Finally, the new derivatives displayed the correct binding mode into VEGFR-2 kinase pocket, giving interactions with the essential residues. Conclusion: This work suggests that compound 11 is a very significant anticancer candidate, and piperazinylquinoxaline is an important scaffold in the development of new potential effective and safer VEGFR-2 inhibitor agents.