273196-12-6

Basic information

• Product Name: 3-(2-NAPHTHALEN-2-YL-2-OXO-ETHYLIDENE)-3,4-DIHYDRO-1H-QUINOXALIN-2-ONE
• Synonyms: 3-(2-NAPHTHALEN-2-YL-2-OXO-ETHYLIDENE)-3,4-DIHYDRO-1H-QUINOXALIN-2-ONE;(3Z)-3-[2-(naphthalen-2-yl)-2-oxoethylidene]-1,2,3,4-tetrahydroquinoxalin-2-one
• CAS NO: 273196-12-6
• Molecular Formula: C20H14N2O2
• Molecular Weight: 314.34
• Mol File: 273196-12-6.mol

Chemical Properties

• Boiling Point: 557.4°C at 760 mmHg
• Flash Point: 210.2°C
• Appearance: /
• Density: 1.334g/cm³
• Vapor Pressure: 1.85E-12mmHg at 25°C
• Refractive Index: 1.733
• PKA: 10.35±0.20(Predicted)
• CAS DataBase Reference: 3-(2-NAPHTHALEN-2-YL-2-OXO-ETHYLIDENE)-3,4-DIHYDRO-1H-QUINOXALIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-NAPHTHALEN-2-YL-2-OXO-ETHYLIDENE)-3,4-DIHYDRO-1H-QUINOXALIN-2-ONE(273196-12-6)
• EPA Substance Registry System: 3-(2-NAPHTHALEN-2-YL-2-OXO-ETHYLIDENE)-3,4-DIHYDRO-1H-QUINOXALIN-2-ONE(273196-12-6)

Safety Data

• Hazardous Substances Data: 273196-12-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(2-NAPHTHALEN-2-YL-2-OXO-ETHYLIDENE)-3,4-DIHYDRO-1H-QUINOXALIN-2-ONE is used as a potential pharmaceutical agent for its possible anti-inflammatory, antioxidant, and anti-cancer activities. Its molecular structure suggests that it could be a candidate for the development of new drugs targeting various diseases and conditions.
Used in Research and Development:
In the field of scientific research, 3-(2-NAPHTHALEN-2-YL-2-OXO-ETHYLIDENE)-3,4-DIHYDRO-1H-QUINOXALIN-2-ONE serves as a subject for further studies to understand its properties, potential applications, and mechanisms of action. This may lead to the discovery of new therapeutic agents or the enhancement of existing ones.

InChI:InChI=1/C20H14N2O2/c23-19(15-10-9-13-5-1-2-6-14(13)11-15)12-18-20(24)22-17-8-4-3-7-16(17)21-18/h1-12,21H,(H,22,24)/b18-12-

Upstream product

• 105356-61-4 4-(naphthalen-2-yl)-2,4-dioxobutanoic acid 
• 95-54-5 1,2-diamino-benzene 
• 36983-38-7 ethyl 4-(naphthalen-2-yl)-2,4-dioxobutanoate 
• 93-08-3 methyl 2-naphthyl ketone 

Relevant articles and documents

Rational modification, synthesis and biological evaluation of 3,4-dihydroquinoxalin-2(1H)-one derivatives as potent and selective c-Jun N-terminal kinase 3 (JNK3) inhibitors

The c-Jun N-terminal kinase 3 (JNK3) plays key roles in a wide range of diseases, including neurodegeneration diseases, inflammation diseases, cancers, cardiovascular diseases, and metabolic disorders. Previously, we have identified a lead compound, (Z)-3

Microwave-assisted one-pot efficient synthesis of functionalized 2-oxo-2-phenylethylidenes-linked 2-oxobenzo[1, 4]oxazines and 2-oxoquino[1, 4]oxalines: Synthetic applications, antioxidant activity, SAR and cytotoxic studies

A microwave-assisted, environmentally benign green protocol for the synthesis of functionalized (Z)-3-(2-oxo-2-phenylethylidene)-3, 4-dihydro-2H-benzo[b][1, 4]oxazin-2-ones (11a-n) in excellent yields (upto 97%) and (Z)-3-(2-oxo-2-phenylethylidene)-3, 4-dihydroquinoxalin-2(1H)-ones (14a-h) (upto 96% yield) are reported. The practical applicability of developed methodology were also confirmed by the gram scale synthesis of 11a, 14c and 14e; synthesis of anticancer alkaloid Cephalandole A 16 (89% yield). All the synthesized compounds 11a-n, 14a-h and 16 were assessed for their in vitro antioxidant activities in DPPH radical scavenging and FRAP assay. In DPPH assay, compounds 11a, 14c and 14e, the most active compounds of the series, were found to show IC50 value of 10.20 ± 0.08 μg/mL, 9.89 ± 0.15 μg/mL and 8.97 ± 0.13 μg/mL, respectively in comparison with standard reference (ascorbic acid, IC50 = 4.57 μg/mL). Whereas, in FRAP antioxidant assay seven compounds (11c, 11e, 11i, 11k, 11l, 14d and 14h) displayed higher antioxidant activity in comparison to the reference standard BHT (C0.5FRAP = 546.2 μM). Moreover, the cytotoxic studies of the compounds 11a, 14c, 14e and 14h were found to be non-toxic in nature in 3T3 fibroblast cell lines using MTT assay.