154447-35-5

Basic information

• Product Name: NU7026
• Synonyms: 2-(4-Morpholinyl)-4H-naphtho[1,2-b]pyran-4-one;LY 293646;4H-Naphtho[1,2-b]pyran-4-one, 2-(4-morpholinyl)-;2-(4-Morpholinyl)-4H-naphtho[1,2-b]pyran-4-one NU7026;2-MORPHOLINO-4H-BENZO[H]CHROMEN-4-ONE;NU7026, >=98%;2-(4-Morpholinyl)-4H-naphthol[1,2-b]pyran-4-one
• CAS NO: 154447-35-5
• Molecular Formula: C17H15NO3
• Molecular Weight: 281.31
• Product Categories: Inhibitors
• Mol File: 154447-35-5.mol

Chemical Properties

• Melting Point: 267-269 °C(Solv: methanol (67-56-1); water (7732-18-5))
• Boiling Point: 459.879°C at 760 mmHg
• Flash Point: 231.927°C
• Appearance: tan/solid
• Density: 1.330
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.673
• Storage Temp.: 2-8°C
• Solubility: DMSO: 3 mg/mL at 60 °C, soluble
• PKA: 0.49±0.20(Predicted)
• CAS DataBase Reference: NU7026(CAS DataBase Reference)
• NIST Chemistry Reference: NU7026(154447-35-5)
• EPA Substance Registry System: NU7026(154447-35-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 154447-35-5(Hazardous Substances Data)

Usage

Uses

Used in Cancer Research:
NU7026 is used as an antiproliferative agent for studying its effects on cancer cell growth and proliferation. It is particularly useful in understanding the role of DNA-PK in cancer development and progression.
Used in Colon Cancer Cell Studies:
In the field of colon cancer research, NU7026 is used as a DNA-PK inhibitor to pre-treat colon cancer cells in kinase inhibitor experiments. This helps researchers investigate the compound's influence on cell behavior and its potential as a therapeutic agent for colon cancer treatment.
Used in Fertility Studies:
NU7026 is utilized in experiments involving the treatment of zygotes with visible pronuclei post 20 hours of human chorionic gonadotropin (hCG) administration. This application aids in understanding the compound's impact on early-stage embryonic development and its potential implications for fertility treatments.
Used in Hepatotoxicity Studies:
In the context of hepatotoxicity research, NU7026 is used to determine its influence on the cytotoxicity of dibenzo[def,p]chrysene on HepG2 cells. This application helps researchers explore the compound's potential role in mitigating or exacerbating liver cell damage caused by toxic substances.
Overall, NU7026 is a versatile compound with applications in various fields, including cancer research, fertility studies, and hepatotoxicity investigations. Its use as a DNA-PK inhibitor allows researchers to explore its potential therapeutic effects and better understand the underlying mechanisms of various diseases and conditions.

Biological Activity

ATP-competitive inhibitor of DNA-dependent protein kinase (DNA-PK). Displays selectivity over other PIKK family enzymes (IC 50 values are 0.23, 13.0, > 100 and > 100 μ M for DNA-PK, PI3K, ATM and ATR respectively). Radiosensitizes both proliferating and quiescent mouse embryonic fibroblast cells to IR and inhibits DSB repair.

Biochem/physiol Actions

Cell permeable, small molecule benzochromenone inhibitor of DNA-PK (DNA dependent protein kinase).

InChI:InChI=1/C17H15NO3/c19-15-11-16(18-7-9-20-10-8-18)21-17-13-4-2-1-3-12(13)5-6-14(15)17/h1-6,11H,7-10H2

Upstream product

• 37714-64-0 3-(4-Morpholinyl)-3-oxopropansaeure-ethylester 
• 90-15-3 α-naphthol 
• 503469-16-7 1-(1-hydroxynaphth-2-yl)-3-(morpholin-4-yl)-propane-1,3-dione 
• 1696-20-4 4-acetylmorpholine 
• 948-03-8 1-hydroxy-naphthalene-2-carboxylic acid methyl ester 

Relevant articles and documents

Selective benzopyranone and pyrimido[2,1-α]isoquinolin-4-one inhibitors of DNA-dependent protein kinase: Synthesis, structure-activity studies, and radiosensitization of a human tumor cell line in vitro

A diverse range of chromen-2-one, chromen-4-one and pyrimidoisoquinolin-4- one derivatives was synthesized and evaluated for inhibitory activity against the DNA repair enzyme DNA-dependent protein kinase (DNA-PK), with a view to elucidating structure-activity relationships for potency and kinase selectivity. DNA-PK inhibitory activity varied widely over the series of compounds evaluated (IC50 values ranged from 0.19 to >10 μM), with excellent activity being observed for the 7,8-benzochromen-4-one and pyrimido[2,1-a] isoquinolin-4-one templates. By contrast, inhibitors based on the benzochromen-2-one (coumarin) or 2-aryl-7,8-benzochromen-4-one (flavone) scaffolds were less potent. Crucially, these studies revealed a very constrained structure-activity relationship at the 2-position of the benzopyranone and pyrimido[2,1-a]-isoquinolin-4-one pharmacophore, with only a 2-morpholino or 2-(2′-methylmorpholino) group being tolerated at this position. More detailed biological studies conducted with the most potent inhibitor NU7163 (48; IC50 = 0.19 μM) demonstrated ATP-competitive DNA-PK inhibition, with a Ki value of 24 nM, and 48 exhibited selectivity for DNA-PK compared with the related enzymes ATM, ATR, mTOR, and PI 3-K (p110alpha). Compound 48 sensitized the HeLa human tumor cell line to the cytotoxic effects of ionizing radiation in vitro, a dose modification factor of 2.3 at 10% survival being observed with an inhibitor concentration of 5 μM. This study identified these structural classes as novel DNA-PK inhibitors and delineated initial structure-activity relationships against DNA-PK.

Pyran derivatives XX. 2-Aminochromone benzo-fused derivatives with antiproliferative properties

The N-substituted 2-aminochromones 1 and their benzo-fused derivatives 2-4 described herein were mostly prepared by treating the corresponding (methylthio) derivatives 10-13 with an excess of the proper amines. Only the morpholino derivatives 3d and 4c we