66646-99-9

Basic information

• Product Name: Morpholine, 4-[3-(2-hydroxyphenyl)-1,3-dioxopropyl]-
• CAS NO: 66646-99-9
• Molecular Formula: C13H15NO4
• Molecular Weight: 249.266
• Mol File: 66646-99-9.mol

Chemical Properties

• CAS DataBase Reference: Morpholine, 4-[3-(2-hydroxyphenyl)-1,3-dioxopropyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Morpholine, 4-[3-(2-hydroxyphenyl)-1,3-dioxopropyl]-(66646-99-9)
• EPA Substance Registry System: Morpholine, 4-[3-(2-hydroxyphenyl)-1,3-dioxopropyl]-(66646-99-9)

Safety Data

• Hazardous Substances Data: 66646-99-9(Hazardous Substances Data)

Upstream product

• 1696-20-4 4-acetylmorpholine 
• 119-36-8 methyl salicylate 

Downstream Products

• 130735-56-7 2-(4-morpholinyl)-4H-1-benzopyran-4-one 

Relevant articles and documents

A cyclodehydration route to 2-aminochromones

Cyclodehydration of a series of salicylacetamides with triflic anhydride efficiently provided the corresponding 2-aminochromone. The use of polyphosphoric ester for this process was somewhat less effective.

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.