61035-04-9

Basic information

• Product Name: 2-pyrrolidin-1-yl-4H-benzo[h]chromen-4-one
• Synonyms: 2-(pyrrolidin-1-yl)-4H-benzo[h]chromen-4-one; 4H-naphtho[1,2-b]pyran-4-one, 2-(1-pyrrolidinyl)-
• CAS NO: 61035-04-9
• Molecular Formula: C₁₇H₁₅NO₂
• Molecular Weight: 265.3065
• Mol File: 61035-04-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 429.7°C at 760 mmHg
• Flash Point: 213.7°C
• Density: 1.309g/cm³
• Vapor Pressure: 1.37E-07mmHg at 25°C
• Refractive Index: 1.692
• CAS DataBase Reference: 2-pyrrolidin-1-yl-4H-benzo[h]chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-pyrrolidin-1-yl-4H-benzo[h]chromen-4-one(61035-04-9)
• EPA Substance Registry System: 2-pyrrolidin-1-yl-4H-benzo[h]chromen-4-one(61035-04-9)

Safety Data

• Hazardous Substances Data: 61035-04-9(Hazardous Substances Data)

Upstream product

• 173210-13-4 4-Hydroxy-2H-naphtho<1,2-b>pyran-2-thione 
• 711-79-5 1-hydroxy-2-acetonaphthone 
• 503469-20-3 2-ethylsulfanylbenzo[h]chromen-4-one 
• 123-75-1 pyrrolidine 
• 503469-28-1 2-ethanesulfonylbenzo[h]chromen-4-one 

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.