36866-05-4

Basic information

• Product Name: 2,9-dihydroxypyrido[1,2-a]pyrimidin-4-one
• Synonyms: 2,9-dihydroxypyrido[1,2-a]pyrimidin-4-one
• CAS NO: 36866-05-4
• Molecular Formula: C₈H₆N₂O₃
• Molecular Weight: 178
• Mol File: 36866-05-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,9-dihydroxypyrido[1,2-a]pyrimidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,9-dihydroxypyrido[1,2-a]pyrimidin-4-one(36866-05-4)
• EPA Substance Registry System: 2,9-dihydroxypyrido[1,2-a]pyrimidin-4-one(36866-05-4)

Safety Data

• Hazardous Substances Data: 36866-05-4(Hazardous Substances Data)

Upstream product

• 16867-03-1 2-amino-3-hydroxypyridine 
• 15781-70-1 malonic acid bis-(2,4,6-trichloro-phenyl) ester 
• 105-53-3 diethyl malonate 

Downstream Products

• 912824-68-1 2-chloro-9-hydroxypyrido[1,2-a]pyrimidin-4-one 

Relevant articles and documents

Quinolinone and pyridopyrimidinone inhibitors of DNA-dependent protein kinase

8-Substituted 2-morpholin-4-yl-quinolin-4-ones and 9-substituted 2-morpholin-4-yl-pyrido[1,2-a]pyrimidin-4-ones with selected aryl and heteroaryl groups as the substituent have been synthesised as potential inhibitors of DNA-dependent protein kinase. A multiple-parallel approach, employing Suzuki cross-coupling methodology, was utilised in the preparation of 8-substituted 2-morpholin-4-yl-quinolin-4-ones. For this purpose 8-bromo-2-morpholin-4-yl- quinolin-4-one was required as an intermediate. This compound was obtained by adapting a literature route in which thermal cyclocondensation of (2-bromoanilino)-morpholin-4-yl-5-methylene-2,2-dimethyl[1,3]dioxane-4,6-dione afforded 8-bromo-2-morpholin-4-yl-quinolin-4-one. A multiple-parallel approach, employing Suzuki cross-coupling methodology, was also utilised to prepare 9-substituted 2-morpholin-4-yl-pyrido[1,2-a]pyrimidin-4-ones using 9-hydroxy-2-morpholin-4-yl-pyrido[1,2-a]pyrimidin-4-one O- trifluoromethanesulfonate as an intermediate. 8-Substituted 2-morpholin-4-yl- quinolin-4-ones and 9-substituted 2-morpholin-4-yl-pyrido[1,2-a]pyrimidin-4-ones were both inhibitors of DNA-dependent protein kinase. When the substituent was dibenzothiophen-4-yl, dibenzofuran-4-yl or biphen-3-yl, IC50 values in the low nanomolar range were observed. Interestingly, the pyridopyrimidinones and quinolinones were essentially equipotent with the corresponding 8-substituted 2-morpholin-4-yl-chromen-4-ones previously reported (I. R. Hardcastle, X. Cockcroft, N. J. Curtin, M. Desage El-Murr, J. J. J. Leahy, M. Stockley, B. T. Golding, L. Rigoreau, C. Richardson, G. C. M. Smith and R. J. Griffin, J. Med. Chem., 2005, 48, 7829-7846). The Royal Society of Chemistry.