119671-47-5

Basic information

• Product Name: 2-CHLORO-6-MORPHOLINOPYRAN-4-ONE
• Synonyms: 2-CHLORO-6-MORPHOLINOPYRAN-4-ONE;2-chloro-6-morpholin-4-ylpyran-4-one
• CAS NO: 119671-47-5
• Molecular Formula: C₉H₁₀ClNO₃
• Molecular Weight: 215.6336
• EINECS: -0
• Mol File: 119671-47-5.mol

Chemical Properties

• Boiling Point: 373.2±42.0 °C(Predicted)
• Appearance: /
• Density: 1.39±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly)
• PKA: 0.05±0.20(Predicted)
• CAS DataBase Reference: 2-CHLORO-6-MORPHOLINOPYRAN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-6-MORPHOLINOPYRAN-4-ONE(119671-47-5)
• EPA Substance Registry System: 2-CHLORO-6-MORPHOLINOPYRAN-4-ONE(119671-47-5)

Safety Data

• Hazardous Substances Data: 119671-47-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
2-Chloro-6-morpholinopyran-4-one is used as a research compound for its potential as a DNA-dependent protein kinase (DNA-PK) inhibitor and Ataxia Telangiectasia Mutated (ATM) kinase inhibitor. Its ability to inhibit these kinases makes it a valuable tool in studying the role of these enzymes in DNA repair and other biological processes.
Used in Cancer Therapy Development:
In the field of oncology, 2-chloro-6-morpholinopyran-4-one is being investigated for its potential use as a therapeutic agent in cancer treatment. Its inhibitory effects on DNA-PK and ATM kinases may help in targeting cancer cells with high genomic instability, thereby enhancing the effectiveness of radiotherapy and chemotherapy.
Used in Radioprotection:
Due to its inhibitory effects on DNA repair mechanisms, 2-chloro-6-morpholinopyran-4-one may also have applications in radioprotection. By inhibiting the DNA repair enzymes, it could potentially protect normal cells from the damaging effects of radiation while leaving cancer cells more susceptible to radiation-induced damage.
Used in Neurodegenerative Disease Research:
Given the involvement of DNA repair mechanisms in neurodegenerative diseases, 2-chloro-6-morpholinopyran-4-one may also be explored for its potential role in the treatment or management of such conditions. Its ability to modulate DNA repair pathways could provide insights into the development of therapeutic strategies for diseases like Alzheimer's and Parkinson's.

Upstream product

• 85839-49-2 4,4-dichloro-1-(morpholin-4-yl)but-3-ene-1,2-dione 
• 81189-95-9 4-chloro-4-(2,2,2-trichloroethyl)-oxetan-2-one 

Downstream Products

• 587871-26-9 2-(4-morpholinyl)-6-(1-thianthrenyl)-4H-pyran-4-one 
• 587871-32-7 2-(2-Phenylsulfanyl-phenyl)-6-morpholin-4-yl-pyran-4-one 

Relevant articles and documents

2,4,6-TRIS(DIALKYLAMINO)PYRYLIUM SALTS AND RELATED SYSTEMS, SYNTHESIS AND REACTION BEHAVIOUR

2,4,6-Tris(dialkylamino)pyrylium salts 9 and 2,6-bis(dialkylamino)-pyran-4-ones 11 as well as their thio-analogues 10, 12 have been prepared by a multi-step route starting with 1,1,5,5-tetrachloro-penta-1,4-dien-3-one(1).The tris(dialkylamino)-substituted 9, 10 undergo electrophilic substitution.They are better represented as polymethine-like systems.The 2,6-bis(dialkylamino)-substituted 11, 12 display a significantly increased donor-reactivity at the carbonyl-oxygen.

Pyranone, thiopyranone, and pyridone inhibitors of phosphatidylinositol 3-kinase related kinases. Structure-activity relationships for DNA-dependent protein kinase inhibition, and identification of the first potent and selective inhibitor of the ataxia telangiectasia mutated kinase

Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholinopyran-4-ones and 2-morpholino- thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6- (morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.

ATM inhibitors

The application concerns a compound of formula I: wherein one of P and Q is O, and the other of P and Q is CH, where there is a double bond between whichever of Q and P is CH and the carbon atom bearing the R3 group; Y is either O or S; R1