912824-70-5

Basic information

• Product Name: 5-[2-bromoanilino(methylthio)methylene]-2,2-dimethyl[1,3]dioxane-4,6-dione
• Synonyms: 5-[2-bromoanilino(methylthio)methylene]-2,2-dimethyl[1,3]dioxane-4,6-dione
• CAS NO: 912824-70-5
• Molecular Weight: 372.239
• Mol File: 912824-70-5.mol

Chemical Properties

• CAS DataBase Reference: 5-[2-bromoanilino(methylthio)methylene]-2,2-dimethyl[1,3]dioxane-4,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[2-bromoanilino(methylthio)methylene]-2,2-dimethyl[1,3]dioxane-4,6-dione(912824-70-5)
• EPA Substance Registry System: 5-[2-bromoanilino(methylthio)methylene]-2,2-dimethyl[1,3]dioxane-4,6-dione(912824-70-5)

Safety Data

• Hazardous Substances Data: 912824-70-5(Hazardous Substances Data)

Upstream product

• 100981-05-3 5-[bis(methylthio)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 615-36-1 2-bromoaniline 

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.

DNA-PK INHIBITORS

Compounds of formula: (I) wherein A, B and D are respectively selected from the group consisting of: (i) CH, NH, C; (ii) CH, N, N; and (iii) CH, O, C; the dotted lines represent two double bonds in the appropriate locations; and where Z is selected from S, O, C(=O), CH2 and NH are disclosed for use in inhibiting DNA-PK.