1613435-79-2

Basic information

• Product Name: 7-(4-chlorophenyl)-1-methyl-5-oxo-1,6-naphthyridin-1-ium iodide
• Synonyms: 7-(4-chlorophenyl)-1-methyl-5-oxo-1,6-naphthyridin-1-ium iodide
• CAS NO: 1613435-79-2
• Molecular Weight: 398.631
• Mol File: 1613435-79-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 7-(4-chlorophenyl)-1-methyl-5-oxo-1,6-naphthyridin-1-ium iodide(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(4-chlorophenyl)-1-methyl-5-oxo-1,6-naphthyridin-1-ium iodide(1613435-79-2)
• EPA Substance Registry System: 7-(4-chlorophenyl)-1-methyl-5-oxo-1,6-naphthyridin-1-ium iodide(1613435-79-2)

Safety Data

• Hazardous Substances Data: 1613435-79-2(Hazardous Substances Data)

Upstream product

• 1126-46-1 Methyl 4-chlorobenzoate 
• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 20577-27-9 pyrid-2-one-3-carbonitrile 
• 637-87-6 1-Chloro-4-iodobenzene 
• 78704-49-1 1-(4-chlorophenyl)-2-trimethylsilylacetylene 
• 18362-49-7 1,3-bis(4-chlorophenyl)propane-1,3-dione 
• 1613436-07-9 7-(4-chlorophenyl)pyrano[4,3-b]pyridin-5-one 
• 35905-85-2 2-bromonicotinic acid 
• 511240-96-3 7-(4-chlorophenyl)-1,6-naphthyridin-5-one 
• 74-88-4 methyl iodide 
• 873-73-4 4-n-chlorophenylacetylene 
• 1613435-68-9 2-(4-chlorophenylethynyl)-3-cyanopyridine 
• 20577-26-8 2-bromonicotinonitrile 

Relevant articles and documents

Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases

Abstract The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl)ate their target proteins using NAD+ as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with β-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused >1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2.