92905-81-2

Basic information

• Product Name: 3-phenyl-2H-2,7-naphthyridin-1-one
• CAS NO: 92905-81-2
• Molecular Formula: C₁₄H₁₀N₂O
• Molecular Weight: 222.246
• Mol File: 92905-81-2.mol

Chemical Properties

• Boiling Point: 499.6°Cat760mmHg
• Flash Point: 255.9°C
• Density: 1.252g/cm³
• CAS DataBase Reference: 3-phenyl-2H-2,7-naphthyridin-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-2H-2,7-naphthyridin-1-one(92905-81-2)
• EPA Substance Registry System: 3-phenyl-2H-2,7-naphthyridin-1-one(92905-81-2)

Safety Data

• Hazardous Substances Data: 92905-81-2(Hazardous Substances Data)

Upstream product

• 112349-20-9 1-(2,6-dichloro-benzyl)-4-phenacylidene-1,4-dihydro-pyridine-3-carboxylic acid amide 
• 1449753-36-9 7-benzyl-3-phenyl-2,7-naphthyridin-1(7H)-one 
• 98-92-0 nicotinamide 
• 5096-13-9 1-benzylnicotinamide chloride 
• 118159-97-0 4-(phenylethynyl)pyridine-3-carbonitrile 
• 154237-70-4 4-bromopyridine-3-carbonitrile 
• 536-74-3 phenylacetylene 
• 5657-55-6 3-phenyl-1H-pyrano(3,4-c)pyridin-1-one 

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.

TANKYRASE INHIBITORS

The present invention relates to a compound of formula I wherein X is C(R6) or N, Y is C or N, and ring A, ring B, R1 and R2 have the meanings defined herein, provided that when ring B is carbocyclic, X is C(R6); or a pharmaceutically acceptable salt or solvate thereof. The compounds are tankyrase-1 and tankyrase-2 inhibitors and are useful in the treatment of a number of conditions, including cancer.

Tandem synthesis of substituted 2,7-naphthyridin-1(7H)-ones via Reissert reaction/intramolecular nucleophilic addition/oxidation dehydrogenation

A convenient method for the synthesis of substituted 2,7-naphthyridin-1(7H) -ones has been developed. This method was carried out starting from a simple nicotinamide salts via a tandem process including Reissert reaction, intramolecular nucleophilic addition and oxidation dehydrogenation. Using this method, a variety of substituted 2,7-naphthyridin-1(7H)-ones were obtained in good yields.