1450605-85-2

Basic information

• Product Name: 5-amino-3-(4-trifluoromethylphenyl)isoquinolin-1-one
• Synonyms: 5-amino-3-(4-trifluoromethylphenyl)isoquinolin-1-one
• CAS NO: 1450605-85-2
• Molecular Weight: 304.271
• Mol File: 1450605-85-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-amino-3-(4-trifluoromethylphenyl)isoquinolin-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-3-(4-trifluoromethylphenyl)isoquinolin-1-one(1450605-85-2)
• EPA Substance Registry System: 5-amino-3-(4-trifluoromethylphenyl)isoquinolin-1-one(1450605-85-2)

Safety Data

• Hazardous Substances Data: 1450605-85-2(Hazardous Substances Data)

Upstream product

• 573-54-6 2-bromo-3-nitro-benzoic acid 
• 1450605-75-0 5-nitro-3-(4-trifluoromethylphenyl)isoquinolin-1(2H)-one 
• 258346-69-9 1-(4-trifluoromethyl-phenyl)-butane-1,3-dione 

Relevant articles and documents

One-pot tandem Hurtley-retro-Claisen-cyclisation reactions in the synthesis of 3-substituted analogues of 5-aminoisoquinolin-1-one (5-AIQ), a water-soluble inhibitor of PARPs

Poly(ADP-ribose)polymerase-1 (PARP-1) is an important target for drug design for several therapeutic applications. 5-Aminoisoquinolin-1-one (5-AIQ) is a highly water-soluble lead compound; synthetic routes to 3-substituted analogues were explored. Tandem Hurtley coupling of β-diketones with 2-bromo-3-nitrobenzoic acid, retro-Claisen acyl cleavage and cyclisation gave the corresponding 3-substituted 5-nitroisocoumarins. Treatment with ammonia at high temperature and reduction with tin(II) chloride gave eleven target 3-substituted 5-AIQs, which were all soluble in water (>1% w/v) as their HCl salts. Most were more potent than 5-AIQ as inhibitors of PARP-1 and of PARP-2 in vitro, the most active being 5-amino-3-methylisoquinolin-1-one (PARP-1: IC 50 = 0.23 μM vs IC50 = 1.6 μM for 5-AIQ). Some rationalisation of the SAR was achieved through molecular modelling.