53987-60-3

Basic information

• Product Name: Isoquinoline,1,3-dibromo-
• Synonyms: 1,3-dibromo-isoquinoline;1,3-Dibromisochinolin;isoquinoline,1,3-dibromo
• CAS NO: 53987-60-3
• Molecular Formula: C₉H₅Br₂N
• Molecular Weight: 286.95
• Mol File: 53987-60-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 370.9 °C at 760 mmHg
• Flash Point: 178.1 °C
• Appearance: /
• Density: 1.923 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.49±0.50(Predicted)
• CAS DataBase Reference: Isoquinoline,1,3-dibromo-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoquinoline,1,3-dibromo-(53987-60-3)
• EPA Substance Registry System: Isoquinoline,1,3-dibromo-(53987-60-3)

Safety Data

• Hazardous Substances Data: 53987-60-3(Hazardous Substances Data)

Usage

General Description

Isoquinoline, 1,3-dibromo- is a chemical compound with the molecular formula C9H6Br2N. It is a derivative of isoquinoline, which is a nitrogen-containing organic compound commonly found in plants and animals. The 1,3-dibromo- substitution indicates that two bromine atoms are attached at the 1 and 3 positions on the isoquinoline ring. Isoquinoline,1,3-dibromo- is primarily used in organic synthesis and medicinal chemistry as a building block to create more complex organic molecules. It may also have potential applications in the field of pharmaceuticals and agrochemicals due to its unique structural properties. Additionally, it is important to handle this chemical with caution as it may pose potential health and environmental risks.

Upstream product

• 102879-33-4 5,6,7,8-tetrahydroisoquinolin-3-ol 
• 89-51-0 Homophthalic acid 
• 4456-77-3 4H-isoquinolin-1,3-dione 

Downstream Products

• 34784-02-6 3-bromoisoquinoline 
• 1613435-47-4 1-methoxy-5-nitro-3-(2-trifluoromethylphenyl)isoquinoline 
• 1613435-50-9 1-methoxy-5-nitro-3-(2-phenylethynyl)isoquinoline 
• 1613435-48-5 1-methoxy-5-nitro-3-(3-trifluoromethylphenyl)isoquinoline 
• 1613435-44-1 1-methoxy-5-nitro-3-(4-trifluoromethylphenyl)isoquinoline 
• 1613435-43-0 3-(4-fluorophenyl)-1-methoxy-5-nitroisoquinoline 
• 1613435-40-7 3-(2-chlorophenyl)-1-methoxy-5-nitroisoquinoline 
• 1613435-41-8 3-(3-chlorophenyl)-1-methoxy-5-nitroisoquinoline 
• 1613435-42-9 3-(2,6-dichlorophenyl)-1-methoxy-5-nitroisoquinoline 
• 1613435-45-2 3-(3-cyanophenyl)-1-methoxy-5-nitroisoquinoline 
• 1613435-46-3 3-(4-cyanophenyl)-1-methoxy-5-nitroisoquinoline 
• 1613435-30-5 5-amino-1-methoxy-3-(2-trifluoromethylphenyl)isoquinoline 
• 1613435-32-7 5-amino-1-methoxy-3-(3-trifluoromethylphenyl)isoquinoline 
• 1613435-24-7 5-amino-1-methoxy-3-(4-trifluoromethylphenyl)isoquinoline 

Relevant articles and documents

Exploration of the nicotinamide-binding site of the tankyrases, identifying 3-arylisoquinolin-1-ones as potent and selective inhibitors in vitro

Tankyrases-1 and -2 (TNKS-1 and TNKS-2) have three cellular roles which make them important targets in cancer. Using NAD+ as a substrate, they poly(ADP-ribosyl)ate TRF1 (regulating lengths of telomeres), NuMA (facilitating mitosis) and axin (in wnt/β-catenin signalling). Using molecular modelling and the structure of the weak inhibitor 5-aminoiso quinolin-1-one, 3-aryl-5-substituted-isoquinolin-1-ones were designed as inhibitors to explore the structure-activity relationships (SARs) for binding and to define the shape of a hydrophobic cavity in the active site. 5-Amino-3-arylisoquinolinones were synthesised by Suzuki-Miyaura coupling of arylboronic acids to 3-bromo-1-methoxy-5-nitro-isoquinoline, reduction and O-demethylation. 3-Aryl-5-methylisoquinolin-1-ones, 3-aryl-5-fluoroisoquinolin-1-ones and 3-aryl-5-methoxyisoquinolin-1-ones were accessed by deprotonation of 3-substituted-N,N,2-trimethylbenzamides and quench with an appropriate benzonitrile. SAR around the isoquinolinone core showed that aryl was required at the 3-position, optimally with a para-substituent. Small meta-substituents were tolerated but groups in the ortho-positions reduced or abolished activity. This was not due to lack of coplanarity of the rings, as shown by the potency of 4,5-dimethyl-3-phenylisoquinolin-1-one. Methyl and methoxy were optimal at the 5-position. SAR was rationalised by modelling and by crystal structures of examples with TNKS-2. The 3-aryl unit was located in a large hydrophobic cavity and the para-substituents projected into a tunnel leading to the exterior. Potency against TNKS-1 paralleled potency against TNKS-2. Most inhibitors were highly selective for TNKSs over PARP-1 and PARP-2. A range of highly potent and selective inhibitors is now available for cellular studies.