89242-09-1

Basic information

• Product Name: 3-Isoquinolinecarboxylicacid, 1-(2-chlorophenyl)-
• Synonyms: 1-(2-Chlorophenyl)isoquinoline-3-carboxylicacid; PK 11209
• CAS NO: 89242-09-1
• Molecular Formula: C16H10 Cl N O2
• Molecular Weight: 283.714
• Mol File: 89242-09-1.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 3-Isoquinolinecarboxylicacid, 1-(2-chlorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Isoquinolinecarboxylicacid, 1-(2-chlorophenyl)-(89242-09-1)
• EPA Substance Registry System: 3-Isoquinolinecarboxylicacid, 1-(2-chlorophenyl)-(89242-09-1)

Safety Data

• Hazardous Substances Data: 89242-09-1(Hazardous Substances Data)

Usage

Family

Isoquinoline

Structural feature

Derivative of isoquinolinecarboxylic acid

Substituent

2-chlorophenyl group attached to the 1-position

Applications

Building block in synthesis of pharmaceuticals and agrochemicals
Versatile reactivity
Functional group compatibility

Biological activities

Studied for potential pharmacological properties
Target for drug discovery and development

Overall significance

Valuable chemical intermediate
Diverse applications in medicinal chemistry and drug synthesis

Upstream product

• 53631-70-2 d,l-norephedrine hydrochloride 
• 419535-34-5 2-chloro-N-(2-hydroxy-1-methyl-2-phenylethyl)benzamide 
• 63586-82-3 1-Oxo-1,2,3,4-tetrahydro-3(R,S)-isoquinolinecarboxylic Acid 
• 23364-15-0 (DL)-methyl 1-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 60-15-1 2-amino-1-phenylpropane 
• 76005-94-2 2-chlorophenyl(phenyl)methanimine 
• 85532-75-8 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide 
• 40547-06-6 4-benzylidene-2-(2-chloro-phenyl)-4H-oxazol-5-one 
• 501084-68-0 1-(2-chloro-phenyl)-3-dibromomethyl-isoquinoline 
• 439614-64-9 1-(2-chlorophenyl)-3-methylisoquinoline N-oxide 
• 439614-62-7 1-bromoisoquinoline-3-carboxylic acid methyl ester 
• 609-65-4 o-chlorobenzoyl chloride 
• 93010-73-2 N-(β-phenyl)isopropyl-o-chlorobenzamide 
• 69454-42-8 1-hydroxyisoquinoline-3-carboxylic acid methyl ester 

Downstream Products

• 1009737-69-2 C₃₄H₂₄Cl₂N₄O₂ 
• 1456688-36-0 PK 
• 1456688-40-6 PK 
• 85532-75-8 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide 
• 110012-96-9 (S)-(+)-1-(2-chlorophenyl)-N-(1-methylpropyl)-N-<2-(carbobenzoxyamino)ethyl>-3-isoquinolinecarboxamide 
• 110012-95-8 (R)-(-)-1-(2-chlorophenyl)-N-(1-methylpropyl)-N-<2-(carbobenzoxyamino)ethyl>-3-isoquinolinecarboxamide 
• 109960-10-3 (+/-)-1-(2-chlorophenyl)-N-(1-methylpropyl)-N-<2-(carbobenzoxyamino)ethyl>-3-isoquinolinecarboxamide 
• 110012-99-2 (S)-1-(2-chlorophenyl)-N-(1-methylpropyl)-N-(2-aminoethyl)-3-isoquinolinecarboxamide 
• 110012-97-0 (R)-(-)-1-(2-chlorophenyl)-N-(1-methylpropyl)-N-(2-aminoethyl)-3-isoquinolinecarboxamide 
• 109960-11-4 (+/-)-1-(2-chlorophenyl)-N-(1-methylpropyl)-N-(2-aminoethyl)-3-isoquinolinecarboxamide 

Relevant articles and documents

Redox-Neutral Manganese(I)-Catalyzed C?H Activation: Traceless Directing Group Enabled Regioselective Annulation

A strategy is reported in which traceless directing groups (TDGs) are used to promote the redox-neutral MnI-catalyzed regioselective synthesis of N-heterocycles. Alkyne coupling partners bearing a traceless directing group, which serves as both the chelator and internal oxidant, were used to control the regioselectivity of the annulation reactions. This operationally simple approach is highly effective with previously challenging unsymmetrical alkyne systems, including unbiased dialkyl alkynes, with perfect regioselectivity. The simple conditions and the ability to carry out synthesis on a gram scale underscore the usefulness of this method. The application of this strategy in the concise synthesis of the bioactive compound PK11209 and the pharmaceutical moxaverine is also described.

HETEROCYCLIC DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND METHODS OF USE THEREOF

The present invention relates to novel quinoxaline, quinazoline and phthalazine derivatives as well as multimeric derivatives, methods for their preparation, pharmaceutical compositions including such compounds, and methods of using these compounds for the treatment and prevention of brain damage resulting from brain injury, especially secondary brain damage due to traumatic brain injury (TBI). The compounds of the invention are also useful in treating and preventing neurodegenerative diseases.

Optimized palladium-based approaches to analogues of PK 11195

(Chemical Equation Presented) The peripheral-type benzodiazepine receptor ligands such as PK 11195 and Ro 5-4864 were found more than twenty years ago in the course of research on neurobiology. These ligands were instrumental in pointing out an involvement of the peripheral-type benzodiazepine receptor (PBR) in apoptosis processes. With in mind an improvement of the solubility of PK 11195 in biological media, we report here improved reaction conditions for the palladium-based arylation reaction of alkyl 1-bromoisoquinoline-3-carboxylates and its ethyl 4-bromoquinoline-2-carboxylate isomer. The use of [1,1′-bis(diphenylphosphino) ferrocene] dichloropalladium as a precatalyst enabled a much improved preparation of an array of the 1-arylisoquinoline-3- carboxylates as well as 4-arylquinoline-3-carboxylates. This work should pave the way for the design of chemical probes aiming at the elucidation of the PBR biological role(s).