69381-55-1

Basic information

• Product Name: 8-phenyl-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 8-phenyl-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 69381-55-1
• Molecular Weight: 209.291
• Mol File: 69381-55-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 8-phenyl-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 8-phenyl-1,2,3,4-tetrahydroisoquinoline(69381-55-1)
• EPA Substance Registry System: 8-phenyl-1,2,3,4-tetrahydroisoquinoline(69381-55-1)

Safety Data

• Hazardous Substances Data: 69381-55-1(Hazardous Substances Data)

Upstream product

• 34784-07-1 8-chloroisoquinoline 
• 98-80-6 phenylboronic acid 
• 119-65-3 isoquinoline 
• 92426-42-1 5-chloro-8-phenylisoquinoline 
• 927801-25-0 8-bromo-5-chloroisoquinoline 
• 5430-45-5 5-chloro-isoquinoline 

Relevant articles and documents

Synthesis and biochemical evaluation of lid-open D-amino acid oxidase inhibitors

Most of the known inhibitors of D-amino acid oxidase (DAAO) are small polar molecules recognized by the active site of the enzyme. More recently a new class of DAAO inhibitors has been disclosed that interacts with loop 218?224 at the top of the binding pocket. These compounds have a significantly larger size and more beneficial physicochemical properties than most reported DAAO inhibitors, however, their structure-activity relationship is poorly explored. Here we report the synthesis and evaluation of this type of DAAO inhibitors that open the lid over the active site of DAAO. In order to collect relevant SAR data we varied two distinct parts of the inhibitors. A systematic variation of the pendant aromatic substituents according to the Topliss scheme resulted in DAAO inhibitors with low nanomolar activity. The activity showed low sensitivity to the substituents investigated. The variation of the linker connecting the pendant aromatic moiety and the acidic headgroup revealed that the interactions of the linker with the enzyme were crucial for achieving significant inhibitory activity. Structures and activities were analyzed based on available X-ray structures of the complexes. Our findings might support the design of drug-like DAAO inhibitors with advantageous physicochemical properties and ADME profile.

Versatile and Efficient Synthesis of Aryl-1,2,3,4-tetrahydroisoquinolines: Nickel(II) Phosphine Ligand Catalyzed Coupling of Arylmagnesium Halides to Haloisoquinolines

Dichloronickel(II) (dppp) was used as catalyst to prepare some previously unreported arylisoquinolines 3, which were in turn hydrogenated to aryl-1,2,3,4-tetrahydroisoquinolines 2.This procedure is the most direct and ef