174784-50-0

Basic information

• Product Name: 1-(2-CHLORO-PHENYL)-3,4-DIHYDRO-ISOQUINOLINE
• Synonyms: 1-(2-CHLORO-PHENYL)-3,4-DIHYDRO-ISOQUINOLINE
• CAS NO: 174784-50-0
• Molecular Formula: C₁₅H₁₂ClN
• Molecular Weight: 241.72
• Mol File: 174784-50-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(2-CHLORO-PHENYL)-3,4-DIHYDRO-ISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-CHLORO-PHENYL)-3,4-DIHYDRO-ISOQUINOLINE(174784-50-0)
• EPA Substance Registry System: 1-(2-CHLORO-PHENYL)-3,4-DIHYDRO-ISOQUINOLINE(174784-50-0)

Safety Data

• Hazardous Substances Data: 174784-50-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-CHLORO-PHENYL)-3,4-DIHYDRO-ISOQUINOLINE is used as a pharmaceutical compound for its potential anticancer properties, given the known biological activities of isoquinoline derivatives. It may contribute to the development of treatments for various types of cancer.
1-(2-CHLORO-PHENYL)-3,4-DIHYDRO-ISOQUINOLINE is also used as an anti-inflammatory agent, leveraging the capacity of isoquinoline derivatives to modulate inflammatory responses and potentially alleviate symptoms associated with inflammatory conditions.
Furthermore, 1-(2-CHLORO-PHENYL)-3,4-DIHYDRO-ISOQUINOLINE is utilized for its antimicrobial properties, which can be harnessed in the development of new antibiotics or antimicrobial agents to combat resistant strains of bacteria and other pathogens.

Upstream product

• 609-65-4 o-chlorobenzoyl chloride 
• 64-04-0 phenethylamine 
• 304463-94-3 1-o-chlorophenyl-1,2,3,4-tetrahydroisoquinoline 
• 1190876-34-6 C₂₂H₂₀ClNO₂S 
• 118-91-2 ortho-chlorobenzoic acid 
• 38925-70-1 N-(2-phenylethyl)-o-chlorobenzamide 

Downstream Products

• 19007-59-1 2-(3,4-dihydro-isoquinolin-1-yl)-N-methyl-aniline 
• 304463-94-3 1-o-chlorophenyl-1,2,3,4-tetrahydroisoquinoline 
• 246851-84-3 (-)-1-(2-chlorophenyl)-1,2,3,4-tetrahydroisoquinoline 
• 174784-44-2 2-benzyl-1-(2-chlorophenyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline 
• 19209-04-2 1-(2-methylamino)-1,2,3,4-tetrahydroisoquinoline 
• 439614-58-1 1-(2-chlorophenyl)isoquinoline 

Relevant articles and documents

Substituent effects on axial chirality in 1-aryl-3,4-dihydroisoquinolines: controlling the rate of bond rotation

A series of 1-aryl-3,4-dihydroisoquinolines (DHIQs) were synthesized and their barriers to bond rotation were determined by means of VT-NMR, dynamic HPLC or racemization studies. Although they all presented lower rotational stability than the related 1-ar

Solvent-promoted highly selective dehydrogenation of tetrahydroisoquinolines without catalyst and hydrogen acceptor

An unusual solvent DMF-promoted dehydrogenation of 1-substituted 1,2,3,4-tetrahydroisoquinolines to synthesize cyclic imines is described. This environmentally friendly reaction features no requirement of any metal catalysts, oxidants, or hydrogen acceptors. A wide range of structurally varied 3,4-dihydroisoquinolines can be obtained with good yields and excellent chemoselectivities.

Enantioselective Synthesis of 1-Aryl-Substituted Tetrahydroisoquinolines Through Ru-Catalyzed Asymmetric Transfer Hydrogenation

A convenient and general asymmetric transfer hydrogenation of a wide array of 1-aryl-3,4-dihydroisoquinoline derivatives using a [RuIICl(η6-benzene)TsDPEN] complex in combination with a 5:2 HCOOH-Et3N azeotropic mixture as a hydrogen source was developed. Under mild reaction conditions, the described catalytic transformation secured a practical synthetic access to the corresponding valuable chiral 1-aryltetrahydroisoquinoline units with high atom economy, a broad substrate scope, high isolated yields (up to 97%) and good to excellent enantioselectivities (up to 99% ee). It was found that the stereochemical outcome of the reaction was strongly influenced by both the structure of the catalyst and the substituents present on the substrate. The synthetic utility of the present protocol has been demonstrated through the asymmetric synthesis of several biologically important alkaloids including the antiepileptic drug agent 1c, as well as (-)-nor-cryptostyline alkaloids I and II.

Mild and efficient syntheses of 1-aryl-3,4-dihydroisoquinolines and 1-aryl-3,4-dihydro-β-carbolines via regiospecific β-eliminations of the corresponding N-tosyl-1,2,3,4-tetrahydroisoquinolines and N-tosyl-1,2,3,4-tetrahydro-β-carbolines

(Chemical Equation Presented) Treatment of N-tosyl-1-aryl-1,2,3,4- tetrahydro-isoquinolines or N-tosyl-1-aryl-1, 2,3,4-tetrahydro-β-carbolines with a strong base such as NaOH or KOH at 70 °C in dimethylsulfoxide (DMSO) produced 1-aryl-3,4-dihydroisoquinolines or 1-aryl-3,4-dihydro-β- carbolines in good yields via mild and regiospecific β-eliminations. A dramatic solvent effect was observed, DMSO was crucial for the reactions. The temperature is also crucial for the reactions and should be kept between 60 and 80 °C. Copyright Taylor & Francis Group, LLC.

Design, synthesis, and inhibition of platelet aggregation for some 1-o-chlorophenyl-1,2,3,4-tetrahydroisoquinoline derivatives

Four analogs proved to be potential antiplatelet aggregation agents, and compound 9 (TQP-3, applying for patent), which inhibits ADP-induced human platelet aggregation with IC50 values of approximately 0.206 nM was the most active. Based on ticlopidine active as an ADP receptor antagonist for inhibiting platelet aggregation in clinical test, and upon finding (±)-1,2-substituted-7-sulfonylamide/amide-1,2,3,4-tetrahydroisoquinoline (11-31) inhibited of platelet aggregation, a series of (±)-1-o- chlorophenyl-2-substituted-tetrahydroisoquinoline derivatives was designed and synthesized. Four analogs proved to be potential antiplatelet aggregation agents, and compound 9 (TQP-3, applying for patent) which inhibits ADP-induced human platelet aggregation with IC50 values of approximately 0.206 nM was the most active. Compound 2 is more active than compound 1, which (Type I) is similar to ticlopidine. This is because there is a spacial hindrance in compound 1, and the o-chloro group of compound 2 may play the same a role as o-chloro group of ticlopidine. On the other hand, with the different substitutions at different positions on the 2-substituted phenylacyl group, their inhibition of platelet aggregation differs. These compounds with m-substituted group (5, 7, 9) showed a higher IC50 value for inhibiting ADP-induced human platelet aggregation than those with o-substituted group (4, 6) or p-substituted group (3, 8). It was observed that their inhibition is bromine-substituted derivative (9), chlorine-substituted derivative (7), and nitro-substituted derivative (5) in turn. Moreover, these compounds (Type II) may be more similar to clopidogrel than to ticlopidine due to the acyl group at 2 position of the nucleus playing a role as the ester group of clopidogrel. It was conjectured that these analogs function as a potential antiplatelet aggregation role by acting as ADP receptor antagonists.

Synthetic approaches to 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid

In connection with our research of new antitumor compounds, previously undescribed approaches to the 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid 9 are reported here. Two related accesses from phenylethylamine or amphetamine were investigated and were found to be successful. A more robust synthesis, using Suzuki's cross-coupling between 2-chlorophenylboronic acid 15 and the previously unreported methyl-1-bromoisoquinoline-3-carboxylate 14 was also developed. This synthetic route provides the ground for a combinatorial approach to the core structure of new potential peripheral benzodiazepine receptor ligands.

Synthesis of racemic 1,2,3,4-tetrahydroisoquinolines and their resolution

1-Aniline-substituted 3,4-dihydroisoquinolines were obtained in various ways using the Bischler-Napieralski reaction. The effect of the protecting group at the aniline nitrogen atom on the course of the reaction has been studied and it was found that the N-phthalyl group was stable under the cyclization conditions. The dihydroisoquinolines were reduced to the racemic 1,2,3,4-tetrahydroisoquinolines which were resolved by crystallization of the diastereomeric tartrates. Two examples of 1,2,3, 4-tetrahydroisoquinolines were obtained in optically pure form (>99% ee).