59224-74-7

Basic information

• Product Name: 1-(4'-METHOXY)PHENYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
• Synonyms: 1-(4'-METHOXY)PHENYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
• CAS NO: 59224-74-7
• Molecular Formula: C₁₆H₁₇NO
• Molecular Weight: 239.31
• Product Categories: Tetrahydroisoquinolines
• Mol File: 59224-74-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 84-85 °C(Solv: cyclohexane (110-82-7))
• Boiling Point: 376.4±30.0 °C(Predicted)
• Appearance: /
• Density: 1.085±0.06 g/cm3(Predicted)
• PKA: 8.97±0.40(Predicted)
• CAS DataBase Reference: 1-(4'-METHOXY)PHENYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4'-METHOXY)PHENYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(59224-74-7)
• EPA Substance Registry System: 1-(4'-METHOXY)PHENYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(59224-74-7)

Safety Data

• Hazardous Substances Data: 59224-74-7(Hazardous Substances Data)

Usage

Description

1-(4'-METHOXY)PHENYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE is a complex chemical compound characterized by its unique molecular structure, which includes a phenyl ring with a methoxy group and a tetrahydro-isoquinoline ring. 1-(4'-METHOXY)PHENYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE holds potential pharmaceutical applications due to its resemblance to isoquinoline alkaloids, which are known for their diverse biological activities such as anti-inflammatory, anticancer, and antioxidant properties. Further research is essential to comprehend the full pharmacological profile of 1-(4'-METHOXY)PHENYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE and its potential advantages for human health.

Uses

Used in Pharmaceutical Industry:
1-(4'-METHOXY)PHENYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE is used as a potential pharmaceutical agent for its structural similarity to isoquinoline alkaloids, which exhibit various biological activities. 1-(4'-METHOXY)PHENYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE may be utilized in the development of new drugs targeting anti-inflammatory, anticancer, and antioxidant applications due to its potential to interact with biological systems in a similar manner to known isoquinoline alkaloids.
Used in Research and Development:
In the field of scientific research, 1-(4'-METHOXY)PHENYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE serves as a valuable compound for studying the structure-activity relationships of isoquinoline alkaloids. Its use in research can facilitate the discovery of novel therapeutic agents with improved efficacy and reduced side effects, contributing to advancements in medicine and healthcare.

Upstream product

• 59224-73-6 1-(4'-methoxylphenyl)-3,4-dihydroisoquinoline 
• 123-11-5 4-methoxy-benzaldehyde 
• 64-04-0 phenethylamine 
• 6346-07-2 4-methoxy-N-(2-phenylethyl)benzamide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 139437-83-5 ethyl 1-(4-methoxyphenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 100-09-4 4-methoxybenzoic acid 

Downstream Products

• 1620820-59-8 1-(4-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Discovery of quinuclidine modulators of cellular progranulin

Phenotypic screening of an annotated small molecule library identified the quinuclidine tetrahydroisoquinoline solifenacin (1) as a robust enhancer of progranulin secretion with single digit micromolar potency in a murine microglial (BV-2) cell line. Subsequent SAR development led to the identification of 29 with a 38-fold decrease in muscarinic receptor antagonist activity and a 10-fold improvement in BV-2 potency.

Design, Synthesis, and Biological Evaluation of Tetrahydroisoquinoline-Based Histone Deacetylase 8 Selective Inhibitors

Histone deacetylase 8 (HDAC8) is a promising drug target for multiple therapeutic applications. Here, we describe the modeling, design, synthesis, and biological evaluation of a novel series of C1-substituted tetrahydroisoquinoline (TIQ)-based HDAC8 inhibitors. Minimization of entropic loss upon ligand binding and use of the unique HDAC8 "open" conformation of the binding site yielded a successful strategy for improvement of both HDAC8 potency and selectivity. The TIQ-based 3g and 3n exhibited the highest 82 and 55 nM HDAC8 potency and 330- and 135-fold selectivity over HDAC1, respectively. Selectivity over other class I isoforms was comparable or better, whereas inhibition of HDAC6, a class II HDAC isoform, was below 50% at 10 μM. The cytotoxicity of 3g and 3n was evaluated in neuroblastoma cell lines, and 3n displayed concentration-dependent cytotoxicity similar to or better than that of PCI-34051. The selectivity of 3g and 3n was confirmed in SH-SY5Y cells as both did not increase the acetylation of histone H3 and α-tubulin. Discovery of the novel TIQ chemotype paves the way for the development of HDAC8 selective inhibitors for therapeutic applications.

One-step preparation of 1-substituted tetrahydroisoquinolines via the Pictet-Spengler reaction using zeolite catalysts

A new, one-step variation of the Pictet-Spengler reaction has been elaborated using a small pore size zeolite as the catalyst. A new, environmentally friendly variation of the Pictet-Spengler reaction has been elaborated using a small pore size zeolite. The easily separable and recyclable catalyst provided high conversions and a shorter reaction time than the classical acetic acid or trifluoroacetic acid.