59224-74-7

Usage

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 academic research and scientific papers

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.

PROGRANULIN MODULATORS AND METHODS OF USING THE SAME

Provided herein are compounds that modulate progranulin and methods of using the compounds in progranulin-associated disorders, such as Frontotemperal dementia (FTD).

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.

TRP-M8 RECEPTOR LIGANDS AND THEIR USE IN TREATMENTS

Tetrahydroisoquinoline compounds of formula (I), and compositions containing them, for the treatment of acute, inflammatory and neurophatic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neurophatic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintened pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritus, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

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.

Phencyclidine-like Effects of Tetrahydroisoquinolines and Related Compounds

A series of 1,2,3,4-tetrahydroisoquinolines, tetrahydrothienopyridines, and related compounds were evaluated for their ability to inhibit binding of -1--N-allylnormetazocine to phencyclidine (PCP) and ? receptors, respectively.A representative series of compounds was evaluated in behavioral assays to determine the ability of the compounds to induce PCP-like stereotyped behavior and ataxia.All of the compounds caused stereotyped behavior and ataxia, indicating their agonist actions at the PCP site.