166398-33-0

Usage

Uses

Used in Pharmaceutical Synthesis:
Tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate is utilized as a key intermediate in the development of new pharmaceuticals, leveraging its structural features to create molecules with potential therapeutic effects. Its ability to form coordination complexes with metal ions also aids in the design of drugs with enhanced pharmacological properties.
Used in Agrochemical Development:
In the agrochemical industry, tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate is employed as a precursor in the synthesis of novel compounds with pesticidal or herbicidal activities. Its unique chemical properties allow for the creation of agrochemicals that can address specific challenges in crop protection.
Used in Material Science:
tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate finds application in material science as a component in the synthesis of advanced materials with tailored properties. Its versatility in forming coordination complexes makes it suitable for the development of materials with applications in catalysis, sensors, and other high-tech fields.
Used in Organic Synthesis as a Building Block:
Tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate is used as a building block in organic synthesis for the creation of a wide range of organic compounds. Its structural elements, including the cyano and dihydroisoquinoline groups, provide opportunities for further functionalization and the synthesis of complex organic molecules.
Used in Catalysis as a Ligand:
In the field of catalysis, tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate is used as a versatile ligand to form coordination complexes with metal ions. This application is crucial for enhancing the efficiency and selectivity of various catalytic processes, contributing to advancements in chemical reactions and industrial processes.

InChI:InChI=1/C15H18N2O2/c1-15(2,3)19-14(18)17-7-6-12-8-11(9-16)4-5-13(12)10-17/h4-5,8H,6-7,10H2,1-3H3

Upstream product

• 557-21-1 zinc(II) cyanide 
• 158984-84-0 6-trifluoromethanesulfonyloxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 166398-34-1 1,2,3,4-tetrahydroisoquinoline-6-carbonitrile 
• 893566-74-0 6-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline 
• 226942-29-6 6-bromo-1,2,3,4-tetrahydroisoquinoline 
• 158984-83-9 N-tert-butoxycarbonyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline 
• 59839-23-5 6-hydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide 
• 557-21-1 dicyanozinc 

Downstream Products

• 1286751-23-2 tert-butyl 6-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1286751-25-4 2-isopropoxy-5-(3-(1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)benzonitrile trifluoroacetate 
• 1286751-29-8 ethyl 3-(6-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydroisoquinolin-2(1H)-yl)propanoate 
• 1286750-76-2 sodium 3-(6-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydroisoquinolin-2(1H)-yl)propanoate 
• 1333995-67-7 5-(3-(2-(1,3-dihydroxypropan-2-yl)-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile 
• 1333996-68-1 5-(3-(2-(1,3-dihydroxypropan-2-yl)-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile hydrochloride 
• 1333996-67-0 5-(3-(2-(2,2-dimethyl-1,3-dioxan-5-yl)-1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile 
• 166398-34-1 1,2,3,4-tetrahydroisoquinoline-6-carbonitrile 

Relevant academic research and scientific papers

Ligand-based rational design, synthesis and evaluation of novel potential chemical chaperones for opsin

Inherited blinding diseases retinitis pigmentosa (RP) and a subset of Leber's congenital amaurosis (LCA) are caused by the misfolding and mistrafficking of rhodopsin molecules, which aggregate and accumulate in the endoplasmic reticulum (ER), leading to photoreceptor cell death. One potential therapeutic strategy to prevent the loss of photoreceptors in these conditions is to identify opsin-binding compounds that act as chemical chaperones for opsin, aiding its proper folding and trafficking to the outer cell membrane. Aiming to identify novel compounds with such effect, a rational ligand-based approach was applied to the structure of the visual pigment chromophore, 11-cis-retinal, and its locked analogue 11-cis-6mr-retinal. Following molecular docking studies on the main chromophore binding site of rhodopsin, 49 novel compounds were synthesized according to optimized one-to seven-step synthetic routes. These agents were evaluated for their ability to compete for the chromophore binding site of opsin, and their capacity to increase the trafficking of the P23H opsin mutant from the ER to the cell membrane. Different new molecules displayed an effect in at least one assay, acting either as chemical chaperones or as stabilizers of the 9-cis-retinal-rhodopsin complex. These compounds could provide the basis to develop novel therapeutics for RP and LCA.

1-(2-hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile derivatives as potent and tissue selective androgen receptor modulators

We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.

Discovery of a selective S1P1 receptor agonist efficacious at low oral dose and devoid of effects on heart rate

Gilenya (fingolimod, FTY720) was recently approved by the U.S. FDA for the treatment of patients with remitting relapsing multiple sclerosis (RRMS). It is a potent agonist of four of the five sphingosine 1-phosphate (S1P) G-protein-coupled receptors (S1P1 and S1P3-5). It has been postulated that fingolimod's efficacy is due to S1P1 agonism, while its cardiovascular side effects (transient bradycardia and hypertension) are due to S1P3 agonism. We have discovered a series of selective S1P 1 agonists, which includes 3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy] phenyl}-1,2,4-oxadiazol-3-yl)-5-methyl-3,4-dihydro-2(1H)-isoquinolinyl] propanoate, 20, a potent, S1P3-sparing, orally active S1P1 agonist. Compound 20 is as efficacious as fingolimod in a collagen-induced arthritis model and shows excellent pharmacokinetic properties preclinically. Importantly, the selectivity of 20 against S1P3 is responsible for an absence of cardiovascular signal in telemetered rats, even at high dose levels.

Discovery of a brain-penetrant S1P3-sparing direct agonist of the S1P1 and S1P5 receptors efficacious at low oral dose

2-Amino-2-(4-octylphenethyl)propane-1,3-diol 1 (fingolimod, FTY720) has been recently marketed in the United States for the treatment of patients with remitting relapsing multiple sclerosis (RRMS). Its efficacy has been primarily linked to the agonism on

MODULATORS OF TOLL-LIKE RECEPTORS

Provided are modulators of TLRs of Formula II: pharmaceutically acceptable salts thereof, compositions containing such compounds, and therapeutic methods that include the administration of such compounds.

Expeditious one-pot, four-step preparation of 2-t-butoxycarbonyl-6-hydroxy- 1,2,3,4-tetrahydroisoquinoline and an improved conversion to its 6-cyano derivative

3-Methoxy-phenethylamine was subjected to a sequential imination/Pictet- Spengler/demethylation/Boc protection sequence that allowed a one-pot preparation of N-Boc-6-hydroxy-1,2,3,4-tetrahydroisoquinoline 1. This intermediate was elaborated almost quantit

S1P1 AGONISTS COMPRISING A BICYCLIC N-CONTAINING RING

The present invention relates to novel compounds of formula (I) having S1P1 agonist activity, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders.

COMPOUND HAVING S1P RECEPTOR BINDING POTENCY AND USE THEREOF

Provided are: a compound represented by formula (I): (wherein ring A and ring D each represent a cyclic group which may have a substituent(s); E and G each represent a bond or a spacer having 1 to 8 atoms in its main chain; L represents a hydrogen atom or a substituent; X represents amino which may have a substituent(s), or a heterocylcic group which contains at least one nitrogen atom and which may have a substituent(s); n represents 0 to 3, in which when n is 2 or more, a plurality of ring A's may be the same or different from one another); a salt thereof; an N-oxide form thereof; a solvate thereof; a prodrug thereof; and a medicament which includes those. The compound represented by formula (I) is capable of binding S1P receptors (in particular, EDG-1 and/or EDG-6), and useful for preventing and/or treating rejection in transplantation, autoimmune diseases, allergic diseases, etc.

An improved procedure for the cyanation of aryl triflates: A convenient synthesis of 6-cyano-1,2,3,4-tetrahydroisoquinoline

A short synthesis of 6-cyano-1,2,3,4-tetrahydroisoquinoline is presented. The key step is an improved method of aryl triflate cyanation employing zinc(II)cyanide as the cyanide source.