166398-33-0

Basic information

• Product Name: tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate
• Synonyms: tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate;tert-Butyl 6-cyano-1,2,3,4-tetrahydroisoquinoline-2-carboxylate;2-BOC-6-CYANO-3,4-DIHYDROISOQUINOLINE;tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate-12;2(1H)-Isoquinolinecarboxylic acid, 6-cyano-3,4-dihydro-, 1,1-dimethylethyl ester
• CAS NO: 166398-33-0
• Molecular Formula: C₁₅H₁₈N₂O₂
• Molecular Weight: 258.32
• Mol File: 166398-33-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 386.817 °C at 760 mmHg
• Flash Point: 187.74 °C
• Appearance: /
• Density: 1.163 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate(166398-33-0)
• EPA Substance Registry System: tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate(166398-33-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 166398-33-0(Hazardous Substances Data)

Usage

General Description

Tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate is a chemical compound derived from isoquinoline and carboxylic acid. It is known for its role in chemical synthesis as a building block in the creation of various pharmaceuticals, agrochemicals, and materials. The tert-butyl group attached to the molecule is commonly used to enhance the compound's stability and solubility, making it easier to handle and store. The cyano group and the dihydroisoquinoline ring structure contribute to its unique chemical properties, allowing for a wide range of potential applications in organic synthesis. Additionally, the carboxylate group enables the compound to form coordination complexes with metal ions, thus serving as a versatile ligand in various catalytic 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 
• 893566-74-0 6-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline 
• 226942-29-6 6-bromo-1,2,3,4-tetrahydroisoquinoline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 166398-34-1 1,2,3,4-tetrahydroisoquinoline-6-carbonitrile 
• 158984-84-0 6-trifluoromethanesulfonyloxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 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

• 166398-34-1 1,2,3,4-tetrahydroisoquinoline-6-carbonitrile 
• 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 
• 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 
• 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 
• 1286750-76-2 sodium 3-(6-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydroisoquinolin-2(1H)-yl)propanoate 
• 1286751-29-8 ethyl 3-(6-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydroisoquinolin-2(1H)-yl)propanoate 
• 1286751-25-4 2-isopropoxy-5-(3-(1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)benzonitrile trifluoroacetate 
• 1286751-23-2 tert-butyl 6-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 

Relevant articles and documents

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.

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.

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.