53356-51-7

Usage

Uses

Used in Organic Synthesis:
2-(3,4-DIHYDROISOQUINOLIN-2(1H)-YL)ETHANAMINE is used as a building block in organic synthesis for the creation of various chemical compounds. Its unique structure allows it to be a versatile component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(3,4-DIHYDROISOQUINOLIN-2(1H)-YL)ETHANAMINE is used as a potential active pharmaceutical ingredient (API) for the development of new drugs. Its specific chemical properties may offer therapeutic benefits in the treatment of certain diseases or conditions.
Used in Chemical Research:
2-(3,4-DIHYDROISOQUINOLIN-2(1H)-YL)ETHANAMINE is also utilized in chemical research as a model compound to study the properties and reactions of amines and dihydroisoquinoline ring systems. This research can lead to a better understanding of the compound's potential applications and the development of new synthetic methods.

InChI:InChI=1/C11H16N2/c12-6-8-13-7-5-10-3-1-2-4-11(10)9-13/h1-4H,5-9,12H2

Upstream product

• 91349-97-2 2-(1,2,3,4-tetrahydroisoquinolin-2-yl)acetonitrile 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 2576-47-8 2-bromoethylamine hydrobromide 
• 689-98-5 chloroethylamine 
• 874942-10-6 tert-butyl (2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl)carbamate 
• 574-98-1 2-(2-bromoethyl)isoindoline-1,3-dione 
• 4498-67-3 1H-Indazole-3-carboxylic acid 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 758713-89-2 N-[2-(4-Benzylpiperidin-1-yl)ethyl]-N'-(2-methylquinolin-4-yl)pyrimidine-4,6-diamine 
• 758713-79-0 1-[2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-3-(3-nitrophenyl)urea 
• 1201219-10-4 perfluorophenyl 4-(4-(4-(5-(2-(3,4-dihydroisoquinolin-2(1H)-yl)ethylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl)benzoyl)benzamido)-1-methyl-1H-pyrrole-2-carboxylate 
• 1350977-89-7 N-(3-aminopropyl)-N-[2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonamide 
• 1350977-90-0 N-(3-aminopropyl)-N-[2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonamide fumarate 
• 1350977-88-6 N-[2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonamide hydrochloride 
• 61694-70-0 N-[2-(1,2,3,4-tetrahydro-2-isoquinolyl)-ethyl]-4-amino-5-chloro-2-methoxybenzamide 

Relevant academic research and scientific papers

8-[4-[2-(1,2,3,4-Tetrahydroisoquinolinyl)]butyl]-8-azaspiro[4.5]decane- 7,9-dione: A new 5-HT(1A) receptor ligand with the same activity profile as buspirone

A new analog of buspirone (1), i.e., 8-[4-[2-(1,2,3,4- tetrahydroisoquinolinyl)]butyl]-8-azaspiro-[4.5]decane-7,9-dione (6a), was synthesized. In was demonstrated that buspirone and its analog 6a were equipotent 5-HT(1A) ligands. Several behavioral models showed that 6a had essentially the same functional profile at 5-HT(1A) receptors as buspirone. The obtained results permit a conclusion that the basic nitrogen atom and terminal, bulky cycloimide moiety, but not the 2-pyrimidinyl group, of buspirone are directly involved in the formation of the bioactive complex with 5-HT(1A) receptors.

SAR Matrices Enable Discovery of Mixed Efficacy μ-Opioid Receptor Agonist Peptidomimetics with Simplified Structures through an Aromatic-Amine Pharmacophore

We previously described the development of potent μ-opioid receptor (MOR)-agonist/?-opioid receptor (DOR)-antagonist peptidomimetic ligands as an approach toward effective analgesics with reduced side effects. In this series, a tetrahydroquinoline (THQ) or substituted phenyl is employed to link two key pharmacophore elements, a dimethyltyrosine amino acid and typically an aromatic pendant. Using new and previously reported analogues, we constructed a structure-activity relationship (SAR) matrix that probes the utility of previously reported amine pendants. This matrix reveals that the MOR-agonist/DOR-antagonist properties of these ligands do not change when a tetrahydroisoquinoline (THIQ) pendant is used, despite removal of substituents on the core phenyl ring. Based on this observation, we retained the THIQ pendant and replaced the phenyl core with simpler aliphatic chain structures. These simpler analogues proved to be potent MOR-agonists with high variability in their effects at the DOR and the κ-opioid receptor (KOR). These data show that the amine of the THIQ pendant may be a novel pharmacophore element that favors high MOR-efficacy, whereas the aromatic ring of the THIQ pendant may produce high MOR-potency. Combined, the two pharmacophores within the THIQ pendant may be a structurally efficient means of converting opioid peptides and peptidomimetics into potent and efficacious MOR-agonists.

Impact of N-Alkylamino Substituents on Serotonin Receptor (5-HTR) Affinity and Phosphodiesterase 10A (PDE10A) Inhibition of Isoindole-1,3-dione Derivatives

In this study, a series of compounds derived from 4-methoxy-1H-isoindole-1,3(2H)-dione, potential ligands of phosphodiesterase 10A and serotonin receptors, were investigated as potential antipsychotics. A library of 4-methoxy-1H-isoindole-1,3(2H)-dione derivatives with various amine moieties was synthesized and examined for their phosphodiesterase 10A (PDE10A)-inhibiting properties and their 5-HT1A and 5-HT7 receptor affinities. Based on in vitro studies, the most potent compound, 18 (2-[4-(1H-benzimidazol-2-yl)butyl]-4-methoxy-1H-isoindole-1,3(2H)-dione), was selected and its safety in vitro was evaluated. In order to explain the binding mode of compound 18 in the active site of the PDE10A enzyme and describe the molecular interactions responsible for its inhibition, computer-aided docking studies were performed. The potential antipsychotic properties of compound 18 in a behavioral model of schizophrenia were also investigated.

Highly Selective Butyrylcholinesterase Inhibitors with Tunable Duration of Action by Chemical Modification of Transferable Carbamate Units Exhibit Pronounced Neuroprotective Effect in an Alzheimer's Disease Mouse Model

In this study, the carbamate structure of pseudo-irreversible butyrylcholinesterase (BChE) inhibitors was optimized with regard to a longer binding to the enzyme. A set of compounds bearing different heterocycles (e.g., morpholine, tetrahydroisoquinoline, benzimidazole, piperidine) and alkylene spacers (2 to 10 methylene groups between carbamate and heterocycle) in the carbamate residue was synthesized and characterized in vitro for their binding affinity, binding kinetics, and carbamate hydrolysis. These novel BChE inhibitors are highly selective for hBChE over human acetycholinesterase (hAChE), yielding short-, medium-, and long-acting nanomolar hBChE inhibitors (with a half-life of the carbamoylated enzyme ranging from 1 to 28 h). The inhibitors show neuroprotective properties in a murine hippocampal cell line and a pharmacological mouse model of Alzheimer's disease (AD), suggesting a significant benefit of BChE inhibition for a disease-modifying treatment of AD.

Neuroligin-2-derived peptide-covered polyamidoamine-based (PAMAM) dendrimers enhance pancreatic β-cells' proliferation and functions

Pancreatic β-cell membranes and presynaptic areas of neurons contain analogous protein complexes that control the secretion of bioactive molecules. These complexes include the neuroligins (NLs) and their binding partners, the neurexins (NXs). It has been recently reported that both insulin secretion and the proliferation rates of β-cells increase when cells are co-cultured with full-length NL-2 clusters. The pharmacological use of full-length protein is always problematic due to its unfavorable pharmacokinetic properties. Thus, NL-2-derived short peptide was conjugated to the surface of polyamidoamine-based (PAMAM) dendrimers. This nanoscale composite improved β-cell functions in terms of the rate of proliferation, glucose-stimulated insulin secretion (GSIS), and functional maturation. This functionalized dendrimer also protected β-cells under cellular stress conditions. In addition, various novel peptidomimetic scaffolds of NL-2-derived peptide were designed, synthesized, and conjugated to the surface of PAMAM in order to increase the biostability of the conjugates. However, after being covered by peptidomimetics, PAMAM dendrimers were inactive. Thus, the original peptide-based PAMAM dendrimer is a leading compound for continued research that might provide a unique starting point for designing an innovative class of antidiabetic therapeutics that possess a unique mode of action.

Solution-phase parallel synthesis of novel membrane-targeted antibiotics

The increase in the incidence of antibiotic-resistant infections is a major concern to healthcare workers and requires the development of novel antibacterial agents. Recently, we described a series of benzophenonecontaining antibiotics which displayed activity against antibiotic-resistant bacteria. We have shown that these agents function by disrupting the bacterial membrane. To further explore these compounds, a practical and efficient solution-phase parallel synthesis method was developed which allowed us to prepare combinatorial libraries of these agents. Using this method, we prepared 218 compounds in 58 reactions. All of the compounds were characterized by HPLC and MALDI-TOF mass spectrometry. Analysis of this library for antibacterial activity identified six compounds which displayed MTC values of 2.0 mg/T. against Staphylococcus aureus. Examination of the structure-function relationships of these agents revealed that cationic groups were required and that cyclic, aliphatic amines were crucial for activity. Using the information generated here, we speculate on how the various structural features of the molecule are necessary for the interaction with the bacterial membrane.

Electrooxidative cyclization of hydroquinolyl alcohols, hydroquinolylamines, and dimethyl aminomalonates

Several hydroquinolyl alcohols and amines were electrochemically oxidized in methanol in the presence of sodium methoxide and potassium iodide to afford the corresponding intramolecular cyclization products. Furthermore, several amino malonates were electrochemically oxidized to yield the corresponding heterocyclic compounds through an intramolecular carbon-carbon bond formation in the presence of sodium cyanide in methanol. CSIRO 2007.

SUBSTITUTED 2H-[1,2,4]TRIAZOLO[4,3-A]PYRAZINES AS GSK-3 INHIBITORS

The invention relates to compounds of formula (I) prodrugs thereof, and the pahrmaceutically acceptabel salts of the compounds and prodrugs, wherein Ra, Rb, R1 and R2 are as defined herein; pharmaceutical compositions thereof; and uses thereof.

Substituted 4-amino[1,2,4]triazolo[4,3-a] quinoxalines

The present invention provides compounds of formula (I) the prodrugs thereof, and the pharmaceutically acceptable salts of the compounds and prodrugs, wherein Ra, Rb, R1, and R2 are as defined herein; pharmaceutical compositions thereof; and uses thereof.

Conformationally-flexible benzamide analogues as dopamine D3 and σ2 receptor ligands

A series of conformationally-flexible analogues was prepared and their affinities for D2-like dopamine (D2, D3 and D 4) were determined using in vitro radioligand binding assays. The results of this structure-activity rela