5596-87-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(3,4-Dihydroisoquinolin-2(1H)-yl)propan-1-amine is used as a drug candidate for the development of pharmaceutical drugs due to its potential therapeutic properties. Its unique chemical structure and properties may contribute to the discovery of new treatments for various medical conditions.
Used in Medicinal Chemistry Research:
3-(3,4-Dihydroisoquinolin-2(1H)-yl)propan-1-amine is used as a research compound in medicinal chemistry to explore its potential applications and properties. Scientists and researchers are investigating its interactions with biological targets and its potential to modulate specific pathways or processes, which could lead to the development of new therapeutic agents.

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 5460-29-7 2-(3-bromopropyl)isoindole-1,3-dione 
• 14753-26-5 3-chloropropan-1-amine 
• 198895-33-9 2-[3-(1,2,3,4-tetrahydroisoquinolin-2-yl)propyl]-2,3-dihydro-1H-isoindole-1,3-dione 

Downstream Products

• 1350977-94-4 N-(3-aminopropyl)-N-[3-(1,2,3,4-tetrahydroisoquinolin-2-yl)propyl]benzenesulfonamide fumarate 
• 1350977-93-3 N-(3-aminopropyl)-N-[3-(1,2,3,4-tetrahydroisoquinolin-2-yl)propyl]benzenesulfonamide 
• 1351184-57-0 N-(2-aminoethyl)-N-[3-(1,2,3,4-tetrahydroisoquinolin-2-yl)propyl]benzenesulfonamide 
• 1201219-09-1 perfluorophenyl 4-(4-(4-(5-(3-(3,4-dihydroisoquinolin-2(1H)-yl)propylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl)benzoyl)benzamido)-1-methyl-1H-pyrrole-2-carboxylate 

Relevant academic research and scientific papers

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.

INHIBITORS OF BACTERIAL GLYCOSYL TRANSFERASES

Described herein are compounds of Formula (I'), Formula (IA), Formulae (I)-(VII), pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, and prodrug sthereof. The invention also provides pharmaceutical compositions of the compounds for human and veterinary use. Compounds of the present invention are useful for inhibiting bacterial growth and therefore are useful in treating and/or preventing bacterial infections. Methods of using the compounds for treating and/or preventing a bacterial infection in a subject are also described.

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.

Synthesis and evaluation of novel N-substituted-6-methoxynaphthalene-2- carboxamides as potential chemosensitizing agents for cancer

A novel class of molecules with structure N-[3-(heteroaryl)propyl]-6- methoxynaphthalene-2-carboxamides 8-13 were synthesized by condensing 6-methoxy-2-naphthoyl chloride 1 with 3-(heteroaryl)propyl amines 2-7. Compounds 8-12 were evaluated in vitro, in P388 murine lymphocytic leukemia cell line (P388) using SRB assay for cytotoxicity and in adriamycin resistant P388 murine lymphocytic leukemia cell line (P388/ADR) using MTT assay for resistant reversal activity. Compounds 8-12 were non-toxic at lower dose of 20 μg/ml, and effectively reversed adriamycin resistance. However, at higher doses (40, 80 μg/ml) they showed significant cytotxicity and hence reversal potency was not determined at these concentrations.

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.

Aminopyridazines as acetylcholinesterase inhibitors

Following the discovery of the weak, competitive and reversible acetylcholinesterase (AChE)-inhibiting activity of minaprine (3c) (IC50 = 85 μM on homogenized rat striatum AChE), a series of 3-amino-6- phenylpyridazines was synthesized and tested for inhibition of AChE. A classical structure-activity relationship exploration suggested that, in comparison to minaprine, the critical elements for high AChE inhibition are as follows: (i) presence of a central pyridazine ring, (ii) necessity of a lipophilic cationic head, (iii) change from a 2- to a 4-5-carbon units distance between the pyridazine ring and the cationic head. Among all the derivatives investigated, 3-[2-(1-benzylpiperidin-4-yl)ethylamino]-6- phenylpyridazine (3y), which shows an IC50 of 0.12 μM on purified AChE (electric eel), was found to be one of the most potent anti-AChE inhibitors, representing a 5000-fold increase in potency compared to minaprine.