81185-19-5

Upstream product

• 5309-19-3 8-methoxy-2-tetralone 
• 100-46-9 benzylamine 
• 5309-18-2 1,7-dimethoxynaphthalene 
• 6342-77-4 2-methoxy-benzenepropanoic acid 
• 22955-75-5 3-(2-methoxyphenyl)propionyl chloride 
• 135-02-4 ortho-anisaldehyde 
• 90266-01-6 1-diazo-4-(2'-methoxyphenyl)butan-2-one 
• 1011-54-7 2-methoxycinnamic acid 
• 575-38-2 1,7-Dihydroxynaphthalene 

Downstream Products

• 3880-77-1 8-methoxy-2-aminotetralin 
• 81185-18-4 Benzyl-(8-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine 
• 81185-18-4 Benzyl-(8-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine 
• 3894-47-1 (8-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine; hydrochloride 
• 3894-47-1 (8-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine; hydrochloride 
• 76135-31-4 (-)-8-hydroxy-2-(di-n-propylamino)tetralin*HBr 
• 76135-31-4 (+)-8-hydroxy-2(di-N-propylamino)-tetralin hydrobromide 

Relevant academic research and scientific papers

Synthesis and evaluation of two new candidate high-affinity full agonist PET radioligands for imaging 5-HT1B receptors

Introduction: The serotonin 1B receptor subtype is of interest in the pathophysiology and treatment of depression, anxiety, and migraine. Over recent years 5-HT1B receptor binding in human brain has been examined with PET using radioligands that are partial but not full agonists. To explore how the intrinsic activity of a PET radioligand may affect imaging performance, two high-affinity full 5-HT1B receptor agonists (AZ11136118, 4; and AZ11895987, 5) were selected from a large compound library and radiolabeled for PET examination in non-human primates. Methods: [11C]4 was obtained through Pd(0)-mediated insertion of [11C]carbon monoxide between prepared iodoarene and homochiral amine precursors. [11C]5 was obtained through N-11C-methylation of N-desmethyl precursor 6 with [11C]methyl triflate. [11C]4 and [11C]5 were studied with PET in rhesus or cynomolgus monkey. [11C]4 was studied with PET in mice and rats to measure brain uptake and specific binding. Ex-vivo experiments in rats were performed to identify whether there were radiometabolites in brain. Physiochemical parameters for [11C]4 (pKa, logD and conformational energetics) were evaluated. Results: Both [11C]4 and [11C]5 were successfully produced in high radiochemical purity and in adequate amounts for PET experiments. After intravenous injection of [11C]4, brain radioactivity peaked at a low level (0.2 SUV). Pretreatment with tariquidar, an inhibitor of the brain P-gp efflux transporter, increased brain exposure four-fold whereas pretreatment with a high pharmacological dose of the 5-HT1B antagonist, AR-A000002, had no effect on the binding. Ex-vivo experiments in rats showed no radiometabolites entering brain. [11C]5 also failed to enter monkey brain under baseline conditions. Conclusions: [11C]4 and [11C]5 show too low brain uptake and specific binding to be useful PET radioligands. Low brain uptake is partly ascribed to efflux transporter action as well as unfavorable conformations.

Synthesis and antifungal activities of novel 2-aminotetralin derivatives

Novel 2-aminotetralin derivatives were synthesized as antifungal agents. The 2-aminotetralin scaffold was chemically designed to mimic the tetrahydroisoquinoline ring of the lead molecule described before. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Compounds 10a, 12a, 12c, 13b, and 13d are more potent than fluconazole against seven testing human fungal pathogens. Compound 10b exhibits much higher antifungal activities against all of the four fluconazole-resistant clinic Candida albicans strains than the control drugs including amphotericin B, terbinafine, ketoconazole, and itraconazole. The mode of action of some compounds to the potential receptor lanosterol 14α-demethylase (CYP51) was investigated by molecular docking. The studies presented here provide a new structural type for the development of novel antifungal compounds. Furthermore, 10b was evaluated in vivo by a rat vaginal candidiasis model, and it was found that 10b significantly decreases the number of fungal colony counts.

2-Amido-8-methoxytetralins: A Series of Nonindolic Melatonin-like Agents

A series of unsubstituted and methoxy-substituted 2-amidotetralins (4a-q) was prepared and evaluated for their ability to complete for 2-iodomelatonin binding to chicken retinal membranes and for their potency to inhibit the calcium-dependent release of dopamine from rabbit retina.The lead compound, 2-acetamido-8-methoxytetralin (4j), showed a moderate affinity (Ki = 46 nM) and potency (IC50 = 1.4 nM) at the melatonin receptor.The structural requirements necessary for optimal agonistic activity at the melatonin receptor are as follows.First, the amido group, which should have a small, nonbranched alkyl group, is essential for affinity, and second, the methoxy substituent at the 8-position of the 2-amidotetralin ring is essential for optimal agonistic activity at the melatonin receptor.We concluded that this series of unsubstituted and methoxy-substituted 2-amidotetralins constitutes a class of nonindolic melatonin-like agents that can be used as pharmacological tools to further characterize melatonin receptors and to elucidate the mode of action of melatonin.

Novel compounds for the treatment of migraine

This invention relates to novel 8-methoxy-2-amino-1,2,3,4-tetrahydronaphthalenes, to the methods for their preparation and to their use in the treatment of migraine and related disorders.