259263-97-3

Upstream product

• 51-67-2 tyrosamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 60-19-5 tyramine hydrochloride 

Downstream Products

• 388625-59-0 2-{2-[7-hydroxy-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-1-yl]-ethyl}-isoindole-1,3-dione 
• 1034139-59-7 C₂₁H₂₉NO₃SSi 
• 1315461-75-6 C₁₅H₁₇NO₄S 

Relevant academic research and scientific papers

Synthesis of nitrogen-containing fused-polycyclic compounds from tyramine derivatives using phenol dearomatization and cascade cyclization

We developed a novel method of synthesizing nitrogen-containing fused-polycyclic compounds using tyramine derivatives as substrates. The method is based on the dearomatization of phenols via an intramolecular ipso-Friedel-Crafts allenylation and sequentia

Syntheses, spectroscopic investigation and electronic properties of two sulfonamide derivatives: A combined experimental and quantum chemical approach

Two sulfonamides derivatives, N-phenethyl-4-methylbenzenesulfonamide (1) and N-(4-hydroxyphenethyl)-4-methylbenzenesulfonamide (2), were successfully synthesized and fully characterized using 1H NMR, 13C NMR, FT-IR spectroscopies and

Synthesis of Aporphine Analogues via Palladium-Catalyzed Intramolecular Aryl-Aryl Dehydrogenative Coupling

Reported herein is an intramolecular dehydrogenative coupling of two inert aryl C-H bonds for the synthesis of aporphine analogues. The process represents a novel tool for the preparation of aporphines via palladiun-catalyzed C-H bond activation. The present reaction is compatible with various functional groups, and the coupling products have been further applied for the synthesis of natural products aporphine and zenkerine.

Monoligated Pd(0)-catalyzed intramolecular ortho- and para-arylation of phenols for the synthesis of aporphine alkaloids. Synthesis of (-)-lirinine

An intramolecular palladium(0)-mediated ortho-arylation of phenols applied to the synthesis of various substituted aporphines is reported. Most significantly, the efficiency of the transformation was enhanced by the use of monoligated Pd(0) complexes. This methodology was extended to para-arylation of phenols and employed in the synthesis of the aporphine alkaloid (-)-lirinine.

Flexible synthesis of montanine-like alkaloids: Revisiting the structure of montabuphine

An efficient and stereocontrolled synthetic strategy towards the synthesis of montanine-like alkaloids was developed. Our results suggest that the structure elucidation for natural montabuphine needs further elaboration.

Cosmetic or dermopharmaceutical compositions comprising tyramine derivatives, method for preparing same, and use thereof

The invention concerns cosmetic or dermopharmaceutical compositions comprising tyramine derivatives and their salts. The invention also concerns the method for preparing same and use thereof for reducing pigmaentation.

Synthesis of (±)-aporphine utilizing Pictet-Spengler and intramolecular phenol ortho-arylation reactions

A synthesis of the alkaloid (±)-aporphine is reported. The initial key step of the synthesis involves a Pictet-Spengler cyclization of N-tosyl tyramine with 2-bromophenylacetaldehyde in trifluoroacetic acid. This step was followed by the second strategic

Parallel synthesis and biological activity of a new class of high affinity and selective δ-opioid ligand

A considerable number of research papers describing the synthesis and testing of the delta opioid receptor (DOR) ligands, SNC-80 and TAN-67, and analogues of these two compounds, have been published in recent years. However, there have been few reports of the discovery of completely new structural classes of selective DOR ligand. By optimising a hit compound identified by high throughput screening, a new series of tetrahydroisoquinoline sulphonamide-based delta opioid ligands was discovered. The main challenge in this series was to simultaneously improve both affinity and physicochemical properties, notably aqueous solubility. The most active ligand had an affinity (IC50) of 6 nM for the cloned human DOR, representing a 15-fold improvement relative to the original hit 1 (IC50 98 nM). Compounds from this new series show good selectivity for the DOR over μ and κ opioid receptors. However the most active and selective compounds had poor aqueous solubility. Improved aqueous solubility was obtained by replacing the phthalimide group in 1 by basic groups, allowing the synthesis of salt forms. A series of compounds with improved affinity and solubility relative to 1 was identified and these compounds showed activity in an in vivo model of antinociception, the formalin paw test. In the case of compound 19, this analgesic activity was shown to be mediated primarily via a DOR mechanism. The most active compound in vivo, 46, showed superior potency in this test compared to the reference DOR ligand, TAN-67 and similar potency to morphine (68% and 58% inhibition in Phases 1 and 2, respectively, at a dose of 10 mmol/kg i.v.).