57894-18-5

Upstream product

• 37627-79-5 N-[2-(3-methoxy-4-hydroxy-phenyl)ethyl]phthalimide 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 121-33-5 vanillin 
• 62-31-7 dopamine hydrochloride 
• 36169-26-3 N-<2-(3,4-methylenedioxyphenyl)ethyl>phthalimide 
• 85-44-9 phthalic anhydride 
• 26477-09-8 N-2-(3,4-dimethoxyphenyl)ethylphthalimide 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 51-61-6 dopamine 

Downstream Products

• 51-61-6 dopamine 
• 129024-87-9 (4Z,7Z,10Z,13Z,16Z,19Z)-N-(3,4-dihydroxyphenethyl)docosa-4,7,10,13,16,19-hexaenamide 
• 1351951-84-2 d₆-N-[2-(3,4-dimethoxy-phenyl)ethyl]formamide 
• 1162658-07-2 d₆-2-(3,4-dimethoxyphenyl)ethanamine 

Relevant academic research and scientific papers

METHODS AND INTERMEDIATES FOR PREPARING DEUTETRABENAZINE

Disclosed is a process for the preparation of deutetrabenazine and intermediates useful in the preparation thereof. Disclosed are also process for making amorphous deutetrabenazine.

Novel synthesis of isoindoline/isoindoline-1,3-dione derivatives under solventless conditions and evaluation with the human D2 receptor

Isoindolines are the focus of much research because of being an important family of compounds present in a wide array of bioactive molecules. Although many different pathways of synthesis have been described, they do not follow green chemistry principles. The aim of this contribution was to develop a green synthesis technique for isoindolines/dioxoisoindolines. These compounds derived from analogs of important biogenic amines were tested in silico (on the human dopamine receptor D2) to predict their affinities and some pharmacokinetic parameters. One of them, YaI-01, was evaluated in vivo in a Parkinsonism mouse model. Seven molecules, including three isoindolines and four dioxoisoindolines, were synthesized using simple heating and relatively quick solventless reactions. They were then purified with a methodology as green as possible. Since no published crystal structure exists for dopamine receptor D2, it was necessary to generate and validate a homology model for molecular docking studies of the seven molecules synthesized presently. Docking was performed to assess affinity in terms of binding energy (?G). Apart from pharmacokinetic parameters, Lipinski’s rule of five and some properties of toxicity from QSAR models were evaluated. Whereas no risk was found for the isoindolines, there was evidence of three kinds of toxicity for the isoindoline-1,3-dione compounds. Overall, the in silico analysis suggests that the three isoindolines herein tested have the best properties as ligands of the dopamine receptor D2, interacting with the main amino acid residues at its allosteric binding site. YaI-01 (254 μmol/kg) reverted Parkinsonism induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine.

Difluoromethylthiolation of Phenols and Related Compounds with a HF2CSO2Na/Ph2PCl/Me3SiCl System

A novel HF2CSO2Na/Ph2PCl/Me3SiCl system is disclosed for the late-stage direct difluoromethylthiolation of Csp2 and Csp3 nucleophiles. Difluoromethylthiolation of phenols and naphthols proceeded nicely under this system to regioselectively provide corresponding SCF2H compounds in good yields. Other substrates such as indoles, pyrroles, pyrazoles, enamines, ketones, and β-keto esters were also transformed to corresponding SCF2H products in good yields. The late-stage direct difluoromethylthiolation of a number of natural products and pharmaceutically attractive molecules was also achieved.

Near infrared-caged D-amino acids multifunctional assembly for simultaneously eradicating biofilms and bacteria

A nanodevice composed of an upconverting nanoparticle (UCNP) core and a thin TiO2 shell surface modified with d-amino acids was designed. Due to the UCNP core, NIR light can be converted to high-energy UV photons. As a consequence, UV light can

Mussel-inspired green synthesis of silver nanoparticles on graphene oxide nanosheets for enhanced catalytic applications

We report a facile green approach to the synthesis of silver nanoparticles (Ag NPs) on the surface of graphene oxide nanosheets functionalized with mussel-inspired dopamine (GO-Dopa) without additional reductants or stabilizers at room temperature. The resulting hybrid Ag/GO-Dopa exhibits good dispersity and excellent catalytic activity in the reduction of nitroarenes.

Method of synthesizing acetonide-protected catechol-containing compounds and intermediates produced therein

The inventors disclose here a novel, facile approach to the synthesis of acetonide-protected catechol-containing compounds having at least one amine group. In specific embodiments, the invention provides novel methods of synthesizing 3,4-dihydroxyphenylalanine (H-DOPA(acetonide)-OH (6)), Fmoc-protected H-DOPA(acetonide)-OH (Fmoc-DOPA(acetonide)-OH (7)), Fmoc-protected dopamine (Fmoc-dopamine(acetonide) (10)), TFA-protected dopamine (TFA-dopamine(acetonide) (13)) and acetonide-protected 4-(2-aminoethyl)benzene-1,2-diol (acetonide-protected dopamine (14)).

Structural study on solvates of dopamine-based cyclic imide derivatives

A structural study on two dopamine-based imide derivatives, namely, 2-(3,4-dihydroxyphenethyl)isoindole-1,3-dione (1) and 2,6-bis-[2-(3,4- dihydroxyphenyl)ethyl]pyrrolo [3,4-f]isoindole-1,3,5,7-tetrone (2), and their solvates was carried out. The compound 1 (Z′ = 2) was crystallized through a melt crystallization process, whereas its two solvates (Z′ = 1 of each), containing one water molecule (1a) and the other containing two quinoline molecules (1b) in their crystal lattices, respectively, were obtained through solution crystallization. The reasons for Z′ = 2 arising from symmetry nonequivalent molecules in the unit cell of 1 is attributed to the nonparallel arrangement of two layers of self-assembled molecules in crystal lattice, where one layer has C-H???π and another layer has C=O???π interactions. Four different solvates of compound 2 (Z′ = 0.5 of each), containing two DMF molecules (2a), two DMSO molecules (2b), two pyridine molecules (2c), and six quinoline molecules (2d), were also obtained through solution crystallization of 2 in respective solvents. Solvate 2d has channels in its structure which are formed by interaction of 2 with quinoline molecules through O-H???N and C-H???π interactions. Additional quinoline molecules reside in these channels of approximately (11 × 12) A dimension. Structural features of all the compounds and their solvates have been studied by single crystal X-ray structures, powder X-ray diffractions (PXRD), thermogravimetric analyses (TGA), and differential scanning calorimetric (DSC) measurements.

Bronsted acid assisted activation of imide carbonyl group: Regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine

Activation of imide carbonyl group with trifluoromethanesulfonic acid facilitates the intramolecular cyclization of phenethylphthalimides to give a fused isoindoloisoquinolinone skeleton. The first one pot regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine has been successfully executed using this methodology.

An unusual reactivity of BBr3: Accessing tetrahydroisoquinoline units from N-phenethylimides

Isoindoloisoquinalinone, pyrroloisoquinolinone and benzo[a]quinolizinone units are constructed via intramolecular cyclization of the methoxy substituted N-phenethylimides using BBr3.

Acetonide protection of dopamine for the synthesis of highly pure N-docosahexaenoyldopamine

Direct acetonide protection of the catechol of dopamine has proven to be problematic due to the formation of Pictet-Spengler isoquinolines. Here we report an efficient method for acetonide protection of dopamine, allowing the preparation of a dopamine prodrug without complications from the Pictet-Spengler reaction. Acetonide-protected dopamine was first synthesized by pre-protecting the amino group with phthaloyl followed by refluxing with 2,2-dimethoxypropane in the presence of TsOH. Further work demonstrated that Fmoc and trifluoroacetyl were also suitable N-protective groups, while Boc-protected dopamine gave an isoquinoline product. Acetonide-protected dopamine was coupled to DHA (all cis-4,7,10,13,16,19-docosahexaenoic acid) to produce the N-DHA-dopamine prodrug with high purity.