15889-92-6

Upstream product

• 96-48-0 4-butanolide 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 4230-93-7 3,4-dimethoxynitrostyrene 

Downstream Products

• 55716-88-6 N-[2-(3,4-dimethoxyphenyl)ethyl]-2-pyrrolidone 
• 15889-93-7 (+/-)-crispine A 

Relevant academic research and scientific papers

First enantioselective synthesis of the antitumour alkaloid (+)-crispine a and determination of its enantiomeric purity by 1H NMR

A simple enantioselective synthesis of the pyrrolo[2,1-a]isoquinoline alkaloid (+)-crispine A, based on the use of an asymmetric transfer hydrogenation as the key step, is described. The enantiomeric excesses of the obtained alkaloid samples were determin

Dual Nicotinic Acetylcholine Receptor α4β2 Antagonists/α7 Agonists: Synthesis, Docking Studies, and Pharmacological Evaluation of Tetrahydroisoquinolines and Tetrahydroisoquinolinium Salts

We describe the synthesis of tetrahydroisoquinolines and tetrahydroisoquinolinium salts together with their pharmacological properties at various nicotinic acetylcholine receptors. In general, the compounds were α4β2 nAChR antagonists, with the tetrahydroisoquinolinium salts being more potent than the parent tetrahydroisoquinoline derivatives. The most potent α4β2 antagonist, 6c, exhibited submicromolar binding Ki and functional IC50 values and high selectivity for this receptor over the α4β4 and α3β4 nAChRs. Whereas the (S)-6c enantiomer was essentially inactive at α4β2, (R)-6c was a slightly more potent α4β2 antagonist than the reference β2-nAChR antagonist DHβη. The observation that the α4β2 activity resided exclusively in the (R)-enantiomer was in full agreement with docking studies. Several of tetrahydroisoquinolinium salts also displayed agonist activity at the α7 nAChR. Preliminary in vivo evaluation revealed antidepressant-like effects of both (R)-5c and (R)-6c in the mouse forced swim test, supporting the therapeutic potential of α4β2 nAChR antagonists for this indication.

Design, synthesis, and biological evaluation of Erythrina alkaloid analogues as neuronal nicotinic acetylcholine receptor antagonists

The synthesis of a new series of Erythrina alkaloid analogues and their pharmacological characterization at various nicotine acetylcholine receptor (nAChR) subtypes are described. The compounds were designed to be simplified analogues of aromatic erythrinanes with the aim of obtaining subtype-selective antagonists for the nAChRs and thereby probe the potential of using these natural products as scaffolds for further ligand optimization. The most selective and potent nAChR ligand to come from the series, 6,7-dimethoxy-2- methyl-1,2,3,4-tetrahydroisoquinoline (3c) (also a natural product by the name of O-methylcorypalline), displayed submicromolar binding affinity toward the α4β2 nAChR with more than 300-fold selectivity over α4β4, α3β4, and α7. Furthermore, this lead structure (which also has inhibitory activity at monoamine oxidases A and B and at the serotonin and norepinephrine transporters) showed antidepressant-like effect in the mouse forced swim test at 30 mg/kg.

A template-based mnemonic for monoamine oxidase (MAO-N) catalyzed reactions and its application to the chemo-enzymatic deracemisation of the alkaloid (±)-crispine A

A template-based mnemonic has been developed for the enzyme monoamine oxidase from Aspergillus niger and has been used to successfully identify the alkaloid (±)-crispine A as a target for chemo-enzymatic deracemisation yielding the biologically active (R)

Photosolvolysis of Bridgehead Quaternary Ammonium Salts.I. Synthesis of Some 3-Benzazonine Derivatives

The medium-ring heterocyclic derivative 7,9,10-trimethoxy-3-methyl-2,3,4,5,6,7-hexahydro-1H-3-benzazonine (10a) was obtained from the ultraviolet irradiation of the reduced pyrroloisoquinolinium iodide salt (9a) in methanol, along with N-2-(3,4-di