73054-08-7

Upstream product

• 61-54-1 tryptamine 
• 100-07-2 4-methoxy-benzoyl chloride 
• 696-63-9 4-Methoxybenzenethiol 
• 201230-82-2 carbon monoxide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 13664-92-1 2,2-dibromo-1-(4-methoxyphenyl)ethanone 
• 343-94-2 tryptamine hydochloride 

Downstream Products

• 73053-84-6 3-(2-(4-methoxyphenyl)-5-oxazolyl)indole 
• 73053-95-9 N-(4-methoxybenzoyl)-β-oxotryptamine 

Relevant academic research and scientific papers

Cobalt catalysed aminocarbonylation of thiols in batch and flow for the preparation of amides

The synthesis of amides from thiols through a cobalt-catalyzed aminocarbonylation is shown. After optimizing all the reaction parameters, the methodology makes possible the obtention of amides with variable yields, while competing reactions such as the formation of disulfides and ureas can be limited. The process works well with aromatic thiols with electron donating groups (EDG) whereas other thiols give reaction with lower yields. The previous process has been transferred and optimized into flow equipment, thus allowing using less CO in a safer way, and permitting the scaling up of the synthesis. Two drugs, moclobemide and itopride were prepared with this methodology, albeit only in the second case with good results. A mechanistic pathway is proposed.

Cobalt-catalyzed aminocarbonylation of (hetero)aryl halides promoted by visible light

The catalytic aminocarbonylation of (hetero)aryl halides is widely applied in the synthesis of amides but relies heavily on the use of precious metal catalysis. Herein, we report an aminocarbonylation of (hetero)aryl halides using a simple cobalt catalyst under visible light irradiation. The reaction extends to the use of (hetero)aryl chlorides and is successful with a broad range of amine nucleophiles. Mechanistic investigations are consistent with a reaction proceeding via intermolecular charge transfer involving a donor-acceptor complex of the substrate and cobaltate catalyst.

Rational design of a new class of toll-like receptor 4 (tlr4) tryptamine related agonists by means of the structure- and ligand-based virtual screening for vaccine adjuvant discovery

In order to identify novel lead structures for human toll-like receptor 4 (hTLR4) modulation virtual high throughput screening by a peta-flops-scale supercomputer has been performed. Based on the in silico studies, a series of 12 compounds related to tryptamine was rationally designed to retain suitable molecular geometry for interaction with the hTLR4 binding site as well as to satisfy general principles of drug-likeness. The proposed compounds were synthesized, and tested by in vitro and ex vivo experiments, which revealed that several of them are capable to stimulate hTLR4 in vitro up to 25% activity of Monophosphoryl lipid A. The specific affinity of the in vitro most potent substance was confirmed by surface plasmon resonance direct-binding experiments. Moreover, two compounds from the series show also significant ability to elicit production of interleukin 6.

Potentiation of Francisella resistance to conventional antibiotics through small molecule adjuvants

A screen of 20 compounds identified small molecule adjuvants capable of potentiating antibiotic activity against Francisella philomiragia. Analogue synthesis of an initial hit compound led to the discovery of a potentially new class of small molecule adjuvants containing an indole core. The lead compound was able to lower the MIC of colistin by 32-fold against intrinsically resistant F. philomiragia.

An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin y

A novel synthetic methodology has been developed for the synthesis of dihydro-β-carboline derivatives employing oxidative amidation-Bischler- Napieralski reaction conditions using tryptamine and 2,2-dibromo-1- phenylethanone as key starting materials. A number of dihydro-β-carboline derivatives have been synthesized in moderate to good yields using this methodology. Attempts were made towards the conversion of these dihydro-β-carbolines to naturally occurring eudistomin alkaloids.

Nb-benzoyltryptamine derivatives with relaxant activity in guinea-pig ileum

A series of derivatives analogous to Nb-benzoyltryptamine were synthesized by the Schotten-Bauman procedure. The products obtained were: N b-4-methoxy-benzoyltryptamine, Nb-2,4-dimethoxy- benzoyltryptamine, Nb-3

Synthesis of Oxazolylindole Alkaloids from Tryptamine and Tryptophan by Oxidation with 2,3-Dichloro-5,6-dicyanobenzoquinone

When N-acyl derivatives of tryptamine and L-tryptophan methyl ester were treated with DDQ (2 equiv) in tetrahydrofuran or other anhydrous solvents, four consecutive reactions, dehydrogenation, nucleophilic cyclization, another dehydrogenation, and isomeri