406954-89-0

Upstream product

• 406954-88-9 N-(2,2-dimethoxyethyl)-N-(2-oxo-2-(2-(2-bromophenyl)ethylamino)ethyl)cyclohexanecarboxamide 
• 65185-58-2 2-(2-bromophenyl)ethanamine 
• 171734-72-8 toluene-4-sulfonic acid 2-(2-bromophenyl)ethyl ester 
• 75534-18-8 1-bromo-2-(2-chloro-ethyl)benzene 
• 1074-15-3 1-bromo-2-(2-bromoethyl)benzene 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 1372607-34-5 1-cyclohexanecarbonyl-3-methoxy-1,2-dihydropyrazine 
• 406954-90-3 (2,2-dimethoxyethyl)-[2-(2-bromophenyl)ethyl]amine 
• 32377-88-1 (cyclohexanecarbonyl-amino)-acetic acid 
• 406954-91-4 N-(2,2-dimethoxyethyl)-N-[2-(2-bromophenyl)ethyl]-2-(cyclohexylcarbonylamino)acetamide 
• 444815-17-2 N-[2-(2-bromophenyl)ethyl]formamide 
• 98-89-5 Cyclohexanecarboxylic acid 
• 406954-87-8 phenylmethyl 2-[N-(2,2-dimethoxyethyl)cyclohexylcarbonylamino]acetate 
• 60744-45-8 2-[N-(2,2-dimethoxyethyl)cyclohexylcarbonylamino]acetic acid 

Downstream Products

• 55268-74-1 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one 
• 59343-45-2 8-bromopraziquantel 
• 125273-86-1 2-(Cyclohexylcarbonyl)-2,3,6,7-tetrahydro-4H-pyrazino-<2,1-a>-isoquinolin-4-one 
• 94494-35-6 4-(cyclohexylcarbonyl)-3,4-dihydro-1-(2-phenylethyl)-2(1H)-pyrazinone 

Relevant academic research and scientific papers

A palladium-catalyzed intramolecular Heck/Hydrogenation approach towards the synthesis of praziquantel

Starting from 3-methoxy N-acylpyrazinium salts, a new approach towards the synthesis of the antischistosomal drug praziquantel (PZQ) has been developed. Utilization of a palladium-catalyzed intramolecular Heck reaction to form dehydro-PZQ followed by a Hydrogenation step, in a stepwise or one-pot manner, allowed for the gram scale synthesis of PZQ in 4 or 5 steps and in good overall yields. This methodology proved to be well suited for generating the pyrazino[1,2-a] isoindole and pyrazino[1,2-a] benzazepine analogues of PZQ.

Praziquantel derivatives with antischistosomal activity: Aromatic ring modification

A series of aromatic ring-modified praziquantel derivatives were prepared and evaluated against juvenile and adult stage of Schistosoma japonicumin. Several analogs comparable in activity to the drug praziquantel have been identified based on in vitro and in vivo japonuicum schistosomes worm viability assay. Structure and activity relationship of these praziquantel aromatic ring-modified compounds was revealed. Specifically, a compound in which a bromine has been introduced in the aromatic ring of praziquantel demonstrated close antischistosomal activity to praziquantel in vivo.

Amino acid derived heterocycles: Lewis acid catalyzed and radical cyclizations from peptide acetals

Bicyclization of peptide acetals via nucleophilic attack of a phenyl group on an endocyclic acyliminium ion 4 was explored as a route to novel amino acid derived heterocycles and peptidomimetic scaffolds. In the presence of protic acid, bridged structures such as 6 are formed readily from phenylalanine derivatives, but the fused-ring analogues 5 could not be obtained in good yield. In contrast, radical cyclization of the bromophenyl dihydropyrazinone 7 provides an effective alternative for the synthesis of 5 (n = 0, 1, 2). Additional versatility in this process was demonstrated by efficient synthesis of a different fused ring system, represented by the antihelmintic praziquantel, 8.