99746-73-3

Usage

Uses

Used in Chiral Station Phases Synthesis:
(S)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one is used as an intermediate in the synthesis of perphenylcarbamated β-cyclodextrin based chiral stationary phases. These phases are essential for the separation of enantiomers in high-performance liquid chromatography (HPLC), a technique widely used in pharmaceutical, chemical, and environmental analysis to determine the purity and composition of chiral compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-2,3,6,7-Tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one is used as the inactive enantiomer of praziquantel, which is relevant for research purposes. Praziquantel is an anthelmintic drug used to treat various parasitic infections, and the study of its inactive enantiomer can provide valuable insights into the development of more effective and selective drugs.

Upstream product

• 210223-97-5 2-[(2,2-dimethoxyethyl)amino]-N-(2-phenylethyl)acetamide hydrochloride 
• 64-04-0 phenethylamine 
• 13156-95-1 2-chloro-N-phenethylacetamide 
• 1622136-46-2 (S)-praziquanamine-hemi-dibenzoyl-D-tataric acid salt 
• 61196-37-0 2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 
• 55268-74-1 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one 
• 1558003-70-5 (S)-(+)-2-((S)-2-(6-methoxynaphthalen-2-yl)propanoyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 99700-59-1 C₂₂H₂₁F₃N₂O₃ 

Downstream Products

• 99780-88-8 (-)-1,3,4,6,7,11b-Hexahydro-2H-pyrazino<2,1-a>isochinolin 
• 99780-87-7 (+)-1,3,4,6,7,11b-Hexahydro-2H-pyrazino<2,1-a>isochinolin 
• 134924-72-4 (+)-2-(4-trans-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 134924-70-2 (+)-2-(4-cis-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 57452-97-8 (+)-Praziquantel 
• 135526-78-2 (-)-Praziquantel 
• 55375-92-3 (R)-(-)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 61196-37-0 2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 
• 57452-32-1 (+)-2-(4-oxocyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 

Relevant academic research and scientific papers

One-pot palladium-catalyzed racemization of (S)-praziquanamine: A key intermediate for the anthelmintic agent (R)-praziquantel

An one-pot palladium-catalyzed procedure for racemization of (S)-praziquanamine, which is the undesired enantiomer and produced during the resolution step for preparing the anthelmintic drug (R)-praziquantel, has been developed through dehydrogenation of

Optically active [...][...] and the corresponding method for the preparation of the

The invention provides a preparation method of pyrazino amine salt with optical activity. The preparation method is characterized in that pyrazino amine salt is prepared through the reaction of racemic pyrazino amine and dibenzoyltartaric acid with optical activity in the presence of a solvent, wherein the solvent comprises more than 50% of 2-butanone in volume fraction; and dibenzoyltartaric acid with optical activity is diphenyl diketone-L-tartaric acid with optical impurity not less than 95%, or diphenyl diketone-D-tartaric acid with optical impurity not less than 95%. The invention also provides a preparation method of corresponding pyrazino amine with optical activity. The method performed for separating racemic pyrazino amine is very suitable for industrial application.

Development of chiral praziquantel analogues as potential drug candidates with activity to juvenile Schistosoma japonicum

A series of chiral praziquantel analogues were synthesized and evaluated against Schistosoma japonicum both in vitro and in vivo. All compounds exhibited low to considerable good activity in vivo. Remarkably, worm reduction rate of R-3 was 60.0% at a sing

Design and synthesis of molecular probes for the determination of the target of the anthelmintic drug praziquantel

Schistosomiasis is a highly prevalent neglected tropical disease caused by blood-dwelling helminths of the genus Schistosoma. Praziquantel (PZQ) is the only drug available widely for the treatment of this disease and is administered in racemic form, even

A straightforward and efficient synthesis of praziquantel enantiomers and their 4′-hydroxy derivatives

A new method for the synthesis of praziquantel enantiomers via resolution of praziquanamine with (S)-(+)-naproxen was developed. The four 4′-hydroxy derivatives were obtained through each single praziquanamine enantiomer, coupling with cis- and trans-4-(benzyloxy)cyclohexanecarboxylic acids and subsequent hydrogenolysis for the deprotection of the 4′-OH cyclohexane residue. Additionally, the in vitro cysticidal activity of the compounds was tested, finding that (R)-(-)-praziquantel is the eutomer.

Synthesis of "Trioxaquantel" derivatives as potential new antischistosomal drugs

Over the past 20 years, praziquantel, a pyrazinoisoquinoline derivative, has become the mainstay for morbidity control of human and animal schistosomiasis. From early in their lives in vertebrate hosts, schistosomes ingest hemoglobin and aggregate the released heme as a dark pigment very similar to the hemozoin produced by Plasmodium in malaria infection. The antimalarial artemisinin derivatives have real, though low, schistosomicide activity. Because of the complementarity of the two drug classes - praziquantel and artemisinin derivatives - we designed new molecules, named trioxaquantels, that combine the 1,2,4-trioxane unit responsible for the activity of artemisinin, and the pyrazinoisoquinoline moiety of praziquantel within a single drug. The synthesis of these new drugs and their preliminary evaluation in mice infected with Schistosoma mansoni is reported here. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.