57452-97-8

Basic information

• Product Name: d-Praziquantel
• Synonyms: (S)-(+)-Praziquantel;4H-Pyrazino[2,1-a]isoquinolin-4-one, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-, (11bS)- (9CI);4H-Pyrazino[2,1-a]isoquinolin-4-one, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-, (S)-;d-Praziquantel;(11bS)-2-(Cyclohexylcarbonyl)-1,2,3,6,7,11B-Hexahydro-4H-Pyrazino[2,1-a]Isoquinolin-4-One;ZINC00403566;(S)-2-(Cyclohexanecarbonyl)-2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one
• CAS NO: 57452-97-8
• Molecular Formula: C₁₉H₂₄N₂O₂
• Molecular Weight: 312.40606
• Mol File: 57452-97-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly, Sonicated), Ethanol (Slightly, Sonicated)
• CAS DataBase Reference: d-Praziquantel(CAS DataBase Reference)
• NIST Chemistry Reference: d-Praziquantel(57452-97-8)
• EPA Substance Registry System: d-Praziquantel(57452-97-8)

Safety Data

• Hazardous Substances Data: 57452-97-8(Hazardous Substances Data)

Usage

Uses

(S)-Praziquantel is used in the synthetic preparation of perphenylcarbamated β-cyclodextrin based chiral stationary phases via thiol-ene click chemistry for HPLC enantioseparations. (S)-Praziquantel is also the inactive enantiomer of praziquantel regarding activity against juvenile S. mansoni infestations in mice.

InChI:InChI=1S/C19H24N2O2/c22-18-13-20(19(23)15-7-2-1-3-8-15)12-17-16-9-5-4-6-14(16)10-11-21(17)18/h4-6,9,15,17H,1-3,7-8,10-13H2/t17-/m1/s1

Upstream product

• 55268-74-1 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one 
• 99746-73-3 (S)-(-)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 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 
• 61196-37-0 2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 
• 850130-96-0 2-(4-methoxyphenyl)-1-(nitromethyl)-1,2,3,4-tetrahydroisoquinoline 
• 78317-83-6 2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 60567-47-7 (S)-1-[(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)]cyclohexanecarboxylic acid amide 
• 79-04-9 chloroacetyl chloride 
• 1447933-71-2 1-(R)-(N-cyclohexylcarboxamidomethyl)-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 1447933-67-6 1-(R)-(aminomethyl)-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 1132765-82-2 1-(aminomethyl)-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 135526-78-2 (-)-Praziquantel 
• 55268-74-1 2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one 

Relevant articles and documents

Preparation of a novel bridged bis(β-cyclodextrin) chiral stationary phase by thiol-ene click chemistry for enhanced enantioseparation in HPLC

A bridged bis(β-cyclodextrin) ligand was firstly synthesized via a thiol-ene click chemistry reaction between allyl-ureido-β-cyclodextrin and 4-4′-thiobisthiophenol, which was then bonded onto a 5 μm spherical silica gel to obtain a novel bridged bis(β-cyclodextrin) chiral stationary phase (HTCDP). The structures of HTCDP and the bridged bis(β-cyclodextrin) ligand were characterized by the 1H nuclear magnetic resonance (1H NMR), solid state 13C nuclear magnetic resonance (13C NMR) spectra spectrum, scanning electron microscope, elemental analysis, mass spectrometry, infrared spectrometry and thermogravimetric analysis. The performance of HTCDP in enantioseparation was systematically examined by separating 21 chiral compounds, including 8 flavanones, 8 triazole pesticides and 5 other common chiral drugs (benzoin, praziquantel, 1-1′-bi-2-naphthol, Tr?ger's base and bicalutamide) in the reversed-phase chromatographic mode. By optimizing the chromatographic conditions such as formic acid content, mobile phase composition, pH values and column temperature, 19 analytes were completely separated with high resolution (1.50-4.48), in which the enantiomeric resolution of silymarin, 4-hydroxyflavanone, 2-hydroxyflavanone and flavanone were up to 4.34, 4.48, 3.89 and 3.06 within 35 min, respectively. Compared to the native β-CD chiral stationary phase (CDCSP), HTCDP had superior enantiomer separation and chiral recognition abilities. For example, HTCDP completely separated 5 other common chiral drugs, 2 flavanones and 3 triazole pesticides that CDCSP failed to separate. Unlike CDCSP, which has a small cavity (0.65 nm), the two cavities in HTCDP joined by the aryl connector could synergistically accommodate relatively bulky chiral analytes. Thus, HTCDP may have a broader prospect in enantiomeric separation, analysis and detection. This journal is

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

Enhancing the usefulness of cross dehydrogenative coupling reactions with a removable protecting group

A removable protecting group has been identified that allows the products of widely-used cross dehydrogenative couplings to be synthetically elaborated. The method can be used with enantiopure amines with no loss of enantiomeric excess. The methodology is exemplified by a new synthesis of enantiopure praziquantel, the drug used in the treatment of millions of people suffering from the neglected tropical disease, schistosomiasis.