57452-98-9

Basic information

• Product Name: l-Praziquantel
• Synonyms: (R)-(-)-Praziquantel;4H-Pyrazino[2,1-a]isoquinolin-4-one, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-, (11bR)- (9CI);4H-Pyrazino[2,1-a]isoquinolin-4-one, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-, (R)-;l-Praziquantel;(-)-Pragiquantel;(R)-(-)-Praziquantel,(11bR)-2-(cyclohexanecarbonyl)-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one;(11bR)-2-(Cyclohexylcarbonyl)-1,2,3,6,7,11B-Hexahydro-4H-Pyrazino[2,1-a]Isoquinolin-4-One;Lopac-P-4668
• CAS NO: 57452-98-9
• Molecular Formula: C19H24N2O2
• Molecular Weight: 312.40606
• Product Categories: api
• Mol File: 57452-98-9.mol
• Article Data: 52

Chemical Properties

• Melting Point: 113-115 °C
• Boiling Point: 544.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.22±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: -0.98±0.20(Predicted)
• CAS DataBase Reference: l-Praziquantel(CAS DataBase Reference)
• NIST Chemistry Reference: l-Praziquantel(57452-98-9)
• EPA Substance Registry System: l-Praziquantel(57452-98-9)

Safety Data

• Hazardous Substances Data: 57452-98-9(Hazardous Substances Data)

Usage

Description

l-Praziquantel is a pharmaceutical compound that is the active enantiomer of praziquantel, specifically effective against juvenile Schistosoma mansoni infestations in mice. It has demonstrated the ability to inhibit Schistosoma mansoni infestation both in vitro and in vivo, making it a valuable agent in the treatment of parasitic infections.

Uses

Used in Pharmaceutical Industry:
l-Praziquantel is used as an antiparasitic agent for the treatment of Schistosoma mansoni infestations. It is particularly effective against juvenile stages of the parasite, providing a targeted approach to combat the infection in both in vitro and in vivo settings. This application is crucial in the development of treatments for schistosomiasis, a disease caused by parasitic flatworms of the genus Schistosoma.

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-/m0/s1

Upstream product

• 13156-95-1 2-chloro-N-phenethylacetamide 
• 210223-97-5 2-[(2,2-dimethoxyethyl)amino]-N-(2-phenylethyl)acetamide hydrochloride 
• 64-04-0 phenethylamine 
• 106148-28-1 4-benzyl-6-hydroxy-1-phenethylpiperazin-2-one 
• 105279-85-4 2-benzyl-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 93255-06-2 Cyclohexanecarboxylic acid bicyclo[4.2.0]octa-1,3,5-trien-7-ylmethyl-carbamoylmethyl-amide 
• 55375-91-2 (-)-2-Benzoyl-4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline 
• 61196-40-5 2-acetyl-2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one 
• 87693-78-5 4-benzoyl-2,6-dioxo-1-phenethyl piperazine 
• 87693-80-9 1-(2-phenylethyl)-4-benzoyl-2-hydroxypiperazin-6-one 
• 87693-77-4 4-acetyl-2,6-dioxo-1-phenethyl piperazine 
• 87693-72-9 4-(cyclohexylcarbonyl)-2,6-di-hydroxyiminopiperazine 
• 87693-79-6 1-(2-phenyl)ethyl-4-acetyl-2-hydroxypiperazine-6-one 
• 87693-73-0 4-(cyclohexylcarbonyl)-2,6-dioxopiperazine 

Downstream Products

• 1609979-51-2 C₂₃H₂₃N₃O₂ 
• 1609979-52-3 C₃₄H₄₀N₆O₄ 
• 99746-73-3 (S)-(-)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 55375-92-3 (R)-(-)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one 
• 135526-78-2 (-)-Praziquantel 
• 57452-97-8 (+)-Praziquantel 
• 1609986-43-7 C₁₉H₁₇N₃O₄ 
• 1609986-44-8 C₁₉H₁₉N₃O₂ 
• 1609979-49-8 C₂₈H₂₂F₃N₅O₃ 
• 1609979-50-1 C₃₁H₂₄F₃N₅O₃ 
• 135526-78-2 praziquantel 
• 135526-78-2 praziquantel 
• 134924-71-3 2-(4-trans-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 
• 134924-68-8 2-(4-cis-hydroxycyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino<2,1-a>isoquinolin-4-one 

Relevant articles and documents

Preparation method of praziquantel

The invention relates to the technical field of medical intermediates, and provides a praziquantel preparation method which comprises the following steps: S1, adding isoquinoline, cyanide, tetrabutylammonium bromide and dichloroethane into a reactor, and dropwise adding benzoyl chloride for reaction to obtain a first-step product; s2, performing catalytic hydrogenation on the first-step product to obtain a second-step product; and S3, adding ethyl acetate into the second-step product, stirring and dissolving, adding sodium bicarbonate, dropwise adding chloroacetyl chloride, stirring and reacting to obtain a praziquantel crude product, and recrystallizing to obtain praziquantel. Through the technical scheme, the problems of long reaction process, high energy consumption and low yield in the prior art are solved.

Two approaches for the synthesis of levo-praziquantel

We report herein the development of two pathways for the preparation of levo-praziquantel (R-PZQ), which involves three-/four-step processes of a mechanochemical (asymmetric) aza-Henry/acylation reaction, a hydrogenation reaction, (chiral resolution) and a solvent-free acylation-ring closing reaction. The key intermediate (R)-1-aminomethyl tetrahydroisoquinoline could be obtained either by chiral resolution with a rational reuse of the S-isomer or by mechanochemical enantioselective synthesis that refrained from using a bulky toxic solvent. The efficiency and scalability of both the developed routes were demonstrated and desired target product was obtained in a satisfactory yield with excellent enantiopurity (>99%), offering practical, concise and environmentally friendly alternatives to access R-PZQ.

Preparation method of (R)-praziquantel

The invention provides a preparation method of (R)-praziquantel. The method for preparing (R)-praziquantel comprises the following steps: by taking dihydroisoquinoline and nitromethane as raw materials, carrying out solvent-free Henry reaction and nickel catalytic hydrogenation reduction reaction under mechanical ball milling to obtain a 1-aminomethyl-2-chloracetyl tetrahydroisoquinoline intermediate; carrying out salifying resolution reaction on the intermediate and an acidic resolving agent to obtain a (R)-praziquantel intermediate; and carrying out solvent-free amidation-cyclization reaction on the (R)-praziquantel intermediate and cyclohexanecarboxylic acid under mechanical ball milling to synthesize the (R)-praziquantel. According to the method, mother liquor left after crystallization and resolution can be subjected to racemization recovery and reutilization, so that the yield of the (R)-praziquantel intermediate is greatly increased; the method is easy and convenient to operate,mild in reaction condition and environmentally friendly, and the obtained (R)-praziquantel product is high in optical purity and has good application and popularization prospects.