(S)-Praziquantel

Base Information

• Chemical Name: (S)-Praziquantel
• CAS No.: 57452-97-8
• Molecular Formula: C19H24N2O2
• Molecular Weight: 312.412
• UNII: 88027IXB7M
• Nikkaji Number: J343.006E
• Wikidata: Q27269861
• ChEMBL ID: CHEMBL3264245
• Mol file: 57452-97-8.mol

Synonyms:(S)-Praziquantel;57452-97-8;(S)-(-)-praziquantel;(+)-Praziquantel;Praziquantel, (+)-;(S)-(+)-Praziquantel;UNII-88027IXB7M;88027IXB7M;(11bS)-2-(cyclohexanecarbonyl)-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one;4H-Pyrazino(2,1-a)isoquinolin-4-one, 2-(cyclohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-, (11bS)-;(S)-2-(Cyclohexanecarbonyl)-2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one;(+)-Pragiquantel;PRAZIQUANTEL, (S)-;BIDD:GT0143;SCHEMBL340363;CHEMBL3264245;MFCD22571800;PD132338;I11684;Q27269861

Chemical Property of (S)-Praziquantel

Chemical Property:

• PSA: 40.62000
• LogP: 2.41070
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly, Sonicated), Ethanol (Slightly, Sonicated)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 312.183778013
• Heavy Atom Count: 23
• Complexity: 472

Purity/Quality:

99% ^*data from raw suppliers

(S)-Praziquantel ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C(=O)N2CC3C4=CC=CC=C4CCN3C(=O)C2
• Isomeric SMILES: C1CCC(CC1)C(=O)N2C[C@@H]3C4=CC=CC=C4CCN3C(=O)C2
• 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.

Technology Process of (S)-Praziquantel

There total 12 articles about (S)-Praziquantel which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

(S)-(-)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one (99746-73-3,55375-90-1) + cyclohexanylcarbonyl chloride (2719-27-9) → (+)-Praziquantel (57452-97-8,135526-78-2,57452-31-0,57452-98-9)

Guidance literature:

With sodium carbonate; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2013.11.004

Reference yield: 78.0%

(S)-1-[(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)]cyclohexanecarboxylic acid amide (60567-47-7) + chloroacetyl chloride (79-04-9) → (+)-Praziquantel (57452-97-8,135526-78-2,57452-31-0,57452-98-9)

Guidance literature:

(S)-1-[(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)]cyclohexanecarboxylic acid amide; chloroacetyl chloride; With sodium hydroxide; In dichloromethane; at 20 ℃; for 0.5h;

With benzyltrimethylammonium chloride; In dichloromethane; for 2h; Reflux;

DOI:10.1039/c3ob40503f

Reference yield:

2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one (55268-74-1,135526-78-2,57452-31-0,57452-98-9) → (+)-Praziquantel (57452-97-8,135526-78-2,57452-31-0,57452-98-9) + (-)-Praziquantel (135526-78-2,57452-31-0,57452-98-9)

Guidance literature:

With tetraproline chiral stationary phase packed on HPLC column; In hexane; isopropyl alcohol; Resolution of racemate;

DOI:10.1002/chir.22001

upstream raw materials:

2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one

1-(aminomethyl)-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

1-(R)-(aminomethyl)-2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

1,2,3,4-tetrahydroisoquinoline

Downstream raw materials:

(-)-Praziquantel

2-cyclohexanecarbonyl-1,2,3,6,7,11b-hexahydro-pyrazino[2,1-a]isoquinolin-4-one

Refernces

• 1、 Li, Yuanyuan,Li, Qiang,Zhu, Nan,Gao, Zhuxian,Ma, Yulong. "Cellulose type chiral stationary phase based on reduced graphene oxide@silica gel for the enantiomer separation of chiral compounds". . p. 996 - 1004. Retrieved 2018/07/29.
• 2、 Sharma, Lalit Kumar,Cupit, Pauline M.,Goronga, Tino,Webb, Thomas R.,Cunningham, Charles. "Design and synthesis of molecular probes for the determination of the target of the anthelmintic drug praziquantel". . p. 2469 - 2472. Retrieved 2014/05/20.