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Synthesis and Properties of cis ‐ and trans ‐4‐Hydroxypraziquantel
Author(s) -
KiecKoowicz Katarzyna,
Farghaly Zinab S.,
Blaschke Gottfried
Publication year - 1991
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19913240409
Subject(s) - chemistry , ketone , enantiomer , metabolite , anthelmintic , carboxylic acid , racemization , stereochemistry , organic chemistry , ecology , biochemistry , biology
The title compound is the main metabolite of the anthelmintic agent praziquantel. The synthesis or cis ‐ and trans ‐4‐OH derivatives (as well as their enantiomers) of praziquantel is described. Thus, racemic, (+)‐ and (‐)‐pyrazinoisoquinolin‐4‐one ( 1 ) was reacted either with 4‐oxocyclohexane carboxylic acid chloride or with 4‐oxocyclohexane carboxylic acid in the presence of DCC to give the racemic, (+)‐ and (‐)‐ketone 2 . Racemic, (+)‐ and (‐)‐ketone 2 , respectively, was reduced with K‐Selectride yielding the racemic, (+)‐ and (‐)‐ cis ‐4‐OH derivatives 3a . or with NaBH 4 producing racemic, (+)‐and (‐)‐ trans ‐4‐OH derivatives 3b . The physicochemical properties (MS, NMR, HPLC) of both isomers and their enantiomers are reported.