Synthesis and pharmacological screening of new phenylpiperazinepropane derivatives and their enantiomers.
Enantiomers of phenylpiperazinepropane-1,2-diol derivatives were synthesized with the purpose to obtain a better antitussive activity/sedative effect ratio. (S)-isomers showed better pharmacological profiles than (R)-isomers and corresponding racemates. Among the (S)-isomers, the unsubstituted compound, levodropropizine (S(-)-3-(4-phenyl-piperazin-1-yl)-propane-1,2-diol, DF 526), has the most favourable antitussive activity/sedative effect ratio and was selected for pharmaco-toxicological evaluation.
Giani
R
R
Research & Development Laboratories, Dompé Farmaceutici S.p.A., Milan, Italy.
Marinone
E
E
Melillo
G
G
Borsa
M
M
Tonon
G C
GC
D000818:Animals; D000996:Antitussive Agents / Q000009:adverse effects / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D006168:Guinea Pigs; D007536:Isomerism; D008297:Male; D051379:Mice; D011409:Propylene Glycols / Q000009:adverse effects / Q000138:chemical synthesis*; D012890:Sleep / Q000187:drug effects
D000996:Antitussive Agents; D011409:Propylene Glycols; C035916:dipropizine