Synthesis of some 2-arylpropionic acid amides as prodrugs.
The synthesis of amide prodrugs of some 2-arylpropionic acids (ibuprofen, naproxen, diclofenac and ketorolac) and the enantiomeric separation of these compounds are reported in this paper. The compounds were prepared from the corresponding 2-arylpropionic acids and (R-(-)-2-amino-1-butanol in the presence of N,N'-dicyclohexylcarbodiimide (DCC). Enantiomers were separated by preparative chromatography or crystallisation. The structure were confirmed by infrared, nuclear magnetic resonance and elementary analysis. The compounds prepared in the study have significant analgesic activity.
Akgün
H
H
Hacettepe University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ankara, Turkey.
Tozkoparan
B
B
Ertan
M
M
Aksu
F
F
Inan
S Y
SY
D000287:Administration, Topical; D000577:Amides / Q000009:adverse effects / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000009:adverse effects / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D003460:Crystallization; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D011355:Prodrugs / Q000009:adverse effects / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D011422:Propionates / Q000009:adverse effects / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D012869:Skin Absorption; D013237:Stereoisomerism; D013276:Stomach Ulcer / Q000139:chemically induced
D000577:Amides; D000893:Anti-Inflammatory Agents; D011355:Prodrugs; D011422:Propionates