Synthesis, in vitro cytotoxicity and in vivo anti-inflammatory activity of long chain 3-amino-1,2-diols.
The synthesis of long chain 3-amino-1,2-diols was carried out based on Sharpless asymmetric epoxidation of long chain allylic alcohols and regioselective nucleophilic ring opening by azido group. The in vitro cytotoxicity of the compounds prepared was evaluated against six solid tumor cell lines (A2780, H322, LL, WiDr, C26-10, UMSCC-22B). Free 3-amino-1,2-diols exhibited IC50 values between 1.45 microM and 32 microM. These compounds also presented interesting inhibition of carrageenin-induced paw edema in rats (85.3% - 79.6% at a concentration of 0.15 mmol/kg).
Padrón
J M
JM
Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Tenerife, Spain.
Martin
V S
VS
Hadjipavlou-Litina
D
D
Noula
C
C
Constantinou-Kokotou
V
V
Peters
G J
GJ
Kokotos
G
G
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000633:toxicity; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D020128:Inhibitory Concentration 50; D007700:Kinetics; D008956:Models, Chemical; D051381:Rats; D013110:Sphingosine / Q000031:analogs & derivatives*; D014407:Tumor Cells, Cultured
D000605:Amino Alcohols; D000893:Anti-Inflammatory Agents; D013110:Sphingosine