Chemical synthesis and actions of 11,12-thiirano-hepoxilin A3.
A novel analog of hepoxilin A3 has been chemically synthesized in which the 11,12-epoxide group has been altered to a thiirano group. This has been accomplished through allylic rearrangement of unnatural (11 R, 12 R)-hepoxilin B3 under Mitsunobu conditions, first into unnatural (11 R, 12 R)-hepoxilin A3, followed by conversion of this compound with inversion of the epoxide centers into the thiirano-hepoxilin A3 having the natural 11 S, 12 S configuration. We also report herein evidence showing that thiirano-hepoxilin A3 raises intracellular calcium concentrations in intact human neutrophils.
Demin
P M
PM
Research Institute, The Hospital for Sick Children, Toronto, Canada.
Reynaud
D
D
Pace-Asciak
C R
CR
D015126:8,11,14-Eicosatrienoic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002118:Calcium / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009504:Neutrophils / Q000187:drug effects* / Q000378:metabolism
C102876:11,12-thiiranohepoxilin A3; D015126:8,11,14-Eicosatrienoic Acid; D002118:Calcium