Abstract
Bioisosteric analogues of pachastrissamine that contain sulfur and selenium atoms replacing the oxygen in the ring system, were efficiently prepared from a cyclic sulfate intermediate by sequential intermolecular and intramolecular S(N)2 displacement reactions of the dianions. The analogues exhibited cytotoxicities comparable to that of pachastrissamine.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Cell Line, Tumor
-
Cell Survival / drug effects
-
Cyclization
-
Humans
-
Molecular Structure
-
Oxygen / chemistry
-
Selenium / chemistry*
-
Sphingosine / analogs & derivatives*
-
Sphingosine / chemical synthesis
-
Sphingosine / pharmacology
-
Sulfates / chemistry*
-
Sulfur / chemistry*
Substances
-
Sulfates
-
pachastrissamine
-
Sulfur
-
Selenium
-
Sphingosine
-
Oxygen