Abstract
A number of alkynols have been prepared by Sonogashira coupling of propargyl alcohol to aromatic halides. Chelation-controlled addition of organometallic nucleophiles to these alkynols was then effected followed by the addition of the sulfur electrophiles, sulfur dioxide or thionyl chloride. This methodology was used to prepare a number of oxathiolene oxides, which have been screened as NQO1 (quinone oxidoreductase) inducers.
Publication types
-
Research Support, N.I.H., Extramural
-
Research Support, U.S. Gov't, Non-P.H.S.
-
Research Support, U.S. Gov't, P.H.S.
MeSH terms
-
Alcohols / chemistry
-
Alkenes / chemistry
-
Animals
-
Anticarcinogenic Agents / chemical synthesis*
-
Anticarcinogenic Agents / chemistry
-
Anticarcinogenic Agents / pharmacology*
-
Carbon / chemistry
-
Cell Line, Tumor
-
Chelating Agents / chemistry*
-
Electrons
-
Enzyme Induction / drug effects
-
Mice
-
Molecular Structure
-
NAD(P)H Dehydrogenase (Quinone) / metabolism*
-
Oxides / chemical synthesis*
-
Oxides / chemistry
-
Oxides / pharmacology*
-
Structure-Activity Relationship
-
Sulfhydryl Compounds / chemical synthesis*
-
Sulfhydryl Compounds / chemistry
-
Sulfhydryl Compounds / pharmacology*
-
Sulfur / chemistry*
Substances
-
Alcohols
-
Alkenes
-
Anticarcinogenic Agents
-
Chelating Agents
-
Oxides
-
Sulfhydryl Compounds
-
oxathiolene oxide
-
Sulfur
-
Carbon
-
NAD(P)H Dehydrogenase (Quinone)
-
NQO1 protein, human