Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers.
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.
Franks
Marion A
MA
Department of Chemistry, Wake Forest University, PO Box 7486, Winston-Salem, NC 27109, USA.
Schrader
Edward A
EA
Pietsch
E Christine
EC
Pennella
Daniel R
DR
Torti
Suzy V
SV
Welker
Mark E
ME
D000438:Alcohols / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000818:Animals; D016588:Anticarcinogenic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002244:Carbon / Q000737:chemistry; D045744:Cell Line, Tumor; D002614:Chelating Agents / Q000737:chemistry*; D004583:Electrons; D004790:Enzyme Induction / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000378:metabolism*; D010087:Oxides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013455:Sulfur / Q000737:chemistry*
D000438:Alcohols; D000475:Alkenes; D016588:Anticarcinogenic Agents; D002614:Chelating Agents; D010087:Oxides; D013438:Sulfhydryl Compounds; C502394:oxathiolene oxide; D013455:Sulfur; D002244:Carbon; D016660:NAD(P)H Dehydrogenase (Quinone); C447479:NQO1 protein, human