Diastereoisomers of 2-benzyl-2, 3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol: potential anti-inflammatory agents.
The synthesis and biological activity of the novel diastereoisomers of 2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol is reported. The 2,2-coupled indane dimers were synthesised by coupling of the silyl enol ether of 1-indanone with the dimethyl ketal of 2-indanone. The coupled product was directly alkylated to give the racemic ketone which was reduced to the diastereoisomeric alcohols. The alcohols were separated and their relative stereochemistry was established by X-ray crystallography. These molecules demonstrate significant anti-inflammatory activity in vivo and in vitro and may represent a new class of anti-inflammatory agent.
Sheridan
Helen
H
Trinity College Dublin, School of Pharmacy and Pharmaceutical Sciences, Dublin 2, Ireland. hsheridn@tcd.ie
Walsh
John J
JJ
Cogan
Carina
C
Jordan
Michael
M
McCabe
Tom
T
Passante
Egle
E
Frankish
Neil H
NH
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D018360:Crystallography, X-Ray; D006168:Guinea Pigs; D006632:Histamine / Q000378:metabolism; D007192:Indenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D051379:Mice; D008968:Molecular Conformation; D051381:Rats; D013237:Stereoisomerism; D001619:beta-N-Acetylhexosaminidases / Q000378:metabolism
C546013:2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol; D000893:Anti-Inflammatory Agents; D007192:Indenes; D006632:Histamine; D001619:beta-N-Acetylhexosaminidases