Syntheses and biological activities of sulfoximine-based acyclic triaryl olefins.
Sulfoximine-based acyclic triaryl olefins 8 and 9 have been prepared and initial studies have been performed to determine their biological profiles. In contrast to their sulfonyl-substituted analog 2 sulfoximines 8 and 9 show low COX inhibitory activity. All compounds affect the estrogen receptors. While sulfone 2 interacts exclusively with ER β, sulfoximines 8 and 9 reveal almost equal blocking potencies for both estrogen receptors, ER α and ER β. In the tested series, triaryl olefin 9a shows the highest inhibitory activities with 91% and 80%, respectively (at 10 μM).
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056 Aachen, Germany.
Xiao Yun
XY
Chen
Seong Jun
SJ
Park
Helmut
H
Buschmann
Maria
M
De Rosa
Carsten
C
Bolm
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051545:Cyclooxygenase 1 / Q000737:chemistry / Q000378:metabolism; D051546:Cyclooxygenase 2 / Q000737:chemistry / Q000378:metabolism; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D047628:Estrogen Receptor alpha / Q000037:antagonists & inhibitors / Q000378:metabolism; D047629:Estrogen Receptor beta / Q000037:antagonists & inhibitors / Q000378:metabolism; D006801:Humans; D007097:Imines / Q000737:chemistry*; D011485:Protein Binding / Q000187:drug effects; D013450:Sulfones / Q000737:chemistry
D000475:Alkenes; D000894:Anti-Inflammatory Agents, Non-Steroidal; D016861:Cyclooxygenase Inhibitors; D047628:Estrogen Receptor alpha; D047629:Estrogen Receptor beta; D007097:Imines; D013450:Sulfones; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2