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Elucidation of the Active Conformation of Antiproliferative Sulfonamides, 5-Arylsulfonyl-1,5-benzodiazepin-2-ones. | LitMetric
The 5-arylsulfonyl-1,5-benzodiazepin-2-ones with antiproliferative activity were prepared and successfully separated into the (a,a)- and (a,a)-atropisomers with extraordinary stability (Δ = ∼130 kJ/mol) by freezing the conformation around the sp-sp axis in an Ar-N(SO) moiety with a C6-methyl group. Also, by introducing a C3-methyl group (central chirality) into the 1,5-benzodiazepine nucleus, the stereochemistry at the axis was biased to take solely one diastereomer with a relative stereochemistry of (a*,a*,3*). The (a) stereochemistry was crucial for exerting the antiproliferative activity.
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