698350-87-7Relevant academic research and scientific papers
Generic synthesis of β-sultams via domino alkylation of bromomethanesulfonamides
Barton, William R.S.,Paquette, Leo A.
, p. 113 - 119 (2004)
Reaction of N-substituted bromomethanesulfonamides with 2 equiv of potassium carbonate and an α-halo ketone, ester, or nitrile leads directly to 3-substituted β-sultams. The first step is intermolecular and is followed by an intramolecular alkylation. The
Synthesis and use of sulfonamide-, sulfoxide-, or sulfone-containing aminoglycoside-CoA bisubstrates as mechanistic probes for aminoglycoside N-6′-acetyltransferase
Gao, Feng,Yan, Xuxu,Zahr, Omar,Larsen, Aaron,Vong, Kenward,Auclair, Karine
supporting information; experimental part, p. 5518 - 5522 (2009/05/30)
Aminoglycoside-coenzyme A conjugates are challenging synthetic targets because of the wealth of functional groups and high polarity of the starting materials. We previously reported a one-pot synthesis of amide-linked aminoglycoside-CoA bisubstrates. These molecules are nanomolar inhibitors of aminoglycoside N-6′-acetyltransferase Ii (AAC(6′)-Ii), an important enzyme involved in bacterial resistance to aminoglycoside antibiotics. We report here the synthesis and biological activity of five new aminoglycoside-CoA bisubstrates containing sulfonamide, sulfoxide, or sulfone groups. Interestingly, the sulfonamide-linked bisubstrate, which was expected to best mimic the tetrahedral intermediate, does not show improved inhibition when compared with amide-linked bisubstrates. On the other hand, most of the sulfone- and sulfoxide-containing bisubstrates prepared are nanomolar inhibitors of AAC(6′)-Ii.
