- Protocol for Stereoselective Construction of Highly Functionalized Dienyl Sulfonyl Fluoride Warheads
-
A pyrrolidine-mediated Knoevenagel-type reaction for highly stereoselective construction of novel α-halo-1,3-dienylsulfonyl fluorides was achieved in up to 100% Z-selectivity and high yields at room temperature from condensation of the readily available aldehydes and halomethanesulfonyl fluorides. This protocol provided a class of unique α-halo-1,3-dienylsulfonyl fluorides with wide scope and excellent functional group compatibility. The α-halo-1,3-dienylsulfonyl fluorides were used as versatile building blocks in sulfur fluoride exchange click chemistry, Suzuki reaction, and Sonogashira reaction for the assembly of highly functionalized dienyl sulfonyl fluoride derivatives to be applied as covalent warheads for the discovery of new drugs.
- Zhang, Zai-Wei,Wang, Shi-Meng,Fang, Wan-Yin,Lekkala, Ravindar,Qin, Hua-Li
-
p. 13721 - 13734
(2020/12/15)
-
- Synthesis and use of sulfonamide-, sulfoxide-, or sulfone-containing aminoglycoside-CoA bisubstrates as mechanistic probes for aminoglycoside N-6′-acetyltransferase
-
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.
- Gao, Feng,Yan, Xuxu,Zahr, Omar,Larsen, Aaron,Vong, Kenward,Auclair, Karine
-
supporting information; experimental part
p. 5518 - 5522
(2009/05/30)
-
- α-Haloalkanesulfonyl Bromides in Organic Synthesis. 3. α-Alkylidene Ketones and 1,3-Oxathiole 3,3-Dioxides from Trimethylsilyl Enol Ethers
-
α-Alkylidene ketones and 1,3-oxathiole 3,3-dioxides can be conveniently prepared by treatment of trimethylsilyl enol ethers with α-haloalkanesulfonyl bromides followed by an amine base such as 1,5-diazabicyclonon-5-ene (DBN).
- Block, Eric,Aslam, Mohammad,Iyer, Rajeshwari,Hutchinson, John
-
p. 3664 - 3666
(2007/10/02)
-