Journal
BIOORGANIC CHEMISTRY
Volume 76, Issue -, Pages 140-146Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.bioorg.2017.11.014
Keywords
Primary sulfonamide; Electron-withdrawing group; Nucleophilic aromatic substitution; SMILES rearrangement; Reactivity-matched substrates; Carbonic anhydrase inhibitors; Isoform-selectivity
Funding
- Russian Scientific Fund [14-50-00069]
- Russian Science Foundation [14-50-00069] Funding Source: Russian Science Foundation
Ask authors/readers for more resources
4-Chloro-3-nitrobenzenesulfonamide reacted cleanly at room-temperature with a range of bis-electrophilic phenols bearing an NH-acidic functionality (secondary carboxamide or pyrazole) in the ortho-position. This produced a novel class of [1,4]oxazepine-based primary sulfonamides which exhibited strong inhibition of therapeutically relevant human carbonic anhydrases. 2-Chloronitrobenzene did not enter a similar cyclocondensation process, even under prolonged heating. Thus, the primary sulfonamide functionality plays a dual role by enabling the [1,4]oxazepine ring construction and acting as a enzyme prosthetic zinc-binding group when the resulting [1,4]oxazepine sulfonamides are employed as carbonic anhydrase inhibitors. (C) 2017 Elsevier Inc. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available