Synthesis, structure and properties of N-aminosaccharin – A selective inhibitor of human carbonic anhydrase I. Issue 2 (11th January 2017)

• Record Type: Journal Article
• Authors: Kuznetsov, Mikhail A.; Shestakov, Aleksandr N.; Zibinsky, Mikhail; Krasavin, Mikhail; Supuran, Claudiu T.; Kalinin, Stanislav; Tanç, Muhammet
• Is Part Of: Tetrahedron letters. Volume 58:Issue 2(2017)
• Page Start: 172
• Page End: 174
• Publication Date: 2017-01-11
• Subjects: N-Aminosaccharin -- N-Amination -- hCA I inhibitor -- Oxidative aminoaziridination -- Ligand efficiency; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.12.005
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Previously unknown N -aminosaccharin was prepared. N -Aminosaccharin activity in different reactions has been investigated. N -Aminosaccharin was identified to be a selective low micromolar inhibitor of h CA I. Abstract: Previously unknown N -aminosaccharin was prepared in good yield via the one-step direct amination of saccharin sodium salt with hydroxylamine- O -mesitylenesulfonic acid (MSH) and its reactivity investigated. N -aminosaccharin and its derivatives were tested against h CA isoforms and the parent compound was identified to be a selective, low micromolar inhibitor (Ki = 8.8 μM) of h CA I. These findings provide a ligand-efficient starting point for the design of potent h CA I inhibitors – a promising drug target for retinal/cerebral edema treatment.