79958-41-1Relevant academic research and scientific papers
Novel insights on saccharin- and acesulfame-based carbonic anhydrase inhibitors: design, synthesis, modelling investigations and biological activity evaluation
Guglielmi, Paolo,Rotondi, Giulia,Secci, Daniela,Angeli, Andrea,Chimenti, Paola,Nocentini, Alessio,Bonardi, Alessandro,Gratteri, Paola,Carradori, Simone,Supuran, Claudiu T.
, p. 1891 - 1905 (2020/10/06)
A large library of saccharin and acesulfame derivatives has been synthesised and evaluated against four isoforms of human carbonic anhydrase, the two off-targets hCA I/II and the tumour related isoforms hCA IX/XII. Different strategies of scaffold modification have been attempted on both saccharin as well as acesulfame core leading to the obtainment of 60 compounds. Some of them exhibited inhibitory activity in the nanomolar range, albeit some of the performed changes led to either micromolar activity or to its absence, against hCA IX/XII. Molecular modelling studies focused the attention on the binding mode of these compounds to the enzyme. The proposed inhibition mechanism is the anchoring to zinc-bound water molecule. Docking studies along with molecular dynamics also underlined the importance of the compounds flexibility (e.g. achieved through the insertion of methylene group) which favoured potent and selective hCA inhibition.
In situ Generation and Utilization of CO: An Efficient Route towards N-Substituted Saccharin via Carbonylative Cyclization of 2-Iodosulfonamides
Chavan, Sujit P.,Adithyaraj,Bhanage, Bhalchandra M.
supporting information, p. 2000 - 2003 (2017/09/13)
The present protocol demonstrates the synthesis of N-substituted saccharines via carbonylative cyclization of 2-iodosulfonamides using a Pd(OAc) 2 /Xantphos catalyst system and phenyl formate as a CO source. A variety of saccharin derivatives is synthesized under milder reaction conditions.
Visible-light promoted catalyst-free imidation of arenes and heteroarenes
Song, Lu,Zhang, Long,Luo, Sanzhong,Cheng, Jin-Pei
, p. 14231 - 14234 (2015/01/09)
We described herein a catalyst-free visible-light photolytic protocol for the imidation of arenes and heteroarenes. N-Bromosaccharin was identified as a viable and chemoselective nitrogen radical precursor that undergoes controllable homolytic cleavage under ambient light irradiation. The reaction can be applied to a number of arenes and heteroarenes with good chemo- and regioselectivity. Mechanistic studies revealed that radical chain termination by electron transfer-proton transfer (ET-PT) is the leading productive pathway for the reaction.
