15449-00-0Relevant articles and documents
Copper-catalyzed arenes amination with saccharins
Sun, Kai,Li, Yan,Zhang, Qian
, p. 1354 - 1358 (2015)
A novel copper-catalyzed direct C-N formation reaction of simple arenes with cheap and pharmacological saccharin derivatives under relatively mild conditions was developed with arenes as limiting reagents. This work provided a new method for oxidative cou
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.
Efficient copper-catalyzed N-arylation of NH-containing heterocycles and sulfonamides with arenediazonium tetrafluoroborates
Ouyang, Yu-Qing,Yang, Zhen-Hua,Chen, Zhong-Hui,Zhao, Sheng-Yin
, p. 771 - 778 (2017/04/06)
A practical copper-catalyzed N-arylation of NH-containing heterocycles with arenediazonium tetrafluoroborates has been developed using CuCl as catalyst and K2CO3 as additive under ligand-free conditions. This reaction system has wide substrate scope including imides, 1H-pyrazole, 1H-tetrazoles, 1,2-benzisothiazol-3(2H)-one, and related sulfonamides and gives moderate to excellent yields (up to 95%) of the desired products. This strategy is very general, simple, environmentally friendly, and tolerant of oxygen.
Preparation method of 2-phenyl-1,1-dioxo-1,2-benzisothiazole-3(2H)-one
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Paragraph 0023; 0049; 0050, (2017/01/12)
The invention relates to a preparation method of 2-phenyl-1,1-dioxo-1,2-benzisothiazole-3(2H)-one. The preparation method comprises the following steps: (1) mixing aniline, water and a fluoboric acid aqueous solution, then dropwise adding a sodium nitrite aqueous solution while stirring at the temperature of 0-5 DEG C, heating to room temperature after dropwise adding is finished, continuing stirring and reacting for 1-2 hours, and carrying out suction filtration to obtain benzenediazonium tetrafluoroborate; (2) stirring and mixing 1,1-dioxo-1,2-benzisothiazole-3(2H)-one, alkali, a copper salt catalyst and a solvent at the temperature from minus 5 DEG C to 5 DEG C, then adding the benzenediazonium tetrafluoroborate in batches, reacting for 6-8 hours while stirring at the temperature from minus 5 DEG C to room temperature, and after reaction is finished, extracting, drying, removing the solvent by evaporation, and carrying out recrystallization to obtain the final product. The copper salt is used as the catalyst, so that reaction time is shortened, and meanwhile, yield is improved; the starting material of the preparation method is easy to obtain, the cost is low, reaction operation is simple, a reaction path is short, industrial production is facilitated, and the application prospect is good.
