54306-35-3Relevant academic research and scientific papers
Identification of N-phenyl-2-(phenylsulfonyl)acetamides/propanamides as new SLC-0111 analogues: Synthesis and evaluation of the carbonic anhydrase inhibitory activities
Elbadawi, Mostafa M.,Eldehna, Wagdy M.,Nocentini, Alessio,Abo-Ashour, Mahmoud F.,Elkaeed, Eslam B.,Abdelgawad, Mohamed A.,Alharbi, Khalid S.,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.,Gratteri, Paola,Al-Sanea, Mohammad M.
, (2021/03/30)
As a front-runner selective CA IX inhibitor currently in Phase Ib/II clinical trials, SLC-0111 has been herein exploited as a lead molecule for development of new different sets of N-phenyl-2-(phenylsulfonyl)acetamides/propanamides incorporating different functionalities; primary sulfonamide (5a-f), free carboxylic (8a, 8d), ethyl ester (8b, 8e), acetyl (8c, 8f) and nitro (10a, 10b), as potential carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. All the prepared analogues have been examined for their CA inhibitory activities towards four human (h) isoenzymes, hCA I, II, IX and XII. Interestingly, replacement of SLC-0111 ureido linker with the flexible sulfonyl acetamide linker, as well as linker branching and elongation strategies successfully enhanced the inhibitory action toward hCA IX isoform, such as in sulfones 5a-d and 5f which displayed better activity than SLC-0111. Furthermore, sulfonamide-based sulfone (5f) and carboxylic acid-based sulfones (8a and 8d) demonstrated interesting selectivity toward the tumor-related hCA IX isoform over both hCA I and hCA II, which suggests them as promising candidates for further development as potential anticancer candidates. Thereafter, the anti-proliferative action for sulfones 5f, 8a and 8d was examined against breast (MCF-7) and colon (HCT-116) cancer cell lines. Also, sulfone 5f was further assessed for its impact on the cell cycle progression and apoptosis in HCT-116 cells.
α-Phenylsulfonyl-N-arylacetamides (α-phenylsulfonylacetanilides): 1H, 13C and 15N NMR spectral characterization
Kolehmainen, Erkki,Janota, Henryk,Gawinecki, Ryszard,Laihia, Katri,Kauppinen, Reijo
, p. 384 - 385 (2007/10/03)
1H and 13C NMR chemical shift assignments for 11 α-phenylsulfonylacetanilides and 15N NMR chemical shifts for four representative congeners are reported. The 1H and 13C chemical shift assignments are based on DQF COSY and PFG 1H, 13C HMQC/HMBC experiments. The 15N NMR chemical shifts were determined by PFG 1H, 15N HMBC experiments. The correlation analyses with Hammett-type substituent constants gave a significant result with δ(C-1) in the aniline ring. Copyright
