33264-82-3Relevant articles and documents
Synthesis, structural characterization, docking, lipophilicity and cytotoxicity of 1-[(1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]-3-alkyl carbamates, novel acetylcholinesterase and butyrylcholinesterase pseudo-irreversible inhibitors
Pejchal, Vladimír,?těpánková, ?árka,Pejchalová, Marcela,Královec, Karel,Havelek, Radim,R??i?ková, Zdenka,Ajani, Haresh,Lo, Rabindranath,Lep?ík, Martin
, p. 1560 - 1572 (2016)
In the current study, sixteen novel derivatives of (R)-1-(6-fluorobenzo[d]thiazol-2-yl)ethanamine were synthesized as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors. Chemical structures together with purity of the synthesized compounds were substantiated by IR, 1H, 13C, 19F NMR, high resolution mass spectrometry and elemental analysis. The optical activities were confirmed by optical rotation measurements. The synthesized compounds were evaluated for their AChE and BChE inhibitory activities. In addition, the cytotoxicity of the most active compounds was investigated against human cell lines employing XTT tetrazolium salt reduction assay and xCELLigence system allowing a label-free assessment of the cells proliferation. Our results demonstrated that the inhibitory mechanism was confirmed to be pseudo-irreversible, in line with previous studies on carbamates. Compounds indicated as 3b, 3d, 3l and 3n showed the best AChE inhibitory activity of all the evaluated compounds and were up to tenfold more potent than standard drug rivastigmine. The binding mode was determined using state-of-the-art covalent docking and scoring methodology. The obtained data clearly demonstrated that 3b, 3d, 3l and 3n benzothiazole carbamates possess high inhibitory activity against AChE and BChE and concurrently negligible cytotoxicity. In conclusion, our results indicate, that these derivatives could be promising in an effective therapeutic intervention for Alzheimer's disease.
AcOH-mediated aerobic oxidative synthesis of 2-thioalkylbenzothiazoles via a three-component reaction
Li, Xiaowei,Li, Yuxiu,Liu, Ruihua,Wang, Zemin,Li, Xiangqian,Shi, Dayong
supporting information, (2020/05/28)
An AcOH-mediated three-component reaction of 2-aminothiophenols, α,β-unsaturated aldehydes, and thiophenols to prepare the high value-added 2-thioalkylbenzothiazoles was developed. The reaction was conducted under metal-free conditions, where oxygen served as the terminal oxidant. In addition, this strategy is tolerant of kinds of functional groups, providing efficient access to a variety of functionalized benzothiazole derivatives in moderate to good yields. What's more, this reaction has complete regioslectivity and provides a powerful method for building complex molecules.
Synthesis, structural characterization, antimicrobial and antifungal activity of substituted 6-fluorobenzo[d]thiazole amides
Pejchal, Vladimír,Pejchalová, Marcela,R??i?ková, Zdeňka
, p. 3660 - 3670 (2015/09/07)
A series of novel 1-[(1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]-3-substituted phenyl amides was synthesized by the condensation reaction of (1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethanamine with substituted benzoyl chlorides under mild conditions. Their structures were confirmed by 1H NMR, 13C NMR and 19F NMR spectra, elemental analyses and in three cases also by single-crystal X-ray diffraction techniques. The optical activities were confirmed by optical rotation measurements. All the synthesized compounds were screened for antibacterial and antifungal activity against a variety of bacterial and fungal strains. Some of the compounds reveal antibacterial and antifungal activity comparable or slightly better to that of chloramphenicol, cefoperazone and amphotericin B used as medicinal standards.
