106590-58-3Relevant academic research and scientific papers
A Practical and High-Affinity Fluorescent Probe for Butyrylcholinesterase: A Good Strategy for Binding Affinity Characterization
Chen, Yao,Du, Chenxi,Hu, Yanyu,Li, Yueqing,Liu, Hui,Lu, Xin,Qiu, Weimin,Sun, Haopeng,Sun, Tianyu,Wang, Lei
, (2022/03/15)
Butyrylcholinesterase (BChE) is regarded as a promising target for the treatment of Alzheimer's disease (AD), as its level significantly increases along with the progress of this disease. Therefore, the development of potent and high-affinity small-molecule BChE inhibitors may be a new strategy for the discovery of anti-AD drugs. However, the current Ellman's method is unable to evaluate the affinity of compounds with BChE, and has a few deficiencies in drug development. Herein, the first small-molecule fluorescence polarization (FP) probes for BChE were rationally designed based on a high affinity inhibitor. Studies indicated that probe F6 exhibited satisfactory fluorescence intensity and suitable fluorescent properties that were compatible with the filters in the FP system. Meanwhile, probe F6 exhibited potent binding affinity to BChE. It is feasible to be applied in detecting the affinity of non-fluorescent compounds to BChE, which lays a solid foundation for the development of small-molecule BChE inhibitors. At the same time, it also can be applied as a valuable chemical tool for better understanding the molecular biological mechanism of BChE.
Azodicarboxylate-free esterification with triphenylphosphine mediated by flavin and visible light: method development and stereoselectivity control
M?rz, Michal,Kohout, Michal,Nevesely, Tomá?,Chudoba, Josef,Pruka?a, Dorota,Niziński, Stanislaw,Sikorski, Marek,Burdziński, Gotard,Cibulka, Radek
supporting information, p. 6809 - 6817 (2018/09/29)
Triphenylphosphine (Ph3P) activated by various electrophiles (e.g., alkyl diazocarboxylates) represents an effective mediator of esterification and other nucleophilic substitution reactions. We report herein an aza-reagent-free procedure using flavin catalyst (3-methyl riboflavin tetraacetate), triphenylphosphine, and visible light (448 nm), which allows effective esterification of aromatic and aliphatic carboxylic acids with alcohols. Mechanistic study confirmed that photoinduced electron transfer from triphenylphosphine to excited flavin with the formation of Ph3P+ is a crucial step in the catalytic cycle. This allows reactive alkoxyphosphonium species to be generated by reaction of an alcohol with Ph3P+ followed by single-electron oxidation. Unexpected stereoselectivity control by the solvent was observed, allowing switching from inversion to retention of configuration during esterification of (S)- or (R)-1-phenylethanol; for example with phenylacetic acid, the ratio shifting from 10?:?90 (retention?:?inversion) in trifluoromethylbenzene to 99.9?:?0.1 in acetonitrile. Our method uses nitrobenzene to regenerate the flavin photocatalyst. This new approach to flavin re-oxidation has also been successfully proved in benzyl alcohol oxidation, which is a “standard” process among flavin-mediated photooxidations.
Synthesis of a Distamycin Analogue: Tris(m-benzamido) Compound
Rajagopalan, Malini,Rao, K. Ekambareswara,Ayyer, Jayalekshmy,Sasisekharan, V.
, p. 1021 - 1024 (2007/10/02)
In order to understand the role of curvature of ligand in conformational and chemical specificity of DNA-drug interactions a number of compounds have been synthesised.The synthetic strategy for one of the compounds in the series, tris(m-benzamido) compound, an analogue of Dst, which is essentially based on the route used by Bialer et al. , 2239> for the synthesis of Dst with some modifications wherever necessary is reported.
