14142-90-6Relevant academic research and scientific papers
A convenient method for chemoselective O-methylation of hydroxypyridines
Adamczyk, Maciej,Johnson, Donald D.,Reddy, Rajarathnam E.
, p. 2985 - 2993 (1999)
ethereal-diazomethane in tert-butanol at -20 °C to rt, afforded the corresponding 3-methoxypyridine derivatives (2a-g) in 54-94% yield.
"Click" assembly of novel dual inhibitors of AChE and MAO-B from pyridoxine derivatives for the treatment of Alzheimer's disease
Gao, Juanjuan,Huang, Saipeng,Jia, Zhao,Luo, Yane,Wan, Kaikai,Wang, Ruijie,Wen, Huiyun,Xue, Weiming
, p. 18 - 25 (2022/03/01)
This study fast synthesizes numerous functionalized pyridoxines using click chemistry and assayed in vitro as inhibitors of the acetylcholinesterase (AChE), butyrylcholinesterase, and two monoamine oxidase (MAO) isoforms, MAO-A and MAO-B. Most of the obtained compounds demonstrate good AChE and selective MAO-B inhibitory activities in the micromolar range, especially one compound, called 4k5, exhibits excellent inhibitory performance against AChE (IC50 = 0.0816 ± 0.075 μM) and MAO-B (IC50 = 0.039 ± 0.003 μM). Finally, a docking study is carried out, demonstrating potential binding orientations and interactions of the compounds in terms of the AChE and MAO-B active sites.
Bifunctional pyridoxal derivatives as efficient bioorthogonal reagents for biomacromolecule modifications
Duan, Yuting,Fei, Jiayue,Li, Wei,Mao, Xianxian,Tian, Hongyan,Wang, Xiaojian,Wang, Yuntao,Zhu, Shiyu,Zou, Juan
supporting information, p. 7601 - 7604 (2020/08/25)
Two types of pyridoxal analogs, azido pyridoxal (PL-N3) and carboxyl pyridoxal (PL-COOH), were developed as novel bifunctional bioorthogonal molecules. These molecules showed fast imine formation with hydrazinyl groups and stable covalent linkages via azido/carboxyl groups, and thus were of great use for site-specific peptide and protein modifications.
Pyridoxine-resveratrol hybrids as novel inhibitors of MAO-B with antioxidant and neuroprotective activities for the treatment of Parkinson's disease
Cao, Zhongcheng,Deng, Yong,Li, Wei,Shi, Yichun,Song, Qing,Yang, Xia,Zhang, Li
, (2020/03/10)
A series of pyridoxine-resveratrol hybrids were designed and synthesized as monoamine oxidase B inhibitors for the treatment of Parkinson's disease. Most of them exhibited potent inhibitory activities on MAO-B with high selectivity. Specifically, compounds 12a, 12g and 12l showed the most excellent inhibition to hMAO-B with the IC50 values of 0.01 μM, 0.01 μM and 0.02 μM, respectively. Further reversibility study demonstrated that 12a and 12l were reversible and 12g was irreversible MAO-B inhibitors. Molecular docking studies of MAO revealed the binding mode and high selectivity of these compounds with MAO-B. In addition, these three representative compounds also exhibited low cytotoxicity and excellent neuroprotective effect in the test on H2O2-induced PC-12 cell injury. Moreover, 12a, 12g and 12l showed good antioxidant activities and high blood-brain barrier permeability. Overall, all of these results highlighted 12a, 12g and 12l were potential and excellent MAO-B inhibitors for PD treatment.
Synthesis and antibacterial activity of novel phosphonium salts on the basis of pyridoxine
Pugachev, Mikhail V.,Shtyrlin, Nikita V.,Sysoeva, Lubov P.,Nikitina, Elena V.,Abdullin, Timur I.,Iksanova, Alfiya G.,Ilaeva, Alina A.,Musin, Rashid Z.,Berdnikov, Eugeny A.,Shtyrlin, Yurii G.
, p. 4388 - 4395 (2013/07/27)
A series of 13 phosphonium salts on the basis of pyridoxine derivatives were synthesized and their antibacterial activity against clinically relevant strains was tested in vitro. All compounds were almost inactive against gram-negative bacteria and exhibited structure-dependent activity against gram-positive bacteria. A crucial role of ketal protection group in phosphonium salts for their antibacterial properties was demonstrated. Among synthesized compounds 5,6-bis[triphenylphosphonio(methyl)]-2,2,8-trimethyl-4H-[1,3] dioxino[4,5-c]pyridine dichloride (compound 20) was found to be the most effective towards Staphylococcus aureus and Staphylococcus epidermidis strains (MIC 5 μg/ml). The mechanism of antibacterial activity of this compound probably involves cell penetration and interaction with genomic and plasmid DNA.
A Convergent Triflate Displacement Approach to (α-Monofluoroalkyl)phosphonates
Berkowitz, David B.,Bose, Mohua,Asher, Nathan G.
, p. 2009 - 2012 (2007/10/03)
(Formula Presented) Treatment of primary alkyl triflates or iodides with the potassium salt of diethyl (α-fluoro-α-phenylsulfonylmethyl)phosphonate yields (α-fluoro-α-phenylsulfonylalkyl)phosphonates. These can be cleanly desulfonated, in a matter of minu
