166521-76-2Relevant articles and documents
Mild and recyclable catalytic oxidation of pyridines to N-oxides with H2O2 in water mediated by a vanadium-substituted polyoxometalate
Ding, Yong,Zhao, Wei,Song, Wenfeng,Zhang, Zhenxin,Ma, Baochun
, p. 1486 - 1489 (2011)
A vanadium-substituted polyoxometalate, K6[PW9V 3O40]·4H2O, was used as a recyclable and effective catalyst for the oxidation of pyridines. The reactions were successfully conducted in water under mild conditions. The catalyst could be easily recovered and reused.
Methyl Scanning and Revised Binding Mode of 2-Pralidoxime, an Antidote for Nerve Agent Poisoning
Gambino, Adriana,Burnett, James C.,Koide, Kazunori
supporting information, p. 1893 - 1898 (2020/02/06)
Organophosphorus nerve agents (OPNAs) inhibit acetylcholinesterase (AChE) and, despite the Chemical Weapons Convention arms control treaty, continue to represent a threat to both military personnel and civilians. 2-Pralidoxime (2-PAM) is currently the only therapeutic countermeasure approved by the United States Food and Drug Administration for treating OPNA poisoning. However, 2-PAM is not centrally active due to its hydrophilicity and resulting poor blood-brain barrier permeability; hence, these deficiencies warrant the development of more hydrophobic analogs. Specifically, gaps exist in previously published structure activity relationship (SAR) studies for 2-PAM, thereby making it difficult to rationally design novel analogs that are concomitantly more permeable and more efficacious. In this study, we methodically performed a methyl scan on the core pyridinium of 2-PAM to identify ring positions that could tolerate both additional steric bulk and hydrophobicity. Subsequently, SAR-guided molecular docking was used to rationalize hydropathically feasible binding modes for 2-PAM and the reported derivatives. Overall, the data presented herein provide new insights that may facilitate the rational design of more efficacious 2-PAM analogs.
Synthesis and green metric evaluation of 2-(chloromethyl)-3-methyl-4-(methylsulfonyl)pyridine
Gilbile, Rohidas,Bhavani, Ram,Vyas, Ritu
, p. 930 - 936 (2017/05/29)
2-[[(2-pyridinyl) methyl] sulfinyl]-1H-benzimidazoles are the prominent motif's that belong to the class of prazoles. These are used in the treatment of gastroesophageal reflux disease (GERD) ulcers and other gastric acid related diseases. The present article describes the modified synthesis of 2-chloromethyl-4-methanesulfonyl-3-methyl pyridine (an intermediate utilized in the synthesis of Dexlansoprazole). The advantages of this modification involves (i) N-oxidation of 2,3-lutidine with catalytic quantity of RuCl3 in presence of oxygen (ii) One pot synthesis of 2,3-dimethyl-4-(methylthio) pyridine-N-oxide using 30% NaSH, methyl iodide and tetra butyl ammonium hydroxide (iii) Oxidation of methythio pyridine-N-oxide with 30% H2O2 followed by N-deoxygenation with RuCl3.H2O to produce 2,3-dimethyl-4-(methylsulfonyl)pyridine (iv) Chlorination of the penultimate step using trichloroisocyanuric acid to obtain the desired 2-chloromethyl-4-methanesulfonyl-3-methyl pyridine. Furthermore, green metrics assessment was calculated for the above modified scheme based on the parameters viz., atom economy (AE), reaction mass efficiency (RME) and E-factor. It was observed that, in case of step 4 (oxidation of thiomethyl pyridine-N-oxide), the E-factor value is very less 3.2 which is indicative of less waste generation, when compared to the various steps that are involved in the synthesis.
