4377-33-7Relevant articles and documents
Design and synthesis of a cyclitol-derived scaffold with axial pyridyl appendages and its encapsulation of the silver(I) cation
Leo, Pierre-Marc,Morin, Christophe,Philouze, Christian
, p. 1022 - 1024 (2010)
Conversion of a myo-inositol derivative into a scyllo-inositol-derived scaffold with C3ν symmetry bearing three axial pyridyl appendages is presented. This pre-organized hexadentate ligand allows complexation of silver(I). The crystal structure of the complex was established.
2-(N-Methylbenzyl)pyridine: A Potential Liquid Organic Hydrogen Carrier with Fast H2 Release and Stable Activity in Consecutive Cycles
Oh, Jinho,Jeong, Kwanyong,Kim, Tae Wan,Kwon, Hyunguk,Han, Jeong Woo,Park, Ji Hoon,Suh, Young-Woong
, p. 661 - 665 (2018)
The liquid organic hydrogen carrier (LOHC) 2-(N-methylbenzyl)pyridine (MBP) shows good potential for H2 storage based on reversible hydrogenation and dehydrogenation, with an H2 storage density of 6.15 wt %. This material and the corresponding perhydro product (H12-MBP) are liquids at room temperature. Remarkably, H2 release is much faster from H12-MBP over Pd/C than from the benchmark perhydro benzyltoluene over Pt/C at lower temperatures than 270 °C, owing to the addition of N atom into the benzene ring. Since this positive effect is unfavorable to the hydrogenation reaction, more Ru/Al2O3 catalyst or prolonged reaction time must be applied for complete H2 storage. Experiments with repeated hydrogenation–dehydrogenation cycles reveal that reversible H2 storage and release are possible without degradation of the MBP/H12-MBP pair. The prepared MBP satisfies the requirements for chemical stability, handling properties, and cytotoxicity testing.
Rapid and Effective Reaction of 2-Methylpyridin-N-oxides with Triphosgene via a [3,3]-Sigmatropic Rearrangement: Mechanism and Applications
Li, Hao,Nie, Fang-Yuan,Song, Qin-Hua,Xia, Hong-Cheng
, p. 8308 - 8318 (2021/06/28)
A facile and effective synthesis of 2-chloromethylpyridines was developed by a one-pot reaction of 2-alkylpyridin-N-oxides and triphosgene at room temperature. As starting materials, N-oxides of 2-alkylpyridine derivatives, including 2-alkylpyridines, 2-methyl quinolines, and phenanthroline, can react rapidly with triphosgene in the presence of triethylamine, affording 2-chloromethylpyridines in good to excellent yields (52-95%). Using the 2-methylquinoline substrate for the mechanistic study, it has been well demonstrated that the chlorination reaction undergoes a [3,3]-sigmatropic rearrangement, which can be observed as a reversible process by monitoring the intermediates. Moreover, the chlorination reaction can be used to construct a rapid and sensitive fluorescent probe for the detection of phosgene.
Synthesis of 1,2,3-triazole derivatives of hydnocarpic acid isolated from carpotroche brasiliensis seed oil and evaluation of antiproliferative activity
De Sousa, Bianca L.,Demuner, Antonio J.,Dos Santos, Marcelo H.,Ferraz, Guilherme O.,Ferreira-Silva, Guilherme A.,Ionta, Marisa,Osorio, Liseth S.,Pilau, Eduardo J.,Silva, Evandro,Vareja?, Eduardo V. V.
, p. 2500 - 2510 (2020/11/18)
Carpotroche brasiliensis is a tree native to Brazil, belonging to the family Flacurtiaceae, whose seeds contain a group of cyclopentenyl fatty acids: Gorlic (12%), chaulmugric (27%), and hydnocarpic (48.7%). These compounds are considered the main therapeutic agents in the treatment of leprosy. In the present study, a series of novel triazole compounds were obtained by conjugation between hydnocarpic acid and functionalized azides via copper(I)-catalyzed azidealkyne cycloaddition reaction (CuAAC). Hydnocarpic acid and its derivatives were tested against estrogen-positive breast carcinoma (MCF-7), hepatocellular carcinoma (HepG2), and non-small cell lung cancer (A549) cell lines. The (R)-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl-11-(cyclopent-2-en-1-yl)undecanoate (8) displayed promising antiproliferative activity against A549 cells. We demonstrated that this compound selectively inhibited the viability of A549 cell cultures. Furthermore, compound 8 inhibited the clonogenic capacity of A549 cells, and this effect was associated to its ability to inhibit cell cycle progression at G1 phase. These findings indicate that 8 is a promising antitumor agent on A549 cells and support further studies to evaluate the molecular mechanisms underlying its antiproliferative activity. In addition, hydnocarpic acid should be considered as a promising chemical prototype to obtain novel antineoplastic agents.
