31618-90-3Relevant articles and documents
Monosubstituted pillar[5]arene functionalized with (amino)phosphonate fragments are "smart" building blocks for constructing nanosized structures with some s-and p-metal cations in the organic phase
Nazarova, Anastasia A.,Yakimova, Luidmila S.,Padnya, Pavel L.,Evtugyn, Vladimir G.,Osin, Yuri N.,Cragg, Peter J.,Stoikov, Ivan I.
, p. 14450 - 14458 (2019)
Monosubstituted pillar[5]arenes containing a phosphonate fragment were successfully obtained in good yields. It was found that the introduction of bulky fragments containing tetra-coordinated pentavalent phosphorus atoms prevents self-Assembly of monosubstituted pillar[5]arenes and the formation of supramolecular polymers. Pillar[5]arenes with phosphonate and 1-Aminophosphonate substituents demonstrated recognition towards Na+, K+, Cs+ and Pb2+. Their ability to form complexes with these cations was evaluated by UV spectroscopy. Dynamic light scattering (DLS) revealed the formation of aggregates with K+, Cs+ and Pb2+. It was established that the substituent at the α-carbon atom of the aminophosphonate fragment played a significant role in Pb2+ binding. DLS and transmission electron microscopy revealed that Pb2+-induced aggregation formed particles with a monodisperse distribution of 0.02-0.23 and a hydrodynamic diameter of 58-178 nm.
Development and optimization of halogenated vinyl sulfones as Nrf2 activators for the treatment of Parkinson's disease
Choi, Ji Won,Kim, Siwon,Yoo, Jong Seok,Kim, Hyeon Jeong,Kim, Hyeon Ji,Kim, Byung Eun,Lee, Elijah Hwejin,Lee, Yong Sup,Park, Jong-Hyun,Park, Ki Duk
supporting information, (2021/01/06)
The Kelch-like ECH-associated protein 1 (Keap1)-Nuclear factor erythroid 2-related factor 2 (Nrf2) signaling pathway plays a pivotal role in the cellular defense system against oxidative stress by inducing antioxidant and anti-inflammatory effects. We previously developed Nrf2 activators that potentially protect the death of dopaminergic (DAergic) neuronal cells against oxidative stress in Parkinson's disease (PD). In this study, we designed and synthesized a class of halogenated vinyl sulfones by inserting halogens and pyridine to maximize Nrf2 activation efficacy. Among the synthesized compounds, (E)-3-chloro-2-(2-((2-chlorophenyl)sulfonyl)vinyl)pyridine (9d) significantly exhibited potent Nrf2 activating efficacy (9d: EC50 = 26 nM) at least 10-fold compared with the previous developed compounds (1 and 2). Furthermore, treating with 9d remarkably increased Nrf2 nuclear translocation and Nrf2 protein levels in microglial BV-2 cells. 9d was shown to induce the expression of antioxidant response genes HO-1, GCLC, GCLM, and SOD-1 at both the mRNA and protein levels and suppress proinflammatory cytokines and enzymes. Also, 9d remarkably protected DAergic neurons and restored the PD-associated motor dysfunction in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced mouse model.
Asymmetric Synthesis of Chiral 1,3-Disubstituted Allylsilanes via Copper(I)-Catalyzed 1,4-Conjugate Silylation of α,β-Unsaturated Sulfones and Subsequent Julia-Kocienski Olefination
Jia, Xue-Shun,Wang, Xian-Liang,Xiao, Jun-Zhao,Yin, Liang,Yin, Xing-Hao
, p. 1916 - 1922 (2021/06/07)
A general synthesis of chiral 1,3-disubstituted allylsilanes is established through copper(I)-catalyzed asymmetric 1,4-conjugate silylation of α,β-unsaturated sulfones and subsequent Julia-Kocienski olefination. By modification of McQuade's NHC ligand, the catalytic asymmetric conjugate silylation with a broad substrate scope is achieved in high enantioselectivity. The following Julia-Kocienski olefination proceeds smoothly at room temperature to deliver an array of chiral allylsilanes in moderate yields. More interestingly, a one-pot asymmetric synthesis with high synthetic efficiency is successfully realized. Utility of the prepared chiral 1,3-disubsituted allylsilanes is demonstrated in the asymmetric allylation of both aldehyde and aldimine. Finally, an interesting “match and mismatch” phenomenon is observed in the asymmetric allylation of chiral aldehydes.
