335281-13-5Relevant academic research and scientific papers
Antioxidant, Anti-inflammatory, and Neuroprotective Effects of Novel Vinyl Sulfonate Compounds as Nrf2 Activator
Choi, Ji Won,Shin, Su Jeong,Kim, Hyeon Ji,Park, Jong-Hyun,Kim, Hyeon Jeong,Lee, Elijah Hwejin,Pae, Ae Nim,Bahn, Yong Sun,Park, Ki Duk
supporting information, p. 1061 - 1067 (2019/06/24)
The main pathway responsible for cellular regulation against oxidative stress is nuclear factor E2-related factor-2 (Nrf2) signaling. We previously synthesized and reported a novel vinyl sulfone (1) as an Nrf2 activator with therapeutic potential for Parkinson's disease (PD). In this study, we changed the vinyl sulfone to vinyl sulfonamide or vinyl sulfonate to improve Nrf2 activating efficacy. We observed that the introduction of vinyl sulfonamide led to a reduction of the effects on Nrf2 activation, whereas vinyl sulfonate compounds exhibited superior activity compared to the vinyl sulfone compounds. Among the vinyl sulfonates, 3c exhibited 6.9- and 83.5-fold higher effects on Nrf2 activation than the corresponding vinyl sulfone (1) and vinyl sulfonamide (2c), respectively. Compound 3c was confirmed to induce expression of the Nrf2-dependent antioxidant enzymes at the protein level in cells. In addition, 3c mitigated PD-associated behavioral deficits by protecting DAergic neurons in the MPTP-induced mouse model of PD.
[3+2] Cycloaddition of an Azomethyne Ylide and Vinyl Sulfonyl Fluorides ― an Approach to Pyrrolidine-3-sulfonyl Fluorides
Mykhalchuk, Volodymyr L.,Yarmolchuk, Vladimir S.,Doroschuk, Roman O.,Tolmachev, Andrey A.,Grygorenko, Oleksandr O.
, p. 2870 - 2876 (2018/06/21)
[3+2] Cycloaddition reactions of vinyl sulfonyl fluorides with an in-situ generated nonstabilized azomethine ylide is described for the first time. The resulting pyrrolidine-3-sulfonyl fluorides were obtained in 50–83 % yield on a scale of up to 25 g. Their utility as reagents for sulfur(VI)–fluoride exchange (SuFEx) and some other transformations was also demonstrated.
Sulfonylated aminothiazoles as new small molecule inhibitors of protein phosphatases
Wipf, Peter,Aslan, Diana C.,Southwick, Eileen C.,Lazo, John S.
, p. 313 - 317 (2007/10/03)
Based on a previously identified lead structure, SC-ααδ9, we have developed a versatile new chemical scaffold that can be readily modified to generate libraries of both Tyr and dual specificity phosphatase inhibitors with reduced molecular weight and lipophilicity. The most potent analogue identified to date, aminothiazole 8z, inhibits the dual specificity phosphatase Cdc25B with a Ki of 4.6 ± 0.4 μM and a Hill coefficient of 2.
