3313-84-6Relevant articles and documents
Electrochemical cross-coupling reactions of sodium arenesulfinates with thiophenols and phenols
Ma, Jinfeng,Xu, Pan,Zhong, Zijian,Zhou, Aihua
supporting information, (2021/10/26)
A green electrochemical oxidative cross-coupling protocol for the generation of thiosulfonates and sulfonate esters using sodium arenesulfinates and thiophenols/phenols is disclosed. The protocol involves using inorganic and non-toxic NaI as both redox catalyst and supporting electrolyte at room temperature without oxidant and base. The reactions provide good yields of products and tolerate broad substrate scope. The mechanistic studies revealed that the reactions proceed via a radical pathway for the formation of SO2–S and SO2–O bonds.
Development of succinimide-based inhibitors for the mitochondrial rhomboid protease PARL
Andrews, Charlotte L.,Cardozo, Joaquin M.,Chow, Alyssa S.,Crainic, Jennifer A.,Parsons, William H.,Rutland, Nicholas T.,Sheehan, Brendan K.
supporting information, (2021/08/04)
While the biochemistry of rhomboid proteases has been extensively studied since their discovery two decades ago, efforts to define the physiological roles of these enzymes are ongoing and would benefit from chemical probes that can be used to manipulate the functions of these proteins in their native settings. Here, we describe the use of activity-based protein profiling (ABPP) technology to conduct a targeted screen for small-molecule inhibitors of the mitochondrial rhomboid protease PARL, which plays a critical role in regulating mitophagy and cell death. We synthesized a series of succinimide-containing sulfonyl esters and sulfonamides and discovered that these compounds serve as inhibitors of PARL with the most potent sulfonamides having submicromolar affinity for the enzyme. A counterscreen against the bacterial rhomboid protease GlpG demonstrates that several of these compounds display selectivity for PARL over GlpG by as much as two orders of magnitude. Both the sulfonyl ester and sulfonamide scaffolds exhibit reversible binding and are able to engage PARL in mammalian cells. Collectively, our findings provide encouraging precedent for the development of PARL-selective inhibitors and establish N-[(arylsulfonyl)oxy]succinimides and N-arylsulfonylsuccinimides as new molecular scaffolds for inhibiting members of the rhomboid protease family.
Deprotection of durable benzenesulfonyl protection for phenols — efficient synthesis of polyphenols
Alam, Mohammad Shariful,Koo, Sangho
supporting information, p. 247 - 254 (2018/01/08)
A robust protection method for phenol was demonstrated by the use of durable benzenesulfonyl group, which survives various harsh reaction conditions using Grignard reagent, organolithium reagent, metal alkoxide, phosgene, mineral, and Lewis acids. A facile deprotection condition utilizing pulverized KOH (5 equiv) and t-BuOH (10 equiv) in hot toluene makes this protocol as a practical method, which can be applied to the multistep synthesis of biologically and medicinally important polyphenol compounds.
