1074-16-4Relevant articles and documents
Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols
Meng, Shuyu,Wang, Quanrui,Zheng, Jie
supporting information, p. 1481 - 1489 (2021/07/02)
The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanals with BF3·Et2O results in an intramolecular Prins reaction affording intermediary benzyl carbenium ions, which are then trapped by a variety of electron-ric
Discovery of TAK-981, a First-in-Class Inhibitor of SUMO-Activating Enzyme for the Treatment of Cancer
Langston, Steven P.,Grossman, Stephen,England, Dylan,Afroze, Roushan,Bence, Neil,Bowman, Douglas,Bump, Nancy,Chau, Ryan,Chuang, Bei-Ching,Claiborne, Christopher,Cohen, Larry,Connolly, Kelly,Duffey, Matthew,Durvasula, Nitya,Freeze, Scott,Gallery, Melissa,Galvin, Katherine,Gaulin, Jeffrey,Gershman, Rachel,Greenspan, Paul,Grieves, Jessica,Guo, Jianping,Gulavita, Nanda,Hailu, Shumet,He, Xingyue,Hoar, Kara,Hu, Yongbo,Hu, Zhigen,Ito, Mitsuhiro,Kim, Mi-Sook,Lane, Scott Weston,Lok, David,Lublinsky, Anya,Mallender, William,McIntyre, Charles,Minissale, James,Mizutani, Hirotake,Mizutani, Miho,Molchinova, Nina,Ono, Koji,Patil, Ashok,Qian, Mark,Riceberg, Jessica,Shindi, Vaishali,Sintchak, Michael D.,Song, Keli,Soucy, Teresa,Wang, Yana,Xu, He,Yang, Xiaofeng,Zawadzka, Agatha,Zhang, Ji,Pulukuri, Sai M.
supporting information, p. 2501 - 2520 (2021/04/02)
SUMOylation is a reversible post-translational modification that regulates protein function through covalent attachment of small ubiquitin-like modifier (SUMO) proteins. The process of SUMOylating proteins involves an enzymatic cascade, the first step of which entails the activation of a SUMO protein through an ATP-dependent process catalyzed by SUMO-activating enzyme (SAE). Here, we describe the identification of TAK-981, a mechanism-based inhibitor of SAE which forms a SUMO-TAK-981 adduct as the inhibitory species within the enzyme catalytic site. Optimization of selectivity against related enzymes as well as enhancement of mean residence time of the adduct were critical to the identification of compounds with potent cellular pathway inhibition and ultimately a prolonged pharmacodynamic effect and efficacy in preclinical tumor models, culminating in the identification of the clinical molecule TAK-981.
Reliably Regioselective Dialkyl Ether Cleavage with Mixed Boron Trihalides
Atienza, Bren Jordan P.,Truong, Nam,Williams, Florence J.
, p. 6332 - 6335 (2018/10/09)
A protocol for the regioselective cleavage of unsymmetrical alkyl ethers to generate alkyl alcohol and alkyl bromide products is described. A mixture of trihaloboranes triggers this conversion and exhibits improved reactivity profiles (regioselectivity and yield) compared with BBr3 alone. Additionally, this procedure allows the efficient synthesis of (B-Cl) dialkyl boronate esters. There are limited methods to generate acyclic dialkoxyboryl chlorides, and these intermediates constitute important synthons in main-group chemistry.