1428743-70-7Relevant articles and documents
Weakly nucleophilic potassium aryltrifluoroborates in palladium-catalyzed Suzuki-Miyaura reactions? Relative reactivity of K[4-RC6F4BF3] and the role of silver-assistance in acceleration of transmetallation
Bardin, Vadim V.,Shabalin, Anton Yu,Adonin, Nicolay Yu
, p. 608 - 616 (2015)
Small differences in the reactivity of weakly nucleophilic potassium aryltrifluoroborates are revealed in the silver-assisted Pd-catalyzed cross-coupling of K[4-RC6F4BF3] (R = H, Bu, MeO, EtO, PrO, iPrO, BuO, t-BuO, CH2=CHCH2O, PhCH2O, PhCH2CH2O, PhO, F, pyrazol-1-yl, pyrrol-1-yl, and indol-1-yl) with ArX (4-BrC6H4CH3, 4-IC6H4F and 3-IC6H4F). An assumed role of silver(I) compounds AgmY (Y = O, NO3, SO4, BF4, F) consists in polarization of the Pd-X bond in neutral complex ArPdLnX with the generation of the related transition state or formation of [ArPdLn][XAgmY] with a highly electrophilic cation and subsequent transmetallation with the weakly nucleophilic borate. Efficiency of AgmY as a polarizing agent decreases in order Ag2O > AgNO3 ≈ Ag2SO4 > Ag[BF4] > AgF. No clear correlation between the reactivity of K[4-RC6F4BF3] and substituent electron parameters, σI and σR °, of the aryl group 4-RC6F4 was found.
Inhibiting a dynamic viral protease by targeting a non-catalytic cysteine
Arkin, Michelle R.,Bohn, Markus-Frederik,Chuo, Shih-Wei,Connelly, Emily J.,Craik, Charles S.,Hulce, Kaitlin R.,Jaishankar, Priyadarshini,Lee, Gregory M.,Ongpipattanakul, Chayanid,Renslo, Adam R.,Volk, Regan F.,Wucherer, Kristin
supporting information, p. 785 - 19,798 (2022/05/27)
Viruses are responsible for some of the most deadly human diseases, yet available vaccines and antivirals address only a fraction of the potential viral human pathogens. Here, we provide a methodology for managing human herpesvirus (HHV) infection by covalently inactivating the HHV maturational protease via a conserved, non-catalytic cysteine (C161). Using human cytomegalovirus protease (HCMV Pr) as a model, we screened a library of disulfides to identify molecules that tether to C161 and inhibit proteolysis, then elaborated hits into irreversible HCMV Pr inhibitors that exhibit broad-spectrum inhibition of other HHV Pr homologs. We further developed an optimized tool compound targeted toward HCMV Pr and used an integrative structural biology and biochemical approach to demonstrate inhibitor stabilization of HCMV Pr homodimerization, exploiting a conformational equilibrium to block proteolysis. Irreversible HCMV Pr inhibition disrupts HCMV infectivity in cells, providing proof of principle for targeting proteolysis via a non-catalytic cysteine to manage viral infection.
Synthesis of K[4-ROC6F4BF3] from potassium pentafluorophenyltrifluoroborate and O-nucleophiles
Shabalin, Anton Yu.,Adonin, Nicolay Yu.,Bardin, Vadim V.,Prikhod'Ko, Sergey A.,Timofeeva, Maria N.,Bykova, Maria V.,Parmon, Valentin N.
, p. 82 - 87 (2013/05/22)
A new route to potassium polyfluoroaryltrifluoroborates, K[4-ROC 6F4BF3], consisting in the nucleophilic alkoxydefluorination of K[C6F5BF3] with MOR (M = K, Na) in a polar aprotic solvent is suggested. Reaction of K[C 6F5BF3] with KO-t-Bu proceeds smoothly at 25 °C in DME, but the attempted alkoxydefluorination of K[C6F 5BF3] with other NaOR at 30 °C in DME failed. A series of K[4-ROC6F4BF3] (R = Me, Et, Pr, i-Pr, Bu, PhCH2) is prepared using the corresponding sodium alkoxides in DMF at 130 °C in 80-90% isolated yield. Salt K[4-CH2CHCH 2OC6F4BF3] is prepared at 100 °C whereas at 130 °C formation of 2,3,5,6-C6F4HOCH 2CHCH2 occurs. Salt K[4-PhOC6F 4BF3] is obtained in 82% yield using KOPh (2 equivalents) in DMSO at 130 °C.
