41029-44-1Relevant articles and documents
Synthesis and Multiplexed Activity Profiling of Synthetic Acylphloroglucinol Scaffolds
Boyce, Jonathan H.,Reisman, Benjamin J.,Bachmann, Brian O.,Porco, John A.
, p. 1263 - 1272 (2021)
Reported here are novel formic-acid-mediated rearrangements of dearomatized acylphloroglucinols to access a structurally diverse group of synthetic acylphloroglucinol scaffolds (SASs). Density-functional theory (DFT) optimized orbital and stereochemical analyses shed light on the mechanism of these rearrangements. Products were evaluated by multiplexed activity profiling (MAP), an unbiased platform which assays multiple biological readouts simultaneously at single-cell resolution for markers of cell signaling, and can aid in distinguishing genuine activity from assay interference. MAP identified a number of SASs that suppressed pS6 (Ser235/236), a marker for activation of the mTOR and ERK signaling pathways. These results illustrate how biomimetic synthesis and multiplexed activity profiling can reveal the pharmacological potential of novel chemotypes by diversity-oriented synthesis.
Water-Soluble N-Heterocyclic Carbene-Protected Gold Nanoparticles: Size-Controlled Synthesis, Stability, and Optical Properties
Salorinne, Kirsi,Man, Renee W. Y.,Li, Chien-Hung,Taki, Masayasu,Nambo, Masakazu,Crudden, Cathleen M.
, p. 6198 - 6202 (2017)
NHC-AuI complexes were used to prepare stable, water-soluble, NHC-protected gold nanoparticles. The water-soluble, charged nature of the nanoparticles permitted analysis by polyacrylamide gel electrophoresis (PAGE), which showed that the nanoparticles were highly monodisperse, with tunable core diameters between 2.0 and 3.3 nm depending on the synthesis conditions. Temporal, thermal, and chemical stability of the nanoparticles were determined to be high. Treatment with thiols caused etching of the particles after 24 h; however larger plasmonic particles showed greater resistance to thiol treatment. These water-soluble, bio-compatible nanoparticles are promising candidates for use in photoacoustic imaging, with even the smallest nanoparticles giving reliable photoacoustic signals.
A Simple Preparation of Alkyl Trifluoromethanesulfonates (Triflates) from Alkyl Trimethylsilyl Ethers
Aubert, Corinne,Begue, Jean-Pierre
, p. 759 - 760 (1985)
Several alkyl trifluoromethanesulfonates (triflates) 2 are prepared by reacting alkyl trimethylsilyl ethers 1 with trifluoromethanesulfonic anhydride.The triflates 2 can be used for further reactions without isolation, as illustrated in the preparation of the ether 3 and cumene (4).
Competitive pathways in the reaction of lithium oxy-ortho-quinodimethanes and fischer alkoxy alkynyl carbene complexes: Synthesis of highly functionalised seven-membered benzocarbocycles
Garcia-Garcia, Patricia,Novillo, Carlos,Fernandez-Rodriguez, Manuel A.,Aguilar, Enrique
supporting information; experimental part, p. 564 - 571 (2011/03/18)
Up to four different outcomes have been found for the reaction between 1-oxy-ortho-quinodimethanes (oQDMs) and alkoxy alkynyl Fischer carbene complexes (FCCs). The product formed depends on the structure of both reagents and on the reaction solvent. The pathways can be topologically classified as a [4C+2C], a [3(2C+O)+3C], and two different [4C+3C] processes and, in all these sequences, 1-oxy-oQDMs behave as enolates or as vinylogous enolates. The reaction of Choy and Yang's unsubstituted oQDM 1 with tungsten alkynyl FCCs is solvent controlled; thus, selective formation of benzocycloheptenones can be achieved in THF, whereas exclusive synthesis of benzocycloheptene ketals is reached in diethyl ether. On the other hand, THF is the solvent of choice to form benzocycloheptene ketals when an alkyl or aryl group is placed at position 1 of the oQDM in its reaction with tungsten carbene complexes; however, a pyranylidene carbene complex is formed when a chromium carbene complex is used. Alternatively, the presence of bulky alkoxy groups in the FCC component favours a Diels-Alder aromatisation sequence, which leads to 1-naphthyl FCCs. Furthermore, the isolation and the characterisation of several deuterated compounds by labelling experiments have provided some insight into the reaction pathways, and mechanisms consistent with those findings have been established and several reaction intermediates have been identified.
