3034-54-6Relevant articles and documents
Design and characterization of a heterocyclic electrophilic fragment library for the discovery of cysteine-targeted covalent inhibitors
Keeley,ábrányi-Balogh,Keseru
supporting information, p. 263 - 267 (2019/03/05)
A fragment library of electrophilic small heterocycles was characterized through cysteine-reactivity and aqueous stability tests that suggested their potential as covalent warheads. The analysis of theoretical and experimental descriptors revealed correlations between the electronic properties of the heterocyclic cores and their reactivity against GSH that are helpful in identifying suitable fragments for cysteines with specific nucleophilicity. The most important advantage of these fragments is that they show only minimal structural differences from non-electrophilic counterparts. Therefore, they could be used effectively in the design of targeted covalent inhibitors with minimal influence on key non-covalent interactions.
Deprotonative metalation of five-membered aromatic heterocycles using mixed lithium-zinc species
L'Helgoual'ch, Jean-Martial,Seggio, Anne,Chevallier, Floris,Yonehara, Mitsuhiro,Jeanneau, Erwann,Uchiyama, Masanobu,Mongin, Florence
, p. 177 - 183 (2008/09/17)
(Equation Presented) Deprotonation of benzoxazole, benzothiazole, benzo[b]thiophene, benzo[b]furan, N-Boc-protected indole and pyrrole, and N-phenylpyrazole using an in situ mixture of ZnCl2·TMEDA (0.5 equiv) and lithium 2,2,6,6-tetramethylpipe
Synthesis of High Carbon Materials from Acetylenic Precursors. Preparation of Aromatic Monomers Bearing Multiple Ethynyl Groups
Neenan, Thomas X.,Whitesides, George M.
, p. 2489 - 2496 (2007/10/02)
The synthesis of polyethynyl aromatics as starting materials for the preparation of highly cross-linked organic solids containing high atom fractions of carbon is described.Treatment of bromo- and iodoaromatic compounds with (trimethylsilyl)acetylene (TMSA) in the presence of palladium(O) and copper(I) in amine solvents yields (trimethylsilyl)ethynyl-substituted aromatics.The TMS protecting groups can be removed by hydrolysis with mild base.Compounds prepared by using this technique include 1,3-diethynylbenzene, 2,5-diethynylthiophene, 1,3-diethynyltetrafluorobenzene, 1,4-diethynyltetrafluorobenzene, 2-ethynylthiazole, 2,4-diethynylthiazole, 2,7-diethynylnaphthalene, hexakis((trimethylsilyl)ethynyl)benzene, tetraethynylthiophene, 2,5-bis((trimethylsilyl)ethynyl)-3,4-bis(3-hydroxy-3-methyl-1-butynyl)thiophene, 2,5-diethynyl-3,4-bis(3-hydroxy-3-methyl-1-butynyl)thiophene, 2,5-bis(4-(2-thienyl)butadiynyl)-3,4-bis(3-hydroxy-3-methyl-1-butynyl)thiophene, and 2,5-bis-(4-(2-thienyl)butadiynyl)-3,4-diethynylthiophene.