111752-08-0Relevant articles and documents
Synthetic studies towards N-substituted 3-vinyl-4-piperidineacetic acid derivatives
Johnson, David A.,Gribble, Gordon W.
, p. 178 - 195 (2019/05/15)
The synthesis and full characterization of two new (E)-2-butenyl)-5-amino-2-pentenoates, (Z)-4-[N-(3-buten-1-yl)benzamido]-2-buten-1-ol, and (Z)-1-chloro-4-[N-(3-buten-l-yl)benzamido]-2-butene are reported. These were designed as substrates for a projected thermal ene cyclization leading to the N-substituted 3-vinyl-4-piperidineacetic acid scaffold. Although conditions for this ene-cyclization have not yet been uncovered, the ease of preparation of these ene-cyclization substrates gives promise for their future use.
In Situ Proteome Profiling and Bioimaging Applications of Small-Molecule Affinity-Based Probes Derived from DOT1L Inhibitors
Zhu, Biwei,Zhang, Hailong,Pan, Sijun,Wang, Chenyu,Ge, Jingyan,Lee, Jun-Seok,Yao, Shao Q.
supporting information, p. 7824 - 7836 (2016/06/09)
DOT1L is the sole protein methyltransferase that methylates histone H3 on lysine 79 (H3K79), and is a promising drug target against cancers. Small-molecule inhibitors of DOT1L such as FED1 are potential anti-cancer agents and useful tools to investigate the biological roles of DOT1L in human diseases. FED1 showed excellent in vitro inhibitory activity against DOT1L, but its cellular effect was relatively poor. In this study, we designed and synthesized photo-reactive and "clickable" affinity-based probes (AfBPs), P1 and P2, which were cell-permeable and structural mimics of FED1. The binding and inhibitory effects of these two probes against DOT1L protein were extensively investigated in vitro and in live mammalian cells (in situ). The cellular uptake and sub-cellular localization properties of the probes were subsequently studied in live-cell imaging experiments, and our results revealed that, whereas both P1 and P2 readily entered mammalian cells, most of them were not able to reach the cell nucleus where functional DOT1L resides. This offers a plausible explanation for the poor cellular activity of FED1. Finally with P1/P2, large-scale cell-based proteome profiling, followed by quantitative LC-MS/MS, was carried out to identify potential cellular off-targets of FED1. Amongst the more than 100 candidate off-targets identified, NOP2 (a putative ribosomal RNA methyltransferase) was further confirmed to be likely a genuine off-target of FED1 by preliminary validation experiments including pull-down/Western blotting (PD/WB) and cellular thermal shift assay (CETSA). Minimalist "clickable" probes: Small-molecule probes P1 and P2 based on FED1 (a known DOT1L inhibitor) were developed and successfully used in experiments including live-cell imaging, in situ proteome profiling, and off-target identification (see scheme).
Palladium and copper-supported on charcoal: A heterogeneous multi-task catalyst for sequential Sonogashira-Click and Click-Heck reactions
Rossy, Cybille,Majimel, Jér?me,Delapierre, Mona Tréguer,Fouquet, Eric,Felpin, Fran?ois-Xavier
, p. 78 - 85 (2014/03/21)
This paper describes the development of one-pot sequential Sonogashira-Click and Click-Heck reactions by using Pd-Cu/C as a heterogeneous multi-task catalyst for the synthesis of heterocyclic structures. Details of the optimization studies and the substrate scope are discussed. These methodologies allow the preparation of functionalized triazoles in simple experimental conditions with inexpensive reagents.
Efficient 'one-pot' methodology for the synthesis of novel tetrahydro-β-carboline, tetrahydroisoquinoline and tetrahydrothienopyridine derivatives
Ionescu, Alexandra,Cornut, Damien,Soriano, Sébastien,Guissart, Céline,Van Antwerpen, Pierre,Jabin, Ivan
supporting information, p. 6087 - 6089 (2013/10/22)
A simple and efficient 'one-pot' methodology was developed to generate a new series of tetrahydro-β-carboline (THBC), tetrahydroisoquinoline (THIQ) and tetrahydrothienopyridine (THTP) derivatives. The key step of the methodology is based on a Pictet-Spengler type cyclization of a reactive N-carbamyliminium ion. This methodology was applied to the synthesis of a library of 32 compounds with potential anti-tumoral activity.
Reusable and highly active supported copper(i)-NHC catalysts for Click chemistry
Collinson, John-Michael,Wilton-Ely, James D. E. T.,Diez-Gonzalez, Silvia
supporting information, p. 11358 - 11360 (2013/12/04)
Immobilised [Cu(NHC)] catalysts are reported for the preparation of 1,2,3-triazoles. In addition to showing outstanding catalytic activity, the catalyst systems are easy to prepare and can be recycled many times.
Complexes: Synthesis, characterization and catalytic activities in reduction reactions and Click Chemistry. on the advantage of using well-defined catalytic systems
Diez-Gonzalez, Silvia,Escudero-Adan, Eduardo C.,Benet-Buchholz, Jordi,Stevens, Edwin D.,Slawin, Alexandra M. Z.,Nolan, Steven P.
supporting information; experimental part, p. 7595 - 7606 (2010/09/16)
The preparation of three series of [(NHC)CuX] complexes (NHC = N-heterocyclic carbene, X = Cl, Br, or I) is reported. These syntheses are high yielding and only use readily available starting materials. The prepared complexes were spectroscopically and st
[(NHC)2Cu]X complexes as efficient catalysts for azide-alkyne click chemistry at low catalyst loadings
Diez-Gonzlez, Silvia,Nolan, Steven P.
supporting information; experimental part, p. 8881 - 8884 (2009/05/26)
(Chemical Equation Presented) La click, c'est chic! A catalytic system based on an [(NHC)2Cu]X complex (NHC=N-heterocyclic carbene) was developed for the [3+2] cycloaddition of azides with alkynes under click conditions (see scheme). This syste
A [(NHC)CuCl] complex as a latent Click catalyst
Diez-Gonzalez, Silvia,Stevens, Edwin D.,Nolan, Steven P.
supporting information; experimental part, p. 4747 - 4749 (2009/03/12)
A latent catalyst for the [3+2] cycloaddition reaction of azides and alkynes has been developed in accordance with the principles of Click chemistry. The Royal Society of Chemistry.
(NHC)copper(I)-catalyzed [3+2] cycloaddition of azides and Mono- Or disubstituted alkynes
Diez-Gonzalez, Silvia,Correa, Andrea,Cavallo, Luigi,Nolan, Steven P.
, p. 7558 - 7564 (2007/10/03)
A versatile and highly efficient catalyst for the Huisgen cycloaddition reaction has been developed. Previously isolated or in situ generated azides yielded 1,2,3-triazoles with differently substituted alkynes in the presence of a [(NHC)CuBr] complex (NHC
ETUDE DE LA CHIMIOSELECTIVITE DE LA REACTION DES DICHLOROBORANES AVEC LES AZIDES FONCTIONNELS: UNE SYNTHESE EFFICACE D'AMINES SECONDAIRES FONCTIONNALISEES.
Carboni, B.,Vaultier, M.,Carrie, R.
, p. 1799 - 1810 (2007/10/02)
The reaction of cyclohexyldichloroborane, used as a model, with a wide variety of functionalized azides has been studied.It has been shown to be an efficient synthesis of secondary amines in terms of chemioselectivity, yields and wide applicability.
