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Chemical Structure| 128-08-5 Chemical Structure| 128-08-5
Chemical Structure| 128-08-5

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Synonyms: 1-Bromo-2,5-pyrrolidinedione

4.5 *For Research Use Only !

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Product Citations

Product Citations      Show More

Wilms, Gerrit ; Schofield, Kevin ; Maddern, Shayna ; Foley, Christopher ; Shaw, Yeng ; Smith, Breland , et al.

Abstract: Small-molecule-induced protein degradation has emerged as a promising pharmacological modality for inactivating disease-relevant protein kinases. DYRK1A and DYRK1B are closely related protein kinases that are involved in pathological processes such as neurodegeneration, cancer development, and adaptive immune homeostasis. Herein, we report the development of the first DYRK1 proteolysis targeting chimeras (PROTACs) that combine a new ATP-competitive DYRK1 inhibitor with ligands for the component cereblon (CRBN) to induce ubiquitination and subsequent proteasomal degradation of DYRK1A and DYRK1B. The lead compound (DYR684) promoted fast, efficient, potent, and selective degradation of DYRK1A in cell-based assays. Interestingly, an enzymatically inactive splicing variant of DYRK1B (p65) resisted degradation. Compared to competitive kinase inhibition, targeted degradation of DYRK1 by DYR684 provided improved suppression of downstream signaling. Collectively, our results identify DYRKs as viable targets for PROTAC-mediated degradation and qualify DYR684 as a useful chemical probe for DYRK1A and DYRK1B.

Purchased from AmBeed: ; ; ;

Górski, Krzysztof ; Pejov, Ljupcho ; Jørgensen, Kåre B ; Knysh, Iryna ; Jacquemin, Denis ; Gryko, Daniel T

Abstract: Here we present a highly versatile synthetic strategy based on twofold 6π-electrocyclization accompanied with HBr elimination as a novel approach towards centrosymmetric multi-heteroatom-doped nanographenes build around an electron-rich 1,4-dihydropyrrolo[3,2-b]pyrrole core. A straightforward synthesis from readily available substrates offers a unique possibility of fusing the 1,4-dihydropyrrolo[3,2-b]pyrrole subunit not only with carbocyclic building blocks, such as electron-deficient phenanthrenes, chrysenes, or [4]helicenes, but also with heterocyclic systems, such asbenzo[b]furan and 5-thiatruxene. The clear advantage of this strategy is that there is no requirement to assemble complex scaffolds possessing bromoaryl units since bromine atom is introduced by bromination of 1,4-dihydropyrrolo[3,2-b]pyrrole core which, because of its exceptionally electron-rich character, is straightforward reaction. The obtained χ-shaped and S-shaped nanographenes containing 10or more fused rings, exhibit visible-range emissions characterized by fluorescence quantum yields reaching 48%. Computational studies of the reaction mechanism revealed that the 6π-electrocyclization is kinetically favourable over photo-induced direct arylation. Steadystate UV/Visible spectroscopy reveals that upon photoexcitation, the prepared S-shaped N-doped nanographenes undergo mostly radiative relaxation leading to large fluorescence quantum yields. We anticipate that this chemistry will empower the creation of new materials with various functionalities.

Keywords: Dyes/Pigments ; Photochemistry ; Nanographenes ; Pyrrole ; Fluorescence

Purchased from AmBeed: ; ; ;

Robert Kawȩcki ;

Abstract: N-Sulfenylimines (sulfenimines, thiooximes, N-alkylidenesulfenamides) were efficiently synthesized through the reaction of primary amines and disulfides with NBS or bromine. This reaction can be carried out in an open flask at room temperature without the need for any transition-metal-containing additives. The use of thiols instead of disulfides gave similar results. A wide range of amines were reacted with aryl and alkyldisulfides, resulting in the formation of sulfenimines in a yield of 44–99%.

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Product Details of NBS

CAS No. :128-08-5
Formula : C4H4BrNO2
M.W : 177.98
SMILES Code : O=C(CC1)N(Br)C1=O
Synonyms :
1-Bromo-2,5-pyrrolidinedione
MDL No. :MFCD00005510
InChI Key :PCLIMKBDDGJMGD-UHFFFAOYSA-N
Pubchem ID :67184

Safety of NBS

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H272-H290-H315-H317-H319-H341-H400
Precautionary Statements:P201-P202-P210-P220-P221-P234-P261-P264-P272-P273-P280-P302+P352-P305+P351+P338-P308+P313-P333+P313-P337+P313-P370+P378-P390-P391-P405-P406-P501
Class:8(5.1)
UN#:3084
Packing Group:

Application In Synthesis of NBS

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 128-08-5 ]
  • Downstream synthetic route of [ 128-08-5 ]

[ 128-08-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 128-08-5 ]
  • [ 6267-02-3 ]
  • [ 1333316-35-0 ]
References: [1] Patent: US2012/319052, 2012, A1, .
 

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