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912131

Sigma-Aldrich

2-Chloro-1-(6-methoxy-1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-one

≥95%

Sinonimo/i:

1-(Chloroacetyl)-1,2,3,4-tetrahydro-6-quinolinyl methyl ether, 2-Chloro-1-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one, Electrophilic scout fragment, KB02, Scout fragment for targetable cysteine

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About This Item

Formula empirica (notazione di Hill):
C12H14ClNO2
Numero CAS:
57368-84-0
Peso molecolare:
239.70
Numero MDL:
MFCD09376367
Codice UNSPSC:
12352200
NACRES:
NA.22

Livello qualitativo

100

Saggio

≥95%

Stato

chunks

Temperatura di conservazione

2-8°C

Stringa SMILE

ClCC(=O)N1CCCc2c1ccc(c2)OC

InChI

1S/C12H14ClNO2/c1-16-10-4-5-11-9(7-10)3-2-6-14(11)12(15)8-13/h4-5,7H,2-3,6,8H2,1H3
XJPUWRWIBSSPSL-UHFFFAOYSA-N

Categorie correlate

Applicazioni

2-Chloro-1-(6-methoxy-1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-one is a cysteine-reactive small-molecule fragment for chemoproteomic and ligandability studies for both traditionally druggable proteins as well as "undruggable," or difficult-to-target, proteins. This fragment electrophile, or "scout" fragment, can be used alone in fragment-based covalent ligand discovery or incorporated into bifunctional tools such as electrophilic PROTAC® molecules for targeted protein degradation as demonstrated by the Cravatt Lab Lab for E3 ligase discovery.

Altre note

Technology Spotlight: Proteomic Ligandability Assessment

The Proteome-Wide Potential for Reversible Covalency at Cysteine

Electrophilic PROTACs that degrade nuclear proteins by engaging DCAF16

Proteome-wide covalent ligand discovery in native biological systems

Note legali

PROTAC is a registered trademark of Arvinas Operations, Inc., and is used under license

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Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Kristine Senkane et al.
Angewandte Chemie (International ed. in English), 58(33), 11385-11389 (2019-06-22)
Reversible covalency, achieved with, for instance, highly electron-deficient olefins, offers a compelling strategy to design chemical probes and drugs that benefit from the sustained target engagement afforded by irreversible compounds, while avoiding permanent protein modification. Reversible covalency has mainly been
Keriann M Backus et al.
Nature, 534(7608), 570-574 (2016-06-17)
Small molecules are powerful tools for investigating protein function and can serve as leads for new therapeutics. Most human proteins, however, lack small-molecule ligands, and entire protein classes are considered 'undruggable'. Fragment-based ligand discovery can identify small-molecule probes for proteins
Xiaoyu Zhang et al.
Nature chemical biology, 15(7), 737-746 (2019-06-19)
Ligand-dependent protein degradation has emerged as a compelling strategy to pharmacologically control the protein content of cells. So far, however, only a limited number of E3 ligases have been found to support this process. Here, we use a chemical proteomic

Articoli

Proteomic Ligandability Assessment

Ligandability describes the propensity of a protein target to bind a small molecule with high affinity. It is a precursor to evaluating druggability, which requires more advanced translational pharmacological effects and drug-like properties in vivo.

Global Trade Item Number

SKUGTIN
912131-100MG4061841783886

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