| Identification | Back Directory | [Name]
(R)-(-)-tert-Butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate | [CAS]
1268524-71-5 | [Synonyms]
(-)-JQ-1
(R)-(-)-JQ1
JQ-1;JQ1;-JQ1;JQ 1
(R)-(-)-JQ1 Enantiomer
(-)-JQ-1;(R)-(-)-JQ1 ENANTIOMER
(R)-tert-Butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno-[3,2-f][1,2,4]triazolo[4,3-a][1
(R)-(-)-tert-Butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]
(R)-(-)-tert-Butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate
(6R)-4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid 1,1-dimethylethyl ester
6H-Thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid, 4-(4-chlorophenyl)-2,3,9-trimethyl-, 1,1-dimethylethyl ester, (6R)- | [Molecular Formula]
C23H25ClN4O2S | [MDL Number]
MFCD22124456 | [MOL File]
1268524-71-5.mol | [Molecular Weight]
456.99 |
| Chemical Properties | Back Directory | [Boiling point ]
610.4±65.0 °C(Predicted) | [density ]
1.33 | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble20mg/mL, clear | [form ]
powder | [pka]
2.05±0.60(Predicted) | [color ]
white to beige | [InChI]
1S/C23H25ClN4O2S/c1-12-13(2)31-22-19(12)20(15-7-9-16(24)10-8-15)25-17(11-18(29)30-23(4,5)6)21-27-26-14(3)28(21)22/h7-10,17H,11H2,1-6H3/t17-/m1/s1 | [InChIKey]
DNVXATUJJDPFDM-QGZVFWFLSA-N | [SMILES]
O=C(OC(C)(C)C)C[C@@H]1C2=NN=C(C)N2C(SC(C)=C3C)=C3C(C4=CC=C(Cl)C=C4)=N1 |
| Hazard Information | Back Directory | [Description]
The bromodomain and extra terminal domain (BET) family of proteins, including BRD2, BRD3, and BRD4, play a key role in many cellular processes, including inflammatory gene expression, mitosis, and viral/host interaction by controlling the assembly of histone acetylation-dependent chromatin complexes. (±)-JQ1 displaces BET proteins from chromatin by competitively binding to the acetyl-lysine recognition pocket of BET bromodomains.1,2 The (−)-JQ1 stereoisomer has no appreciable affinity to BET bromodomains, whereas enantiomerically pure (+)-JQ1 binds to BRD4 bromodomains 1 and 2 with Kd values of ~50 and 90 nM, respectively.1 | [Uses]
(R)-(-)-Tert-butyl 2-(4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate is the enantiomer of (S)-(+)-Tert-butyl 2-(4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate (T117580), which is BET bromodomain inhibitor, also activates HIV latency through antagonizing Brd4 inhibition of Tat-transactivation. | [Definition]
ChEBI: LSM-6333 is an organonitrogen heterocyclic compound, an organosulfur heterocyclic compound and a tert-butyl ester. | [General Description]
JQ1 is a member of the triazolo-diazepine compound family which functions as a pan-BET (bromodomain and extra-terminal motif) family inhibitor. Its core structure is composed of thienodiazepine. | [Biochem/physiol Actions]
(-)-JQ1 is the negative control probe for (+)-JQ1, the active enantiomer of (+/-)-JQ1, which is a potent and selective BET bromodomain inhibitor. (-)-JQ1 shows no significant interaction with BRD1-4 or other bromodomains.For characterization details of the active probe, (+)-JQ1, please visit the JQ1 probe summary on the Structural Genomics Consortium (SGC) website.(+)-JQ1, the active enantiomer, is available from Sigma. To learn more about and purchase (+)-JQ1, click here.To learn about other SGC chemical probes for epigenetic targets, visit sigma.com/sgc | [storage]
Store at -20°C | [References]
[1] PANAGIS FILIPPAKOPOULOS. Selective inhibition of BET bromodomains[J]. Nature, 2010, 468 7327: 1067-1073. DOI: 10.1038/nature09504
[2] MARGIT ROSNER Markus H. Targeting epigenetic readers in cancer.[J]. New England Journal of Medicine, 2012, 367 18: 1764-1765. DOI: 10.1056/nejmc1211175 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
(R)-(-)-tert-Butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate(1268524-71-5)MS
(R)-(-)-tert-Butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate(1268524-71-5)1HNMR
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Sigma-Aldrich
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021-61415566 800-8193336 |
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https://www.sigmaaldrich.cn |
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