(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 manufacturers
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| | (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 Basic information |
| Product 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 | | Synonyms: | (R)-(-)-JQ1 Enantiomer;(R)-(-)-JQ1;(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]diazepin-6-yl)acetate;(-)-JQ-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];JQ-1;JQ1;-JQ1;JQ 1;(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 | | CAS: | 1268524-71-5 | | MF: | C23H25ClN4O2S | | MW: | 456.99 | | EINECS: | | | Product Categories: | Inhibitor | | Mol File: | 1268524-71-5.mol | ![(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 Structure](CAS/GIF/1268524-71-5.gif) |
| | (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 Chemical Properties |
| Boiling point | 610.4±65.0 °C(Predicted) | | density | 1.33 | | storage temp. | 2-8°C | | solubility | DMSO: soluble20mg/mL, clear | | pka | 2.05±0.60(Predicted) | | form | powder | | 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 |
| WGK Germany | WGK 3 | | Storage Class | 11 - Combustible Solids |
| | (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 Usage And Synthesis |
| 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. 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. | | 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 |
| | (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 Preparation Products And Raw materials |
| Raw materials | (+)-JQ-1-->Fmoc-Asp(OtBu)-OH-->Acethydrazide-->(±)-JQ1-->1H-Thieno[2,3-e]-1,4-diazepine-3-acetic acid, 5-(4-chlorophenyl)-2,3-dihydro-6,7-diMethyl-2-oxo-, 1,1-diMethylethyl ester, (3S)--->Butanoic acid, 3-aMino-4-[[3-(4-chlorobenzoyl)-4,5-diMethyl-2-thienyl]aMino]-4-oxo-, 1,1-diMethylethyl ester, (3S)--->2-AMino-3-(p-chlorobenzoyl)-4,5-diMethylthiophene-->Butanoic acid, 4-[[3-(4-chlorobenzoyl)-4,5-diMethyl-2-thienyl]aMino]-3-[[(9H-fluoren-9-ylMethoxy)carbonyl]aMino]-4-oxo-, 1,1-diMethylethyl ester, (3S)- |
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