(±)-JQ1

Base Information

• Chemical Name: (±)-JQ1
• CAS No.: 1268524-69-1
• Molecular Formula: C23H25ClN4O2S
• Molecular Weight: 456.996
• Mol file: 1268524-69-1.mol

Synonyms: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;(+/-)-SGCBD01;[(R,S)-4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-1-thia-5,7,8,9a-tetraaza-cyclopenta[e]azulen-6-yl]-acetic acid tert-butyl ester

Chemical Property of (±)-JQ1

Chemical Property:

• Boiling Point: 610.4±65.0 °C(Predicted)
• PKA: 2.05±0.60(Predicted)
• PSA: 97.61000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 4.96690
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble2mg/mL, clear (warmed)

Purity/Quality:

97% ^*data from raw suppliers

rac-tert-Butyl2-(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 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: (±) JQ1 (1268524-69-1) is a potent BET bromodomain inhibitor. IC50 = 17.7, 32.6, 76.9 and 12942 nM respectively for BRD2 (N-terminal (N)), BRD4 (C-terminal (C)), BRD4 (N) and CREBBP respectively. Competitive binding by (±) JQ1 displaces the BRD4 fusion oncoprotein from chromatin, prompting squamous differentiation and specific antiproliferative effects in BRD4-dependent cell lines and patient-derived xenograft models establishing proof-of-concept for targeting protein-protein interactions of epigenetic readers.1 Chiral version is available for purchase (Cat#10-1584).
• Uses: rac-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 isomer 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. (±)-JQ1 has been used to study its effect on adipogenesis, by analysing the its impact on the regulation of genes involved in this process especially peroxisome proliferator-activated receptor (PPAR-g), the CCAAT/enhancer-binding protein (C/EBPa) and, STAT5A and B. JQ1 has been used in drug binding assays as a chemical inhibitor of BRD4 to study the CRBN′s substrate recruiting function in mouse and human.

Technology Process of (±)-JQ1

There total 10 articles about (±)-JQ1 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

Trimethyl orthoacetate (1445-45-0) + tert-butyl 2-(5-(4-chlorophenyl)-6,7-dimethyl-2-thioxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-3-yl)acetate (1268524-68-0) → [4-(4-chlorophenyl)-2,3,9-trimethyl-6H-1-thia-5,7,8,9a-tetraazacyclopenta[e]azulen-6-yl]acetic acid tert-butyl ester (1268524-69-1)

Guidance literature:

tert-butyl 2-(5-(4-chlorophenyl)-6,7-dimethyl-2-thioxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-3-yl)acetate; With hydrazine; In tetrahydrofuran; at 0 - 23 ℃; for 1h;

Trimethyl orthoacetate; In toluene; at 120 ℃; for 2h;

Reference yield:

Trimethyl orthoacetate (1445-45-0) + C21H25ClN4O2S → [4-(4-chlorophenyl)-2,3,9-trimethyl-6H-1-thia-5,7,8,9a-tetraazacyclopenta[e]azulen-6-yl]acetic acid tert-butyl ester (1268524-69-1)

Guidance literature:

In toluene; at 110 ℃;

DOI:10.1016/j.tetlet.2015.02.062

Reference yield:

C21H25ClN4O2S + acetic acid (64-19-7,77671-22-8) → [4-(4-chlorophenyl)-2,3,9-trimethyl-6H-1-thia-5,7,8,9a-tetraazacyclopenta[e]azulen-6-yl]acetic acid tert-butyl ester (1268524-69-1)

Guidance literature:

C₂₁H₂₅ClN₄O₂S; acetic acid; With 1-methyl-pyrrolidin-2-one; isobutyl chloroformate; In tetrahydrofuran; for 5h; Inert atmosphere; Cooling with ice;

In tetrahydrofuran; butan-1-ol; at 90 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.201307803

upstream raw materials:

Trimethyl orthoacetate

tert-butyl 2-(5-(4-chlorophenyl)-6,7-dimethyl-2-thioxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-3-yl)acetate

p-chlorobenzoylacetonitrile

acetic acid

Downstream raw materials:

[4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl]acetic acid

(-)-JQ₁

(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

(S)-[4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl]acetic acid