1268524-69-1

Basic information

• Product Name: (±)-JQ1
• Synonyms: [(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;rac JQ-1;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
• CAS NO: 1268524-69-1
• Molecular Formula: C₂₃H₂₅ClN₄O₂S
• Molecular Weight: 456.9882
• Mol File: 1268524-69-1.mol

Chemical Properties

• Boiling Point: 610.4±65.0 °C(Predicted)
• Appearance: white to beige/
• Density: 1.33±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble2mg/mL, clear (warmed)
• PKA: 2.05±0.60(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.
• CAS DataBase Reference: (±)-JQ1(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-JQ1(1268524-69-1)
• EPA Substance Registry System: (±)-JQ1(1268524-69-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1268524-69-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(±)-JQ1 is used as a chemical inhibitor for studying the bromodomain and extraterminal (BET) proteins, specifically BRD2, BRD4, and CREBBP. Its competitive binding properties make it a valuable tool in understanding the role of these proteins in various cellular processes and their potential as therapeutic targets.
Used in Research Applications:
(±)-JQ1 is used as a research tool to study the effects of BRD4 inhibition on various cellular processes, such as squamous differentiation and antiproliferative effects in BRD4-dependent cell lines and patient-derived xenograft models.
Used in HIV Research:
(±)-JQ1 is used as a compound to study its ability to activate HIV latency by antagonizing Brd4 inhibition of Tat-transactivation, providing insights into potential therapeutic strategies for HIV treatment.
Used in Adipogenesis Research:
(±)-JQ1 is used to study its effect on adipogenesis, particularly its impact on the regulation of genes involved in this process, such as peroxisome proliferator-activated receptor (PPAR-g), the CCAAT/enhancer-binding protein (C/EBPa), and STAT5A and B.
Used in Drug Binding Assays:
(±)-JQ1 is used in drug binding assays to study the CRBN's substrate recruiting function in mouse and human cells, providing valuable information on the molecular mechanisms underlying its activity.

Biochem/physiol Actions

(±)-JQ1 is a Brd4 inhibitor. JQ1 is known to suppress cell proliferation and therefore, can be used as a therapeutic drug for a number of cancers including multiple myeloma and acute myeloid leukemia.

References

1) Filippakopoulos et al. (2010), Selective inhibition of BET bromodomains; Nature, 468 1067

Upstream product

• 1268524-65-7 (S)-tert-butyl 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-((3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)amino)-4-oxobutanoate 
• 1268524-67-9 tert-butyl (S)-2-(5-(4-chlorophenyl)-6,7-dimethyl-2-oxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-3-yl)acetate 
• 1268524-68-0 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 
• 1445-45-0 Trimethyl orthoacetate 
• 50508-66-2 (2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone 
• 64-19-7 acetic acid 
• 4640-66-8 p-chlorobenzoylacetonitrile 

Downstream Products

• 202592-28-7 [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 
• 1268524-71-5 (-)-JQ₁ 
• 1268524-70-4 (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 
• 202592-23-2 (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 

Relevant articles and documents

Scalable syntheses of the BET bromodomain inhibitor JQ1

We have developed methods involving the use of alternate, safer reagents for the scalable syntheses of the potent BET bromodomain inhibitor JQ1. A one-pot three step method, involving the conversion of a benzodiazepine to a thioamide using Lawesson's reagent, followed by amidrazone formation and installation of the triazole moiety furnished JQ1. This method provides good yields and a facile purification process. For the synthesis of enantiomerically enriched (+)-JQ1, the highly toxic reagent diethyl chlorophosphate, used in a previous synthesis, was replaced with the safer reagent diphenyl chlorophosphate in the three-step one-pot triazole formation without effecting yields and enantiomeric purity of (+)-JQ1.

Preparation of small-molecule microarrays by trans-cyclooctene tetrazine ligation and their application in the high-throughput screening of protein-protein interaction inhibitors of bromodomains

Fast and efficient: A library of trans-cyclooctene (TCO)-modified small molecules were immobilized on tetrazine-functionalized glass slides by using the fastest bioorthogonal reaction known. The resulting small-molecule microarray was screened against a variety of human bromodomains to identify protein-protein interaction inhibitors. Copyright

MALE CONTRACEPTIVE COMPOSITIONS AND METHODS OF USE

The invention relates to compositions and methods for effecting male contraception.