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ChemicalBook >> CAS DataBase List >>(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)-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)-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
(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 structure
CAS No.
1268524-70-4
Chemical Name:
(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
Synonyms
tert-butyl (S)-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;(+)-JQ1;(+)-JQ-1;jq01;S-JQ1;CS-799;(+)JQ1;JQ1 compound;(+)-JQ1, >=99%;3,9-trimethyl-6
CBNumber:
CB72572988
Molecular Formula:
C23H25ClN4O2S
Molecular Weight:
456.99
MDL Number:
MFCD22683748
MOL File:
1268524-70-4.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59
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(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 Properties

Melting point >205°C (dec.)
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
Stability Stable for 1 year as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.
InChIKey DNVXATUJJDPFDM-KRWDZBQOSA-N
FDA UNII 1MRH0IMX0W

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H332-H335
Precautionary statements  P261-P280-P305+P351+P338

(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 price More Price(44)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML1524 (+)-JQ1 ≥98% (HPLC) 1268524-70-4 5mg $196 2024-03-01 Buy
Sigma-Aldrich SML1524 (+)-JQ1 ≥98% (HPLC) 1268524-70-4 25mg $711 2024-03-01 Buy
Cayman Chemical 11187 (+)-JQ1 ≥98% 1268524-70-4 1mg $28 2024-03-01 Buy
Cayman Chemical 11187 (+)-JQ1 ≥98% 1268524-70-4 5mg $98 2024-03-01 Buy
Cayman Chemical 11187 (+)-JQ1 ≥98% 1268524-70-4 10mg $140 2024-03-01 Buy
Product number Packaging Price Buy
SML1524 5mg $196 Buy
SML1524 25mg $711 Buy
11187 1mg $28 Buy
11187 5mg $98 Buy
11187 10mg $140 Buy

(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 Chemical Properties,Uses,Production

Biological Activity

(+)-JQ1 is a BET bromodomain inhibitor that acts on BRD4 (2) with C50 being 33nM. Except the BET family, (+)-JQ1 does not bind to the Bromodomain structure domain of other family.

In vitro

(+)-JQ1 enantiomer can bind to directly the Kac binding site of BET bromodomain structure domain. (+)-JQ1 (500nM) and chromatin competitively bind to BRD4, leading to NMC cell differentiation and growth standstill. The Ki67 staining decrease proves that  (+)-JQ1(500nM) weakens the rapid proliferation of NMC 797 and Per403 cell system.      (+)-JQ1(500nM) acts on NMC 797 cells, effectively reducing the expression of BRD4 target gene. (+)-JQ1acts on NMC11060 cells inhibiting cell activity with IC50 being 4nM. (+)-JQ1 acts on MM cell system and strongly inhibits MYC expression. (+)-JQ1 inhibits the proliferation of KMS-34 and LR5 with IC50 being 68nM and 98nM respectively. After being treated by  (+)-JQ1(500nM), the proportion of MM.1S cell in S phase decrease and more cells stasis in the G0/G1 phase.
(+)-JQ1(500nM) dyed by β-galactosidase results in significant cell senescence. In the CD138+-derived MM sample treated by (+)-JQ1(800nM), the cell activity significantly decrease. (+)-JQ1 inhibits LP-1 cell growth with GI50 being 98nM. (+)-JQ1 (625nM) resulted in an increase in the proportion of LP-1 cells at G0/G1 phase. (+)-JQ1 (500nM) acts on LP-1 cells inhibiting MYC, BRD4 and CDK9 expression. (+)-JQ1 (1 μM) deals with latent infection of Jurkat T cells and activates HIV transcription. (+)-JQ1 (50μM) acts on Jurkat and HeLa cells, primarily stimulating Tat-dependent HIV transcription. (+)-JQ1 (5 μM) acts on J-Lat A2 cell inducing Brd4 dissociation, allowing Tat to recruit SEC to the HIV promoter and inducing Pol II CTD phosphorylation and viral transcription.

In vivo

(+)-JQ1(50mg /kg) treats mice with NMC797 transplanted tumors inhibiting tumor growth. (+)-JQ1(50mg/kg) erases NUT nuclear spots in mice with NMC797 transplanted tumors, consistent with competitive binding to nuclear chromatin. (+)-JQ1 (50mg/kg) treats NMC797 transplanted tumor, significantly inducing (31grade) keratin expression. (+)-JQ1(50mg/kg) treats mouse model carrying NMC transplanted tumor, promoting differentiation, tumor decline and prolonging life. (+)-JQ1(50mg/kg) treats MM.1S-luc+ cells through intravenous injection. Compared with animals in control group, the life of SCID beige mice carrying orthotopic transplanted tumors significantly extends. Through intraperitoneal injection (+)-JQ1(50mg/kg) can prolong the life of mice carrying Raji xenograft greatly.

Characteristic

(+)-JQ1 is more effective than (-)-JQ1.

Description

JQ1 (+) (1268524-70-4) is a potent BET bromodomain inhibitor and is the active isomer.?? 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 (data for + isomer).1 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.1?Induces squamous differentiation in NMC cell lines and inhibits tumor growth in NMC xenografts.2?Displays reversible contraceptive effects in male mice.3?Blocks inflammation and bone loss in periodontitis.4?Reverses CAR T cell extinction.5

Uses

(+)-JQ1 has been used in flow cytometry assay, cell viability assay and quantitative PCR assay in order to investigate on the reversal of HIV-1 latency.

Uses

BET bromodomain inhibitor JQ1 activates HIV latency through antagonizing Brd4 inhibition of Tat-transactivation.

Definition

ChEBI: JQ1 is a member of the class of thienotriazolodiazepines that is the tert-butyl ester of [(6S)-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. An inhibitor of bromodomain-containing protein 4 that exhibits anti-cancer and cardioprotective properties. It has a role as a bromodomain-containing protein 4 inhibitor, a cardioprotective agent, an antineoplastic agent, an anti-inflammatory agent, an angiogenesis inhibitor, an apoptosis inducer and a ferroptosis inducer. It is a thienotriazolodiazepine, an organochlorine compound, a carboxylic ester 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. 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.

Biochem/physiol Actions

(+)-JQ1 is a high affinity, potent and selective inhibitor of BET bromodomain proteins, including BRD2, BRD3, BRD4 and BRDT. (+)-JQ1 (also known as SGCBD01), the active enantiomer of (+/-)-JQ1, inhibits Brd4 (bromodomain-containing 4), which forms complexes with chromatin via two tandem bromodomains (BD1 and BD2) that bind to acetylated lysine residues in histones and Brd4 association with acetylated chromatin is believed to regulate the recruitment of elongation factor b and additional transcription factors to specific promoter regions. The nuclear protein in testis (NUT) gene is known to form fusions with Brd4 that create a potent oncogene, leading to rare, but highly lethal tumors referred to as NUT midline carcinomas (NMC). (+)-JQ1 inhibits recruitment and binding of Brd4 to TNFa and E-selectin promoter elements, and accelerates recovery time in FRAP (fluorescence recovery after photobleaching) assays using GFP-Brd4. Thus (+)-JQ1 is a useful tool to study the role of Brd4 in transcriptional initiation.For characterization details of (+)-JQ1, please visit the JQ-1 probe summary on the Structural Genomics Consortium (SGC) website.(-)-JQ1 is the negative control for the active enantiomer, (+)-JQ1. (-)-JQ1 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

-20°C

References

References/Citations:

(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 synthesis

1268524-67-9
1068-57-1
1268524-70-4
Synthesis 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 from 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)- and Acethydrazide

(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 Preparation Products And Raw materials

Raw materials

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)- 4-CHLOROBENZOYLACETONITRILE Butanoic acid, 3-aMino-4-[[3-(4-chlorobenzoyl)-4,5-diMethyl-2-thienyl]aMino]-4-oxo-, 1,1-diMethylethyl ester, (3S)- 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)- 2-AMino-3-(p-chlorobenzoyl)-4,5-diMethylthiophene
Trimethyl orthoacetate

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Preparation Products

(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

(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 Suppliers

Global( 234)Suppliers
Supplier Tel Email Country ProdList Advantage
Capot Chemical Co.,Ltd. 		571-85586718 +8613336195806 sales@capotchem.com China 29797 60
Nanjing ChemLin Chemical Industry Co., Ltd. 		025-83697070 product@chemlin.com.cn CHINA 3012 60
ATK CHEMICAL COMPANY LIMITED 		+undefined-21-51877795 ivan@atkchemical.com China 32480 60
career henan chemical co 		+86-0371-86658258 sales@coreychem.com China 29914 58
Zhejiang ZETian Fine Chemicals Co. LTD 		18957127338 stella@zetchem.com China 2141 58
Biochempartner 		0086-13720134139 candy@biochempartner.com CHINA 967 58
Jilin Chinese Academy of Sciences - Yanshen Technology Co., Ltd. 		0431-80514535 13634302652 Extension@chemextension.com CHINA 967 58
Hubei Jusheng Technology Co.,Ltd. 		18871490254 linda@hubeijusheng.com CHINA 28180 58
Accela ChemBio Inc. 		(+1)-858-699-3322 info@accelachem.com United States 19965 58
Shandong chuangyingchemical Co., Ltd. 		18853181302 sale@chuangyingchem.com CHINA 5909 58
Supplier Advantage
Capot Chemical Co.,Ltd. 		60
Nanjing ChemLin Chemical Industry Co., Ltd. 		60
ATK CHEMICAL COMPANY LIMITED 		60
career henan chemical co 		58
Zhejiang ZETian Fine Chemicals Co. LTD 		58
Biochempartner 		58
Jilin Chinese Academy of Sciences - Yanshen Technology Co., Ltd. 		58
Hubei Jusheng Technology Co.,Ltd. 		58
Accela ChemBio Inc. 		58
Shandong chuangyingchemical Co., Ltd. 		58

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View Lastest Price from (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 manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
(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 pictures 2020-03-06 (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
12688524-70-4
 US $1.00 / KG 1KG 97%-99.9% 200kg Career Henan Chemical Co
(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 pictures 2020-01-14 (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
1268524-70-4
 US $7.00 / KG 1KG 99% 100KG Career Henan Chemical Co
(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 pictures 2019-07-06 (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
1268524-70-4
 US $1.00 / KG 1G 98% 100KG Career Henan Chemical Co

(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 Spectrum

(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(1268524-70-4)1HNMR

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)Related Search:

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(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)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-triMethyl-6H-thienol[3,2-f][1,2,4]troazolo[4,3-a][1,4]diazepin-6-yl)acetate[(+)-6] (+)-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 (+)-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 CAS： BroModoMain Inhibitor, (+)-JQ1 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, (6S)- (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 (+)-JQ-1 (6s)-6-(2-Tert-butoxy-2-oxoethyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6,7-dihydrothieno[3,2-F][1,2,4]triazolo[4,3-A][1,4]diazepin-10-ium jq01 (S)-tert-Butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno-[3,2-f][1,2,4]triazolo[4,3-a][1 (+)-JQ1, >=99% CS-799 (6S)-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 JQ-1;JQ 1;JQ1;+JQ 1;+JQ-1;+JQ1 S-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]diaz 3,9-trimethyl-6 (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 (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 USP/EP/BP Bet bromodomain inhibitors (S)-tert-butyl 2-(4-(4-chlorophenyl)-2 4]diazepin-6-yl)acetate 9-triMethyl-6H-thieno[3 tert-butyl 2-((6S)-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 (6s)-6-(2-Tert-butoxy-2-oxoethyl)-4-(4-chlorophenyl)-2,3,9-t... (+)-JQ-1 tert-butyl (S)-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 (+)-JQ1 Ceftobiprole Impurity 23 (+)JQ1 JQ1 compound Bromodomain Inhibitor 1268524-70-4 12688524-70-4 Inhibitors Epigenetics Apis