(+)-JQ1 (free acid) Synthesis Route

(+)-JQ1 (free acid) Synthesis

(+)-JQ1 (free acid) (Synonyms: (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)

(+)-JQ1 (free acid) is an inhibitor of bromodomain and extra terminal domain (BET) family proteins (Kds = 128, 59.5, 49.0, and 190 nM for JQ1 binding to bromodomains of BRD2, BRD3, BRD4, and BRDT, respectively), blocking their interaction with acetylated histones.1,2 Enantiomerically pure (+)-JQ1 (Item No. 11187) binds to BRD4 bromodomains 1 and 2 with Kd values of ~50 and 90 nM, respectively, whereas the (−)-JQ1 (Item No. 11232) stereoisomer has no appreciable affinity to BET bromodomains.1 JQ1 has been used as a chemical probe to investigate the role of BET bromodomains in the transcriptional regulation of oncogenesis.

(+)-JQ1 (free acid)

A selective inhibitor of BET bromodomains

Item No. AB03888
CAS No. 202592-23-2
Purity: 95%

1mg

＄12.00

5mg

＄18.00

100mg

＄74.00

250mg

＄114.00

＄153.00

＄495.00

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(+)-JQ1 (free acid) Synthetic Route

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AB03888

CAS: 202592-23-2

1.1: copper chloride (II); potassium hydroxide; oxygen/N,N-dimethyl acetamide/12 h/25 °C
2.1: morpholine; sulphur / ethanol / 12 h / 25 °C
3.1:N,N,N′,N′-tetramethyl-O-(6-chloro-1H-benzotriazol-1-yl)uranium hexafluorophosphate; N-ethyl-N,N-diisopropylamine /N,N-dimethyl-formamide / 0.08 h / 23 °C
3.2: 16 h / 23 °C
4.1: piperidine / N,N-dimethyl-formamide / 0.5 h / 23 °C
5.1: glacial acetic acid / ethanol / 0.5 h / 85 °C
6.1: phosphorous pentasulfide; Sodium hydrogenocarbonate/tetrahydrofuran/16 h/ 90°C
7.1: hydrazine hydrate monohydrate / tetrahydrofuran / 1 h / 23 °C
7.2: 2 h / 120 °C
8.1: trifluoroacetic acid / 2 h / 20 °C.

Order (+)-JQ1 (free acid) Intermediates

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References

1.Current Patent Assignee: CSPC ZHONGQI PHARMACEUTICAL TECHNOLOGY - EP3686204, 2020, A1. 

2.Filippakopoulos, P., Qi, J., Picaud, S., et al. Selective inhibition of BET bromodomains. Nature 468(7327), 1067-1073 (2010).

3.Dawson, M.A., Kouzarides, T., and Huntly, B.J. Targeting epigenetic readers in cancer. N. Engl. J. Med. 367(7), 647-657 (2012).

4.Delmore, J.E., Issa, G.C., Lemieux, M.E., et al. BET bromodomain inhibition as a therapeutic strategy to target c-Myc. Cell 146(6), 904-917 (2011).

5.Mertz, J.A., Conery, A.R., Bryant, B.M., et al. Targeting MYC dependence in cancer by inhibiting BET bromodomains. Proc. Natl. Acad. Sci. USA 108(40), 16669-16674 (2011).

6.Dawson, M.A., Prinjha, R.K., Dittmann, A., et al. Inhibition of BET recruitment to chromatin as an effective treatment for MLL-fusion leukaemia. Nature 478(7370), 529-533 (2011).