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3-Hydroxyisoindolin-1-one derivates: Synthesis by palladium-catalyzed C H activation as BRD4 inhibitors against human acute myeloid leukemia (AML) cells

Bioorganic Chemistry, ISSN: 0045-2068, Vol: 86, Page: 119-125
2019
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Bromodomain protein 4 (BRD4) is a member of the bromodomain and extra-terminal domain (BET) protein family, which plays a key role in transcriptional regulation. Recent biological and pharmacological studies have enabled linking of the BET bromodomains with diseases, including inflammation and cancer, suggesting that bromodomains are druggable targets. In this study, we made further structural modifications of our previously reported BRD4 inhibitors, to develop new chemical scaffold 3-Hydroxyisoindolin-1-One. Then a series of compounds ( 10a-q ) were synthesized via palladium-catalyzed C H activation and BRD4-inhibitory activities and anti-proliferative effects of these compounds were evaluated. Compound 10e exhibited excellent BRD4-inhibitory activity with IC 50 value of 80 nM and anti-proliferation potency with IC 50 value of 365 nM in HL-60 (human promyelocytic leukemia) cancer cell lines. We have demonstrated compound 10e modulated the intrinsic apoptotic pathway. In conclusion, these results suggested that compound 10e could be utilized as a BRD4 inhibitor for further leukemia treatment.

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