Work

Heck- and Suzuki-coupling approaches to novel hydroquinone inhibitors of calcium ATPase

Year: 2019

Type: article

Abstract: In this study, we explored Heck- and Suzuki-coupling methodology to modify the template 2,5-di-tert-butylhydroquinone (BHQ, 2), an inhibitor of the enzyme sarco/endoplasmic reticulum calcium ATPase (SERCA). We found that by utilizing Suzuki coupling, we could successfully attach a six-carbon tether to BHQ that terminated in a leucine moiety to obtain target 14. Similar to related compounds based on the structure of the natural product thapsigargin, 14 displayed inhibitory potency against SERCA activity. This makes 14 a suitable candidate for the future attachment of a deactivating peptide to convey specificity for prostate cancer cells.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.15.94

Authors: Robert J Kempton, Taylor A Kidd-Kautz, Soizic Laurenceau, Stefan Paula

Institutions: Northern Kentucky University, Purdue University West Lafayette

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Northern Kentucky University, National Institutes of Health, National Institute of General Medical Sciences

Awards: IDeA Networks of Biomedical Research Excellence in Kentucky, Hydroquinone derivatives as novel calcium ATPase inhibitors