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Abstract
Based on the frameworks of 7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one, 3-hydroxy- 7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one and 3-hydroxy-8,9,10,11-tetrahydro-7H-cyclohepta[c] chromen-6-one, a series of bicoumarin thiophosphate analogs have been synthesized and biologically evaluated. Additionally, their binding modes have been modeled using docking techniques. The inhibitory properties of the synthesized compounds were tested against the STS isolated from human placenta. Most of the new STS inhibitors possessed good activities against STS. In particular, we found that the bis- (6-oxo-7,8,9,10-tetrahydro-6H-benzo[c]chromen-3-yl) hydrogenthiophosphate (10b) produced the largest inhibitory effect, with an IC50 value of 860 nM (an IC50 value of 1 mM for the 665-COUMATE used as a reference). The structure-activity relationships of the synthesized bicoumarin thiophosphate derivatives toward the STS enzyme have been discussed previously.
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Authors (6)
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Maciej Masłyk
- The John Paul II Catholic University of Lublin Department of Molecular Biology, Faculty of Biotechnology and Environment Sciences
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Bartłomiej Gielniewski
- The John Paul II Catholic University of Lublin Department of Molecular Biology, Faculty of Biotechnology and Environment Sciences
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Details
- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
no. 101,
pages 358 - 366,
ISSN: 0223-5234 - Language:
- English
- Publication year:
- 2015
- Bibliographic description:
- Demkowicz S., Kozak W., Daśko M., Masłyk M., Gielniewski B., Rachoń J.: Synthesis of bicoumarin thiophosphate derivatives as steroid sulfatase inhibitors// EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. -Vol. 101, (2015), s.358-366
- DOI:
- Digital Object Identifier (open in new tab) 10.1016/j.ejmech.2015.06.051
- Verified by:
- Gdańsk University of Technology
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