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Synthesis and Steroid Sulfatase Inhibitory Effect of Androstane-3β-O-sulfonate and -sulfamate Derivatives
YAKHAK HOEJI 2018;62(6):401-409
Published online December 30, 2018
© 2018 The Pharmaceutical Society of Korea.

Ji-Hyun Park and Eunsook Ma*

College of Pharmacy, Daegu Catholic University, 13-13 Hayang-ro Gyeongsan-si, 38430, Korea
Correspondence to: Eunsook Ma College of Pharmacy, Daegu Catholic University, 13-13 Hayang-ro Gyeongsan-si, 38430, Korea Tel: +82-53-850-3621 Fax: +82-53-850-3602 E-mail: masook@cu.ac.kr
Received October 10, 2018; Revised December 3, 2018; Accepted December 3, 2018.
Abstract
The development of potent steroid sulfatase inhibitors is an important new therapeutic strategy for the treatment of postmenopausal women with breast cancer. In postmenopausal breast cancer, the desulfation of dehydroepiandrostene sulfate (DHEAS) by steroid sulfatase (STS) that takes place in peripheral tissues becomes as an important step in estrogen production. Androstane-3β-O-mesylsulfonate, -3β-O-tosylsulfonate, and -3β-O-sulfamate derivatives with substituents at positions 5 and 6 were synthesized using DHEA as the parent structure and STS inhibitory activity was measured at 3 μM in human Jeg-3 cells. 6β-Chloro-5α-hydroxyandrostane-3β-O-sulfamate (13) was found to be the most active compound with STS inhibition 71%.
Keywords : breast cancer, steroid sulfatase inhibitor, androstane-3β-O-sufonate, androstane-3β-O-sulfamate


June 2019, 63 (3)
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