Design and synthesis of 3-benzylaminocoumarin-7-O-sulfamate derivatives as steroid sulfatase inhibitors

Yue Hng, Mei Hsiang Lin, Tzung Sheng Lin, I. Chen Liu, I. Chun Lin, Yeh Lin Lu, Chiao Nien Chang, Pei Fang Chiu, Keng Chang Tsai, Mei Jou Chen, Pi Hui Liang

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8 Citations (Scopus)


Steroid sulfatase (STS) is a sulfatase enzyme that catalyzes the conversion of sulfated steroid precursors to free steroid. The inhibition of STS could abate estrogenic steroids that stimulate the proliferation and development of breast cancer, and therefore STS is a potential target for adjuvant endocrine therapy. In this study, a series of 3-benzylaminocoumarin-7-O-sulfamate derivatives targeting STS were designed and synthesized. Structure-relationship activities (SAR) analysis revealed that attachment of a benzylamino group at the 3-position of coumarin improved inhibitory activity. Compound 3j was found to have the highest inhibition activity against human placenta isolated STS (IC50 0.13 μM) and MCF-7 cell lines (IC50 1.35 µM). Kinetic studies found compound 3j to be an irreversible inhibitor of STS, with KI and kinact value of 86.9 nM and 158.7 min−1, respectively.

Original languageEnglish
Article number103618
JournalBioorganic Chemistry
Publication statusPublished - Mar 2020


  • Breast cancer
  • Coumarin
  • Hormone dependent cancer
  • Irreversible inhibitors
  • Steroid sulfatase
  • Sulfamate

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry


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