Estradiol dimers as a new class of steroid sulfatase reversible inhibitors

被引：14

作者：

Fournier, Diane

Poirier, Donald ^{[1
]}

机构：

[1] CHUQ CHUL Res Ctr, Div Med Chem, Oncol & Mol Endocrinol Lab, Quebec City, PQ G1V 4G2, Canada

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 03期

基金：

加拿大健康研究院;

关键词：

Sulfatase; Steroid; Inhibitor; Dimer; Enzyme; Cancer; ESTRONE SULFATASE; BREAST-CANCER; MODULATORS; ENZYMES; TISSUE;

D O I：

10.1016/j.bmcl.2008.12.047

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of estradiol dimers was synthesized or selected from compounds available in our laboratory and tested for inhibition against steroid sulfatase. Dimers linked by their C17 position, compounds 7 and 8, showed inhibitory potency similar (56% and 54% at 1 mu M) to that of our best previously reported reversible inhibitor EM-690 (62% at 1 mu M). Docking experiment seems to indicate that C17-C17 dimers bind in a similar way to EM-690 whereas C16-O3 and C16-C16 dimers bind in an upside-down position. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：693 / 696

页数：4

共 50 条

[31] Design, synthesis, and biological evaluation of new arylamide derivatives possessing sulfonate or sulfamate moieties as steroid sulfatase enzyme inhibitors
El-Gamal, Mohammed I.
Semreen, Mohammad H.
Foster, Paul A.
Potter, Barry V. L.
BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (12) : 2762 - 2767
[32] Synthesis, Biological Evaluation and the Rationalisation of the Inhibitory Activity of a Range of Sulfonate Derivatives of Estrone (E1) in the Design of Reversible Inhibitors of Estrone Sulfatase (ES)
Akbarzadeh, Mohsen
Cartledge, Timothy
Ahmed, Sabbir
LETTERS IN DRUG DESIGN & DISCOVERY, 2014, 11 (08) : 985 - 992
[33] Design and synthesis of 3-benzylaminocoumarin-7-O-sulfamate derivatives as steroid sulfatase inhibitors
Hng, Yue
Lin, Mei-Hsiang
Lin, Tzung-Sheng
Liu, I-Chen
Lin, I-Chun
Lu, Yeh-Lin
Chang, Chiao-Nien
Chiu, Pei-Fang
Tsai, Keng-Chang
Chen, Mei-Jou
Liang, Pi-Hui
BIOORGANIC CHEMISTRY, 2020, 96
[34] Multiple Pathways for the Irreversible Inhibition of Steroid Sulfatase with Quinone Methide-Generating Suicide Inhibitors
Ahmed, Vanessa
Liu, Yong
Taylor, Scott D.
CHEMBIOCHEM, 2009, 10 (09) : 1457 - 1461
[35] Highly Potent First Examples of Dual Aromatase-Steroid Sulfatase Inhibitors based on a Biphenyl Template
Woo, L. W. Lawrence
Jackson, Toby
Putey, Aurelien
Cozier, Gyles
Leonard, Phililp
Acharya, K. Ravi
Chander, Surinder K.
Purohit, Atul
Reed, Michael J.
Potter, Barry V. L.
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (05) : 2155 - 2170
[36] Structure-Activity Relationship for the First-in-Class Clinical Steroid Sulfatase Inhibitor Irosustat (STX64, BN83495)
Woo, L. W. Lawrence
Ganeshapillai, Dharshini
Thomas, Mark P.
Sutcliffe, Oliver B.
Malini, Bindu
Mahon, Mary F.
Purohit, Atul
Potter, Barry V. L.
CHEMMEDCHEM, 2011, 6 (11) : 2019 - 2034
[37] Design and synthesis of silicon-containing steroid sulfatase inhibitors possessing pro-estrogen antagonistic character
Kajita, Daisuke
Nakamura, Masaharu
Matsumoto, Yotaro
Makishima, Makoto
Hashimoto, Yuichi
BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (07) : 2244 - 2252
[38] C-3- and C-4-Substituted Bicyclic Coumarin Sulfamates as Potent Steroid Sulfatase Inhibitors
Ganeshapillai, Dharshini
Woo, L. W. Lawrence
Thomas, Mark P.
Purohit, Atul
Potter, Barry V. L.
ACS OMEGA, 2018, 3 (09): : 10748 - 10772
[39] Synthesis and Biological Evaluation of Fluorinated 3-Phenylcoumarin-7-O-Sulfamate Derivatives as Steroid Sulfatase Inhibitors
Demkowicz, Sebastian
Dasko, Mateusz
Kozak, Witold
Krawczyk, Katarzyna
Witt, Dariusz
Maslyk, Maciej
Kubinski, Konrad
Rachon, Janusz
CHEMICAL BIOLOGY & DRUG DESIGN, 2016, 87 (02) : 233 - 238
[40] An efficient steroid pharmacophore-based strategy to identify new aromatase inhibitors
Neves, Marco A. C.
Dinis, Teresa C. P.
Colombo, Giorgio
Sa e Melo, M. Luisa
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (10) : 4121 - 4127

← 1 2 3 4 5 →