European Journal of Medicinal Chemistry, volume 128, pages 79-87

Synthesis and biological evaluation of fluorinated N -benzoyl and N -phenylacetoyl derivatives of 3-(4-aminophenyl)-coumarin-7- O -sulfamate as steroid sulfatase inhibitors

Mateusz Daśko ^{1, 2, 3, 4}

Maja Przybyłowska ^{1, 2, 3, 4}

Janusz Rachon ^{1, 2, 3, 4}

Maciej Masłyk ⁵

Konrad Kubiński ⁵

Majus Misiak ⁶

Andrzej Składanowski ⁶

Sebastian Demkowicz ^{1, 2, 3, 4}

Hide authors affiliations Show authors affiliations: 6 affiliations

Faculty of Chemistry

Gdansk University of Technology |

Narutowicza 11/12 80-233 Gdansk Poland |

⁴

Department of Organic Chemistry

⁵

Department of Molecular Biology Faculty of Biotechnology and Environment Sciences The John Paul II Catholic University of Lublin Konstantynów 1i 20‐708 Lublin Poland |

⁶

Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry , Gdańsk University of Technology , Narutowicza 11/12 , 80-233 Gdańsk , Poland. |

Publication type: Journal Article

Publication date: 2017-03-01

Elsevier

Journal: European Journal of Medicinal Chemistry

Quartile SCImago

Quartile WOS

Impact factor: 6.7

ISSN: 02235234, 17683254

DOI: 10.1016/j.ejmech.2017.01.028

Copy DOI

Organic Chemistry

Drug Discovery

General Medicine

Pharmacology

Abstract

In the present work, we report convenient methods for the synthesis of 3-(4-aminophenyl)-coumarin-7-O-sulfamate derivatives N-acylated with fluorinated analogues of benzoic or phenylacetic acid as steroid sulfatase (STS) inhibitors. The design of these potential STS inhibitors was supported by molecular modeling techniques. Additionally, computational docking methods were used to determine the binding modes of the synthesized inhibitors and to identify potential interactions between inhibitors and amino acid residues located in the active site of STS. The inhibitory effects of the synthesized compounds were tested on STS isolated from human placenta and against estrogen receptor-(ER)-positive MCF-7 and T47D cells, as well as ER-negative MDA-MB-231 and SkBr3 cancer cell lines. In the course of our investigation, compounds 6c and 6j demonstrated the highest inhibitory effect in enzymatic STS assays, both with IC50 values of 0.18 μM (the IC50 value of coumarin-7-O-sulfamate is 1.38 μM, used as a reference). Compound 6j exhibited the highest potency against the MCF-7 and T47D cell lines (15.9 μM and 8.7 μM, respectively). The GI50 values of tamoxifen (used as a reference) were 6.8; 10.6; 15.1; 12.5 μM against MCF-7, T47D, MDA-MB-231 and SkBr3 cancer cell lines, respectively. Despite the slightly lower activity of compounds 1 and 2 (both in enzymatic and cell-based experiments) compared to 6g and 6j, analogues 1 and 2 proved to selectively inhibit the growth of ER- and PR-positive cell lines.

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Top-30

Citations by journals

	1 2 3
European Journal of Medicinal Chemistry	European Journal of Medicinal Chemistry, 3, 13.04% European Journal of Medicinal Chemistry 3 publications, 13.04%
Molecules	Molecules, 2, 8.7% Molecules 2 publications, 8.7%
RSC Advances	RSC Advances, 2, 8.7% RSC Advances 2 publications, 8.7%
Journal of Enzyme Inhibition and Medicinal Chemistry	Journal of Enzyme Inhibition and Medicinal Chemistry, 2, 8.7% Journal of Enzyme Inhibition and Medicinal Chemistry 2 publications, 8.7%
Current Topics in Medicinal Chemistry	Current Topics in Medicinal Chemistry, 1, 4.35% Current Topics in Medicinal Chemistry 1 publication, 4.35%
Current Organic Chemistry	Current Organic Chemistry, 1, 4.35% Current Organic Chemistry 1 publication, 4.35%
Applied Microbiology and Biotechnology	Applied Microbiology and Biotechnology, 1, 4.35% Applied Microbiology and Biotechnology 1 publication, 4.35%
Bioorganic Chemistry	Bioorganic Chemistry, 1, 4.35% Bioorganic Chemistry 1 publication, 4.35%
Bioorganic and Medicinal Chemistry	Bioorganic and Medicinal Chemistry, 1, 4.35% Bioorganic and Medicinal Chemistry 1 publication, 4.35%
Journal of Photochemistry and Photobiology A: Chemistry	Journal of Photochemistry and Photobiology A: Chemistry, 1, 4.35% Journal of Photochemistry and Photobiology A: Chemistry 1 publication, 4.35%
Drug Development Research	Drug Development Research, 1, 4.35% Drug Development Research 1 publication, 4.35%
Journal of Medicinal Chemistry	Journal of Medicinal Chemistry, 1, 4.35% Journal of Medicinal Chemistry 1 publication, 4.35%
Journal of Asian Natural Products Research	Journal of Asian Natural Products Research, 1, 4.35% Journal of Asian Natural Products Research 1 publication, 4.35%
Expert Opinion on Therapeutic Patents	Expert Opinion on Therapeutic Patents, 1, 4.35% Expert Opinion on Therapeutic Patents 1 publication, 4.35%
RSC Medicinal Chemistry	RSC Medicinal Chemistry, 1, 4.35% RSC Medicinal Chemistry 1 publication, 4.35%
Biomedicines	Biomedicines, 1, 4.35% Biomedicines 1 publication, 4.35%
Russian Chemical Reviews	Russian Chemical Reviews, 1, 4.35% Russian Chemical Reviews 1 publication, 4.35%
	1 2 3

Citations by publishers

	1 2 3 4 5 6
Elsevier	Elsevier, 6, 26.09% Elsevier 6 publications, 26.09%
Taylor & Francis	Taylor & Francis, 4, 17.39% Taylor & Francis 4 publications, 17.39%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 3, 13.04% Multidisciplinary Digital Publishing Institute (MDPI) 3 publications, 13.04%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 3, 13.04% Royal Society of Chemistry (RSC) 3 publications, 13.04%
Bentham Science	Bentham Science, 2, 8.7% Bentham Science 2 publications, 8.7%
Springer Nature	Springer Nature, 1, 4.35% Springer Nature 1 publication, 4.35%
Wiley	Wiley, 1, 4.35% Wiley 1 publication, 4.35%
American Chemical Society (ACS)	American Chemical Society (ACS), 1, 4.35% American Chemical Society (ACS) 1 publication, 4.35%
OAE Publishing Inc.	OAE Publishing Inc., 1, 4.35% OAE Publishing Inc. 1 publication, 4.35%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 4.35% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 4.35%
	1 2 3 4 5 6

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Daśko M. et al. Synthesis and biological evaluation of fluorinated N -benzoyl and N -phenylacetoyl derivatives of 3-(4-aminophenyl)-coumarin-7- O -sulfamate as steroid sulfatase inhibitors // European Journal of Medicinal Chemistry. 2017. Vol. 128. pp. 79-87.

GOST all authors (up to 50) Copy

Daśko M., Przybyłowska M., Rachon J., Masłyk M., Kubiński K., Misiak M., Składanowski A., Demkowicz S. Synthesis and biological evaluation of fluorinated N -benzoyl and N -phenylacetoyl derivatives of 3-(4-aminophenyl)-coumarin-7- O -sulfamate as steroid sulfatase inhibitors // European Journal of Medicinal Chemistry. 2017. Vol. 128. pp. 79-87.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.ejmech.2017.01.028

UR - https://doi.org/10.1016/j.ejmech.2017.01.028

TI - Synthesis and biological evaluation of fluorinated N -benzoyl and N -phenylacetoyl derivatives of 3-(4-aminophenyl)-coumarin-7- O -sulfamate as steroid sulfatase inhibitors

T2 - European Journal of Medicinal Chemistry

AU - Daśko, Mateusz

AU - Przybyłowska, Maja

AU - Rachon, Janusz

AU - Masłyk, Maciej

AU - Kubiński, Konrad

AU - Misiak, Majus

AU - Składanowski, Andrzej

AU - Demkowicz, Sebastian

PY - 2017

DA - 2017/03/01 00:00:00

PB - Elsevier

SP - 79-87

VL - 128

SN - 0223-5234

SN - 1768-3254

ER -

BibTex

Cite this

BibTex Copy

@article{2017_Daśko,

author = {Mateusz Daśko and Maja Przybyłowska and Janusz Rachon and Maciej Masłyk and Konrad Kubiński and Majus Misiak and Andrzej Składanowski and Sebastian Demkowicz},

title = {Synthesis and biological evaluation of fluorinated N -benzoyl and N -phenylacetoyl derivatives of 3-(4-aminophenyl)-coumarin-7- O -sulfamate as steroid sulfatase inhibitors},

journal = {European Journal of Medicinal Chemistry},

year = {2017},

volume = {128},

publisher = {Elsevier},

month = {mar},

url = {https://doi.org/10.1016/j.ejmech.2017.01.028},

pages = {79--87},

doi = {10.1016/j.ejmech.2017.01.028}

}

Found error?

Publisher

Elsevier

Journal

European Journal of Medicinal Chemistry

Quartile SCImago

Quartile WOS

Impact factor

6.7

ISSN

02235234 (Print)
17683254 (Electronic)