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Structural Factors Affecting Cytotoxic Activity of (E)-1-(Benzo[d ][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-one Derivatives
Abstract
Derivatives of (E)-1-(5-alkoxybenzo[d][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-one (1) demonstrated exceptionally high in vitro cytotoxic activity, with IC50 values of the most active derivatives in the nanomolar range. To identify structural fragments necessary for the activity, several analogs deprived of selected fragments were prepared, and their cytotoxic activity was tested. It was found that the activity depends on combined effects of (i) the heterocyclic ring, (ii) the alkoxy group at position 5 of the benzoxathiole ring, and (iii) the substituents in the phenyl ring B. Replacement of the sulfur atom by oxygen does not influence the activity. None of the listed structural fragments alone assured high cytotoxic activity.
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Authors (13)
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Marek T. Konieczny
- Medical University of Gdansk Department of Chemical Technology of Drugs
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Anita Bułakowska
- Medical University of Gdansk Department of Organic Chemistry
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Justyna Polak
- Medical University of Gdansk Department of Organic Chemistry
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Danuta Pirska
- Medical University of Gdansk Department of Organic Chemistry
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Wojciech Konieczny
- Medical University of Gdansk Department of Organic Chemistry
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Patrycja Gryń
- Medical University of Gdansk Department of Organic Chemistry
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Krzysztof Lemke
- Drug Discovery Department, Adamed Ltd. .
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Anna Pieczykolan
- Drug Discovery Department, Adamed Ltd. .
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Marlena Gałązka
- Drug Discovery Department, Adamed Ltd. .
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Katarzyna Wiciejowska
- Drug Discovery Department, Adamed Ltd. .
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Joanna Wietrzyk
- Institute of Immunology and Experimental Therapy .
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Details
- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
Chemical Biology & Drug Design
no. 84,
edition 1,
pages 86 - 91,
ISSN: 1747-0277 - Language:
- English
- Publication year:
- 2014
- Bibliographic description:
- Konieczny M., Bułakowska A., Polak J., Pirska D., Konieczny W., Gryń P., Składanowski A., Sabisz M., Lemke k., Pieczykolan A., Gałązka M., Wiciejowska K., Wietrzyk j.: Structural Factors Affecting Cytotoxic Activity of (E)-1-(Benzo[d ][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-one Derivatives// Chemical Biology & Drug Design. -Vol. 84, iss. 1 (2014), s.86-91
- DOI:
- Digital Object Identifier (open in new tab) 10.1111/cbdd.12296
- Verified by:
- Gdańsk University of Technology
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