Structural Factors Affecting Cytotoxic Activity of (E)-1-(Benzo[d][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-one Derivatives

被引：12

作者：

Konieczny, Marek T. ^{[1
]}

Bulakowska, Anita ^{[2
]}

Polak, Justyna ^{[2
]}

Pirska, Danuta ^{[2
]}

Konieczny, Wojciech ^{[2
]}

Gryn, Patrycja ^{[2
]}

Skladanowski, Andrzej ^{[3
]}

Sabisz, Michal ^{[3
]}

Lemke, Krzysztof ^{[4
]}

Pieczykolan, Anna ^{[4
]}

Galazka, Marlena ^{[4
]}

Wiciejowska, Katarzyna ^{[4
]}

Wietrzyk, Joanna ^{[5
]}

机构：

[1] Med Univ Gdansk, Dept Chem Technol Drugs, PL-80416 Gdansk, Poland

[2] Med Univ Gdansk, Dept Organ Chem, PL-80416 Gdansk, Poland

[3] Gdansk Univ Technol, Dept Pharmaceut Technol & Biochem, PL-80233 Gdansk, Poland

[4] Adamed Ltd, Drug Discovery Dept, Czosnow, Poland

[5] Polish Acad Sci, Inst Immunol & Expt Therapy, Dept Expt Oncol, PL-53114 Wroclaw, Poland

来源：

CHEMICAL BIOLOGY & DRUG DESIGN | 2014年 / 84卷 / 01期

关键词：

benzoxathiole; chalcone; cytotoxic activity; SAR; structure optimization; ANTIMITOTIC CHALCONES;

D O I：

10.1111/cbdd.12296

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Derivatives of (E)-1-(5-alkoxybenzo[d][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-one 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.

引用

页码：86 / 91

页数：6

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