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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
Author(s) -
Konieczny Marek T.,
Bułakowska Anita,
Polak Justyna,
Pirska Danuta,
Konieczny Wojciech,
Gryń Patrycja,
Skladanowski Andrzej,
Sabisz Michał,
Lemke Krzysztof,
Pieczykolan Anna,
Gałązka Marlena,
Wiciejowska Katarzyna,
Wietrzyk Joanna
Publication year - 2014
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12296
Subject(s) - cytotoxic t cell , stereochemistry , ring (chemistry) , chemistry , cytotoxicity , alkoxy group , structure–activity relationship , in vitro , biochemistry , organic chemistry , alkyl
Derivatives of ( E )‐1‐(5‐alkoxybenzo[ d ][1,3]oxathiol‐6‐yl)‐3‐phenylprop‐2‐en‐1‐one [1][Dimmock J.R., 1999] demonstrated exceptionally high in vitro cytotoxic activity, with IC 50 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.