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Efficient Synthesis and Cytotoxic Activity of Some Symmetrical Disulfides Derived from the Quinolin‐4(1 H )‐one Skeleton
Author(s) -
Soural Miroslav,
Hlaváč Jan,
Hradil Pavel,
Hajdúch Marián
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900428
Subject(s) - chemistry , trifluoroacetic acid , phenacyl , cytotoxicity , ring (chemistry) , cancer cell lines , stereochemistry , in vitro , medicinal chemistry , organic chemistry , cancer cell , cancer , medicine , biochemistry
The preparation of novel organic disulfides containing the 2‐(substituted phenyl)quinolin‐4(1 H )‐one ring is described. The synthesis starts from thioanthranilic acid esterified with various bromoacetophenones. Cyclization of the resulting phenacyl thioanthranilates in trifluoroacetic acid afforded a mixture of 2‐(substituted phenyl)‐3‐sulfanylquinolin‐4(1 H )‐ones and 3,3′‐disulfanediylbis[2‐(substituted phenyl)quinolin‐4(1 H )‐ones]. Heating of the mixture in o ‐xylene gave 3,3′‐disulfanediylbis[2‐(substituted phenyl)quinolin‐4(1 H )‐ones]of high purity. The disulfides exhibited a significant in vitro cytotoxicity against various cancer cell lines including polyresistant subclones. The data obtained are reported and discussed.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)