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  • Title: Synthesis and in vitro antitumor activity of novel series 2-benzylthio-4-chlorobenzenesulfonamide derivatives.
    Author: Sławiński J, Brzozowski Z.
    Journal: Eur J Med Chem; 2006 Oct; 41(10):1180-9. PubMed ID: 16777268.
    Abstract:
    Three series of novel 2-benzylthio-4-chloro-5-R1-benzenesulfonamides bearing the N-(benzoxazol-2-yl) (10-19), N-(benzothiazol-2-yl) (20-21) or N-(1,3-dihydro-2H-benzimidazol-2-ylidene) (22-25) moiety were synthesized by reacting N-(2-benzylthio-4-chloro-5-R1-benzenesulfonyl)cyanamide potassium salts (5-9) with 2-aminophenols, 2-aminothiophenol and o-phenylenediamines, respectively. Compounds with carbamoyl substituent at position 5 (14-16, 21 and 25, R1=CONH2) were further dehydrated to the corresponding nitriles (26-30, R1=CN). The in vitro antitumor activity of the compounds obtained was determined at the National Cancer Institute (NCI), and the structure-activity relationships were discussed. N-(2-benzoxazolyl)-2-benzylthio-4-chloro-5-(4-fluorophenylcarbamoyl)benzenesulfonamide (18) is the prominent of the compounds due to its remarkable activity and selectivity toward non-small cell lung cancer (NCI-H522) and melanoma (SK-MEL-2) cell lines (GI50=0.1 microM, TGI=0.5-0.6 microM).
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