Abstract
For probing the importance of planarity of imidazolidinone motif of 4-phenyl-1-(benzenesulfonyl)imidazolidinones1 for their cytotoxicity, 4-phenyl-2-(benzoyl)[1,2,5]thiadiazolidine-1,1-dioxide (2a), 4-phenyl-2-(p-toluoyl)[1,2,5]thiadiazolidine-1,1-dioxide (2b), 4-phenyl-2-(phenylcarbamoyl) [1,2,5]thiadiazolidine-1,1-dioxide (3a), and 4-phenyl-2-(p-tolylcarbamoyl)[1,2,5]thiadiazolidine-1,1-dioxide (3b) were prepared along with their regioisomers (5a, 5b, 9a, 9b) and their cytotoxicity were measured against human lung carcinoma (A549), human colon carcinoma (COLO205), human ovarian cancer (SK-OV-3), human leukemic cancer (K562), and murine colon adenocarcinoma (Colon26) cell linesin vitro. All compounds prepared do not show any activity against all five cancer cell lines unlike1. Compounds1 possess planarity of imidazolidinone, especially in sulfonylurea moiety (-SO2NHCONH-). However compounds2 and3 have nonplanar 5-membered ring, [1,2,5]thiadiazolidine-1,1-dioxides. Such structural differentiation might result in the loss of activity. Therefore the inactivity of2 and3 could also be an indication for the necessity of planarity of imidazolidinone ring of1 for their cytotoxic activity.
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Kim, IW., Lee, CK., Kim, H.S. et al. Importance of sulfonylimidazolidinone motif of 4-phenyl-1-arylsulfonylimidazolidinones for their cytotoxicity: Synthesis of 2-benzoyl-4-phenyl[1,2,5]thiazolidine-1,1-dioxides and their cytotoxcity. Arch Pharm Res 26, 9–14 (2003). https://doi.org/10.1007/BF03179923
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DOI: https://doi.org/10.1007/BF03179923