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Synthesis of Cytotoxic 4-Sulfonyl-, 4-Sulfonylthio-and 4-Sulfothioazetidinones-2

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

4-Sulfonylazetidinones-2 were synthesized by the reaction of DBU and organic halides on the esters of penicillin sulfones. 4-Sulfonylthio- and 4-sulfothioazetindinones-2 were synthesized by nucleophilic substitution of the 2-benzothiazolylthio groups in 4-(benzothiazolylthio)azetidinones-2 using sodium sulfinates or sodium hydrogen sulfite. A study of their cytotoxic activities revealed the anticancer effect of compounds containing methylsulfonylthio-, 4-tolylsulfonylthio-, and 4-methoxycarbonylamino-phenylsulfonylthio-substituents at position 4 of the β-lactam ring relative to a wide range of monolayer cultures of cancer cells in vitro.

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  1. Latvian Institute of Organic Synthesis, Riga, LV-1006

    G. Veinberg, M. Vorona, D. Musel, R. Bokaldere, I. Shestakova, I. Kanepe & E. Lukevics

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  1. G. Veinberg
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  2. M. Vorona
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  3. D. Musel
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  4. R. Bokaldere
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  5. I. Shestakova
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  6. I. Kanepe
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  7. E. Lukevics
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Veinberg, G., Vorona, M., Musel, D. et al. Synthesis of Cytotoxic 4-Sulfonyl-, 4-Sulfonylthio-and 4-Sulfothioazetidinones-2. Chemistry of Heterocyclic Compounds 40, 816–822 (2004). https://doi.org/10.1023/B:COHC.0000040782.42204.4f

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  • DOI: https://doi.org/10.1023/B:COHC.0000040782.42204.4f

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