SYNTHESIS OF CYTOTOXIC 4-SULFONYL-, 4-SULFONYLTHIO- AND 4-SULFOTHIOAZETIDINONES-2

Authors

  • G. Veinberg Latvian Institute of Organic Synthesis, Riga LV 1006
  • M. Vorona Latvian Institute of Organic Synthesis, Riga LV 1006
  • D. Musel Latvian Institute of Organic Synthesis, Riga LV 1006
  • R. Bokaldere Latvian Institute of Organic Synthesis, Riga LV 1006
  • I. Shestakova Latvian Institute of Organic Synthesis, Riga LV 1006
  • I. Kanepe Latvian Institute of Organic Synthesis, Riga LV 1006
  • E. Lukevics Latvian Institute of Organic Synthesis, Riga LV 1006

Keywords:

2-[4-sulfonyl-2-oxoazetidinyl-1]-2-(isopropyliden)acetic acid esters, 2-[4-sulfonylthio-2-oxoazetidinyl-1]-, and 2-[4-sulfothio-2-oxoazetidinyl-1]-2-(isopropenyl)acetic acid esters, cytotoxic activity

Abstract

4-Sulfonylazetidinones-2 were synthesized by the reaction of DBU and organic halides with the esters of penicillin sulfones. 4-Sulfonylthio- and 4-sulfothioazetidinones-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.

How to Cite
Veinberg, G.; Vorona, M.; Musel, D.; Bokaldere, R.; Shestakova, I.; Kanepe, I.; Lukevics, E. Chem. Heterocycl. Compd. 2004, 40, 816. [Khim. Geterotsikl. Soedin. 2004, 949.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000040782.42204.4f

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Published

2004-06-25

Issue

No. 6 (2004)

Section

Original Papers