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Synthesis and cytotoxic activity of derivatives of 6Z-acetylmethylenepenicillanic acid tert-butyl ester

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Chemistry of Heterocyclic Compounds Aims and scope

The sulfoxide of 6Z-[2-(methoxyimino)propylidene]penicillanic acid tert-butyl ester and the sulfones of 6Z-[2-(hydroxyimino-, methoxyimino-, benzyloxyimino-, 2-bromo- and 4-bromobenzyloxyimino)-propylidene]penicillanic acid in the syn and anti forms have been synthesized by the condensation of the sulfoxide and sulfone of 6Z-acetylmethylenepenicillanic acid tert-butyl ester with hydroxylamine, methoxyamine, benzyloxyamine, 2-bromo- and 4-bromobenzyloxyamines. The syn and anti isomers of 3Z-(2-methoxyiminopropylidene)-4R-(benzothiazolyl-2-dithio)-2-oxoazetidinyl-1R-(2-propenyl)acetic acid tert-butyl ester were obtained by opening of the thiazolidine ring in 6Z-[2-(methoxy-imino)propylidene]-1-oxopenicillanic acid tert-butyl ester with 2-mercaptobenzothiazole. The 3Z-(2-methoxyiminopropylidene)-4R-(methylsulfonyl)-2-oxoazetidinyl-1-(2-propylidene)acetic acid tert-butyl ester was synthesized by the interaction of 1,8-diazobicyclo[5.4.0]undec-7-ene and methyl iodide with 6Z-[2-(methoxyimino)propylidene]-1,1-dioxopenicillanic acid tert-butyl ester. A dependence of the cytotoxic effect in relation to cancer and normal cells in vitro on the structure of the substituent in position 6 and the syn and anti isomerism of the oxyimino group was established for the synthesized compounds.

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Authors and Affiliations

  1. Latvian Institute of Organic Chemistry, Riga, LV-1006, Latvia

    M. Vorona, I. Potorochina, G. Veinberg, S. Belyakov, I. Shestakova, I. Kanepe & E. Lukevics

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  1. M. Vorona
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  2. I. Potorochina
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  3. G. Veinberg
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  4. S. Belyakov
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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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Correspondence to M. Vorona.

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Deceased. (E. Lukevics)

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1897–1905, December, 2009.

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Vorona, M., Potorochina, I., Veinberg, G. et al. Synthesis and cytotoxic activity of derivatives of 6Z-acetylmethylenepenicillanic acid tert-butyl ester. Chem Heterocycl Comp 45, 1532–1538 (2009). https://doi.org/10.1007/s10593-010-0461-x

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  • DOI: https://doi.org/10.1007/s10593-010-0461-x

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