Synthesis and cytotoxic activity of derivatives of 6<i>Zi>-acetylmethylenepenicillanic acid <i>terti>-butyl ester

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• 作者：M. Vorona ; I. Potorochina ; G. Veinberg ; S. Belyakov ; I. Shestakova ; I. Kanepe and E. Lukevics
• 关键词：tert ; butyl esters of 4R ; (benzothiazolyl ; 2 ; dithio) ; 3Z ; (2 ; methoxyiminopropylidene) ; 2 ; oxo ; azetidinyl ; 1R ; (2 ; propenyl)acetic ; 6Z ; [2 ; (methoxyimino)propylidene] ; 1 ; oxopenicillanic ; 4R ; (methyl ; sulfonyl) ; 3Z ; (2 ; methoxyiminopropylidene) ; 2 ; oxoazetidinyl ; 1 ; (2 ; propyl
• 刊名：Chemistry of Heterocyclic Compounds
• 出版年：2009
• 出版时间：December, 2009
• 年：2009
• 卷：45
• 期：12
• 页码：1532-1538
• 全文大小：563.7 KB

文摘

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.