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Synthesis of penicillin derivatives and study of their cytotoxic properties

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

By the interaction of heterocyclic thiols with sulfoxides of 6,6-dihydro- and 6α-chloropenicillanates, derivatives of 4-heteryldithio-2-azetidinones have been synthesized, as well as products of their cyclization to form 2β-heterylthiomethyl-and 2β-halomethyl-substituted penicillanates and an ester of 3-chloro-3-methyl-7α-chlorocepham-4-carboxylic acid. Also, the desulfurization of 6α-chloropenicillanate by Raney nickel has been accomplished. For the substances that have been synthesized, a direct relationship has been established between the intensity of their cytotoxic actionin vitro with respect to tumor cells and the influence of these compounds on the intracellular generation of nitric oxide radicals.

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References

  1. G. Veinberg, I. Shestakova, N. Grigan, D. Musel, I. Kanepe, I. Domrachova, V. Grigoryeva, O. Zharkova, I. Turovskis, I. Kalvinsh, A. Strakovs, and E. Lukevics, Eur. J. Med. Chem. (accepted for publication).

  2. R. G. Micetich, S. N. Maiti, P. Spevak, M. Tanaka, T. Yamazaki, and K. Ogawa, Synthesis, 292 (1986).

  3. Taiho Pharmaceutical Co., Ltd., Jpn. Pat. 58.04788; Chem. Abstr.,98, 197889 (1983).

    Google Scholar 

  4. R. G. Micetich, S. N. Maiti, M. Tanaka, T. Yamazaki, and K. Ogawa, Heterocycles,23, 325 (1985).

    Google Scholar 

  5. K. Prasad, G. Schulz, H. Hamberger, and P. Stutz, Heterocycles,19, 291 (1982).

    Google Scholar 

  6. G. O. Danelon, E. G. Mata, and O. A. Mascaretti, Bioorg. Med. Chem. Lett.,5, 2037 (1995).

    Google Scholar 

  7. C. C. Wei and M. Weigele, Synthesis, 287 (1983).

  8. J. F. Kerwin, Jr., F. R. Lancaster, Jr., and P. L. Feldman, J. Med. Chem.,38, 4343 (1995).

    Google Scholar 

  9. P. J. Freshliey, Culture of Animal Cells (A Manual of Basic Technique), Wiley, New York (1994), p. 296.

    Google Scholar 

  10. D. J. Fast, R. C. Lynch, and R. W. J. El, Leuckocyt. Biol.,52, 255 (1992).

    Google Scholar 

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Authors
  1. G. Veinberg
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  2. R. Bokaldere
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  3. K. Dikovskaya
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  4. M. Vorona
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  5. D. Mucel'
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  6. Kh. Kazhoka
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  7. I. Turovskis
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  8. I. Shestakova
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  9. I. Kanepe
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  10. I. Domracheva
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  11. E. Lukevics
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Additional information

Latvian Institute of Organic Synthesis, Riga LV-1006, Translated from Khimiya Geterosiklicheskikh Soedinenii, No. 11, pp. 1494–1503, November, 1998.

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Veinberg, G., Bokaldere, R., Dikovskaya, K. et al. Synthesis of penicillin derivatives and study of their cytotoxic properties. Chem Heterocycl Compd 34, 1266–1275 (1998). https://doi.org/10.1007/BF02256806

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  • DOI: https://doi.org/10.1007/BF02256806

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