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5-(Hydroxyimino)-4-methoxy-2-(pivaloylimino)thiazolidine-3-acetamide, a reduced nitroheterocyclic derivative with potent schistosomicidal properties

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Summary

The synthesis and antischistosome properties of 5-(hydroxyimino)-4-methoxy-2-(pivaloylimino)thiazolidine-3-acetamide (1) are described. The compound was prepared by reduction of the nitrothiazoline (2) with stannous chloride in methanol, and represents the first example of a reduced nitroheterocyclic compound showing potent schistosomicidal properties. The possible relationship of compounds such as1 to the as yet unidentified reduced active but toxic entities formed in vivo from nitroheterocyclics like metronidazole is discussed.

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References

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Authors and Affiliations

  1. Medicinal Chemistry Laboratories, Wellcome Research Laboratories, Langley Court, BR3 3BS, Beckenham, Kent, (England)

    P. J. Islip & M. V. Bogunović-Batchelor

Authors
  1. P. J. Islip
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  2. M. V. Bogunović-Batchelor
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Additional information

Acknowledgments. The authors are grateful to Dr A. J. Everett and his staff for the physical chemistry measurements, and to Mr G. Dickerson for the antischistosome testing.

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Islip, P.J., Bogunović-Batchelor, M.V. 5-(Hydroxyimino)-4-methoxy-2-(pivaloylimino)thiazolidine-3-acetamide, a reduced nitroheterocyclic derivative with potent schistosomicidal properties. Experientia 41, 1353–1354 (1985). https://doi.org/10.1007/BF01952092

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  • DOI: https://doi.org/10.1007/BF01952092

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