Literature DB >> 4043316

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

P J Islip, M V Bogunović-Batchelor.   

Abstract

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 as 1 to the as yet unidentified reduced active but toxic entities formed in vivo from nitroheterocyclics like metronidazole is discussed.

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Year:  1985        PMID: 4043316     DOI: 10.1007/bf01952092

Source DB:  PubMed          Journal:  Experientia        ISSN: 0014-4754


  7 in total

1.  Acetamide--a metabolite of metronidazole formed by the intestinal flora.

Authors:  R L Koch; E J Chrystal; B B Beaulieu; P Goldman
Journal:  Biochem Pharmacol       Date:  1979-12-15       Impact factor: 5.858

2.  Antiparasitic 5-nitrothiazoles and 5-nitro-4-thiazolines. 2.

Authors:  P J Islip; M D Closier; J E Weale
Journal:  J Med Chem       Date:  1973-09       Impact factor: 7.446

3.  Antiparasitic 5-nitrothiazoles and 5-nitro-4-thiazolines. 3.

Authors:  P J Islip; M D Closier; M C Neville
Journal:  J Med Chem       Date:  1973-09       Impact factor: 7.446

4.  The anaerobic metabolism of metronidazole forms N-(2-hydroxyethyl)-oxamic acid.

Authors:  R L Koch; P Goldman
Journal:  J Pharmacol Exp Ther       Date:  1979-03       Impact factor: 4.030

5.  1-Alkyl-3-(3-alkyl-5-nitro-4-thiazolin-2-ylidene)ureas and related compounds as schistosomicides.

Authors:  L M Werbel; M B Degnan; G F Harger; D B Capps
Journal:  J Med Chem       Date:  1972-09       Impact factor: 7.446

6.  Antiparasitic 5-nitrothiazoles and 5-nitro-4-thiazolines. 4.

Authors:  P J Islip; M D Closier; M C Neville
Journal:  J Med Chem       Date:  1974-02       Impact factor: 7.446

7.  Schistosomicidal 5-nitro-4-thiazolines.

Authors:  P J Islip; M D Closier; M C Neville
Journal:  J Med Chem       Date:  1972-09       Impact factor: 7.446

  7 in total

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