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  • Title: Synthesis, immunological activity and computational study of 5-amino-3-methyl-4-isoxazolecarboxylic acid semicarbazides and thiosemicarbazides.
    Author: Maczyński M, Zimecki M, Taraszkiewicz M, Ryng S.
    Journal: Acta Pol Pharm; 2008; 65(5):543-9. PubMed ID: 19051600.
    Abstract:
    A series of 5-amino-3-methyl-4-isoxazolecarboxylic acid semicarbazides and thiosemicarbazides (M1-M9) were obtained by reacting 5-amino-3-methyl-4-isoxazolecarboxylic acid hydrazide with isocyanate and isothiocyanate. In order to determine structure-activity relationships for the series of nine compounds (M1-M9) geometry optimization was carried out using quantum-chemical DFT calculations at B3LYP/6-31g* level. The compounds, administered to mice at 1 microg or 10 microg doses, four hours prior to immunization with sheep erythrocytes (SRBC), significantly suppressed the primary, humoral immune response in mice as measured by the number of antibody-forming cells (AFC) in the spleens. Structure/activity relationships, regarding the studied compounds, were discussed.
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