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1H NMR analysis revealed the presence of a single signal set due to the quick chemical exchange between the three tautomeric forms.
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1H NMR analysis revealed the presence of a single signal set due to the quick chemical exchange between the three tautomeric forms.
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NOE interactions between benzyl protons and methyl at C3 was revealed, whereas no NOE interactions between benzyl and p-chlorophenyl protons were observed.
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NOE interactions between benzyl protons and methyl at C3 was revealed, whereas no NOE interactions between benzyl and p-chlorophenyl protons were observed.
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The weaker activity of fluoro-derivative 3 seems to be in contrast with pharmacophoric investigations and biological data of the other N1-p-halogen compounds. However, we hypothesised that the electron-withdrawing fluorine atom might have an inductive effect on the pyrazole nucleus and alteration of its electronic nature might resolve into a loss of activity.
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The weaker activity of fluoro-derivative 3 seems to be in contrast with pharmacophoric investigations and biological data of the other N1-p-halogen compounds. However, we hypothesised that the electron-withdrawing fluorine atom might have an inductive effect on the pyrazole nucleus and alteration of its electronic nature might resolve into a loss of activity.
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