Synthesis, characterization and pharmacological properties of some 4-arylhydrazono-2-pyrazoline-5-one derivatives obtained from heterocyclic amines.
The synthesis of a new series of 4-arylhydrazono-2-pyrazoline-5-ones 7-24 and 22a is described. Structures of the synthesized compounds were confirmed using UV, IR, 1H-NMR, 13C-NMR and EI-mass spectral data. These compounds were tested in vitro against one Gram-positive and two Gram-negative bacterial strains, two mycobacterial strains and a fungus, Candida albicans. Compound 22 was found to be more active against Staphylococcus aureus than the other compounds at a concentration of 15.6 microg/mL. Some related compounds were evaluated for anticonvulsant activity. Compound 11 showed 40% protection against pentylenetetrazole-induced seizures in albino Swiss mice. In vitro antituberculosis activity of 4-arylhydrazono-2-pyrazoline-5-ones 7-12, 14-24, 22a and coupling products 6a-f were tested on Mycobacterium tuberculosis H37Rv. Of these compounds, only 24, which exhibited > 90% inhibition in the primary screen at 12.5 microg/mL against this strain was re-examined for determination of its actual MIC. However, level II assay revealed that the MIC value was not less than 12.5 microg/mL. The same compound was also tested against Mycobacterium avium, which was observed not to be susceptible to 24.
Güniz Küçükgüzel
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Marmara University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Tibbiye cad. No: 81010 Haydarpasa, Istanbul, Turkey.
Rollas
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Erdeniz
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Kiraz
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Cevdet Ekinci
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Vidin
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D000588:Amines / Q000737:chemistry*; D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000927:Anticonvulsants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005260:Female; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011874:Radiometry; D013057:Spectrum Analysis
D000588:Amines; D000890:Anti-Infective Agents; D000927:Anticonvulsants; D006571:Heterocyclic Compounds; D011720:Pyrazoles