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Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi
Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte 31270-901, MG, Brazil
* Author to whom correspondence should be addressed.
Received: 14 August 2013; in revised form: 25 September 2013 / Accepted: 26 September 2013 / Published: 14 October 2013
Abstract: New imidazole derived thiosemicarbazones and hydrazones were prepared by condensation of 4(5)-imidazole carboxaldehyde, 4-(1H-imidazole-1-yl)benzaldehyde and 4-(1H-imidazole-1-yl)acetophenone with a thiosemicarbazide or hydrazide. All compounds were characterized by quantitative elemental analysis, IR and NMR techniques. Eight structures were determined by single crystal X-ray diffraction. The antifungal activities of the compounds were evaluated. None of the compounds exhibited significant activity against Aspergillus flavus and Candida albicans, while 4(5)-imidazolecarboxaldehyde thiosemicarbazone (ImT) and 4-(1H-imidazole-1-yl)benzaldehyde thiosemicabazone (4ImBzT) were highly and selectively active against Cladosporium cladosporioides. 4(5)-Imidazolecarboxaldehyde benzoyl hydrazone (4(5)ImPh), 4(5)-imidazolecarboxaldehyde-para-chlorobenzoyl hydrazone (4(5)ImpClPh), 4(5)-imidazolecarboxaldehyde-para-nitrobenzoyl hydrazone (4(5)ImpNO2Ph), 4-(imidazole-1-yl)acetophenone-para-chloro-benzoyl hydrazone (4ImAcpClPh) and 4-(imidazole-1-yl)acetophenone-para-nitro-benzoylhydrazone (4ImAcpNO2Ph) were highly active against Candida glabrata. 4(5)ImpClPh and 4(5)ImpNO2Ph were very effective against C. cladosporioides. In many cases, activity was superior to that of the reference compound nystatin.
Keywords: imidazole; hydrazones; thiosemicarbazones; antifungal activity
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Reis, D.C.; Despaigne, A.A.R.; Silva, J.G.D.; Silva, N.F.; Vilela, C.F.; Mendes, I.C.; Takahashi, J.A.; Beraldo, H. Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi. Molecules 2013, 18, 12645-12662.
Reis DC, Despaigne AAR, Silva JGD, Silva NF, Vilela CF, Mendes IC, Takahashi JA, Beraldo H. Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi. Molecules. 2013; 18(10):12645-12662.
Reis, Débora C.; Despaigne, Angel A.R.; Silva, Jeferson G.D.; Silva, Nayane F.; Vilela, Camila F.; Mendes, Isolda C.; Takahashi, Jacqueline A.; Beraldo, Heloisa. 2013. "Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi." Molecules 18, no. 10: 12645-12662.