Next Article in Journal
Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants
Previous Article in Journal
Antimicrobial and Selected In Vitro Enzyme Inhibitory Effects of Leaf Extracts, Flavonols and Indole Alkaloids Isolated from Croton menyharthii
Article Menu

Export Article

Open AccessArticle
Molecules 2013, 18(10), 12645-12662;

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 / Revised: 25 September 2013 / Accepted: 26 September 2013 / Published: 14 October 2013
(This article belongs to the Section Medicinal Chemistry)
Full-Text   |   PDF [952 KB, uploaded 18 June 2014]   |  


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. View Full-Text
Keywords: imidazole; hydrazones; thiosemicarbazones; antifungal activity imidazole; hydrazones; thiosemicarbazones; antifungal activity

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Supplementary material


Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top