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结构研究及咪唑衍生的硫代缩氨基脲和腙类化合物对作物相关真菌活性的研究。

Structural studies and investigation on the activity of imidazole-derived thiosemicarbazones and hydrazones against crop-related fungi.

机构信息

Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte 31270-901, MG, Brazil.

出版信息

Molecules. 2013 Oct 14;18(10):12645-62. doi: 10.3390/molecules181012645.

DOI:10.3390/molecules181012645
PMID:24129274
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6270485/
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.

摘要

新的咪唑衍生的硫代缩氨基脲和腙是通过 4(5)-咪唑甲醛、4-(1H-咪唑-1-基)苯甲醛和 4-(1H-咪唑-1-基)苯乙酮与硫代缩氨基脲或腙缩合得到的。所有化合物均通过定量元素分析、IR 和 NMR 技术进行了表征。通过单晶 X 射线衍射确定了 8 个结构。评价了化合物的抗真菌活性。这些化合物对黄曲霉和白色念珠菌均没有显著的活性，而 4(5)-咪唑甲醛缩硫代氨基脲（ImT）和 4-(1H-咪唑-1-基)苯甲醛缩硫代氨基脲（4ImBzT）对炭疽状镰孢菌具有高度和选择性的活性。4(5)-咪唑甲醛苯甲酰腙（4(5)ImPh）、4(5)-咪唑甲醛-对氯苯甲酰腙（4(5)ImpClPh）、4(5)-咪唑甲醛-对硝基苯甲酰腙（4(5)ImpNO2Ph）、4-(咪唑-1-基)乙酰苯-对氯苯甲酰腙（4ImAcpClPh）和 4-(咪唑-1-基)乙酰苯-对硝基苯甲酰腙（4ImAcpNO2Ph）对光滑念珠菌具有高度活性。4(5)ImpClPh 和 4(5)ImpNO2Ph 对炭疽状镰孢菌非常有效。在许多情况下，活性优于参考化合物制霉菌素。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb54/6270485/f25f7790364d/molecules-18-12645-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb54/6270485/8468011e73da/molecules-18-12645-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb54/6270485/2c070197b958/molecules-18-12645-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb54/6270485/e52bb04ea4b2/molecules-18-12645-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb54/6270485/f25f7790364d/molecules-18-12645-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb54/6270485/8468011e73da/molecules-18-12645-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb54/6270485/2c070197b958/molecules-18-12645-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb54/6270485/e52bb04ea4b2/molecules-18-12645-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bb54/6270485/f25f7790364d/molecules-18-12645-g004.jpg

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