Structural Studies and Investigation on the Activity of Imidazole-Derived Thiosemicarbazones and Hydrazones against Crop-Related Fungi

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)-imidazolecarboxaldehydepara-chlorobenzoyl hydrazone (4(5)ImpClPh), 4(5)-imidazolecarboxaldehyde-paranitrobenzoyl hydrazone (4(5)ImpNO 2 Ph), 4-(imidazole-1-yl)acetophenone-para-chlorobenzoyl hydrazone (4ImAcpClPh) and 4-(imidazole-1-yl)acetophenone-para-nitrobenzoylhydrazone (4ImAcpNO 2 Ph) were highly active against Candida glabrata. 4(5)ImpClPh and 4(5)ImpNO 2 Ph were very effective against C. cladosporioides. In many cases, activity was superior to that of the reference compound nystatin.

Synthesis and in vitro antifungal activity of isoniazid-derived hydrazones against Coccidioides posadasii

“…Among such compounds, [10] and Cladosporium cladosporioides [31]. In addition, hydrazones also display many pharmacological properties such as antiinflammatory, analgesic, anticancer, antiplatelet and anticonvulsant, besides broad antimicrobial activity [25].…”

A Decade of Development of Ethylidenethiosemicarbazides as Building Blocks for Synthesis of Azoles and Azines (A Review)

“…Recently, ethylidenethiosemicarbazides have been used as effective pharmacophoric agents in medicinal chemistry such as; antitumor 1 , anti-tubercular 2 , anti-amoebic 3 , anti-fungal 4 , antiviral 5 , antimicrobial 6 , antioxidant 7 , anticonvulsant 8 , and anti-trypanosomal 9,10 . Also, these compounds were prescribed for treatment of hypertension as calcium channel blockers 11 .…”

“…The biological activity of ethylidenethiosemicarbazides is related to their chelating ability with metal ion through either thione or thiolate sulfur and one of the hydrazone-nitrogen atoms 12 . Furthermore, ethylidenethiosemicarbazides have been used as a reactive building blocks for synthesis of different azoles such as, bis-thiazoles 13 , [1,3,4]thiadiazoles 14 , [1,3,4]oxadiazoles 15 , thiazolidin-4-ones 16 , imidazolinones 17 , and thiazoles 18,19 . In this survey, we represent three approaches about ethylidenethiosemicarbazides, with different aryl or heterocyclic moieties, including synthesis, reactivity, and their biological activities.…”

“…[4] 3,4-F 2 C 6 H 3 [25] [6] 4-BrC 6 H 4 [26] 3,4-Cl 2 C 6 H 3 [9] 4-CH 3 [ The reactivity of thiosemicarbazones 3 or 5 towards N-aryl carbohydrazonoyl chlorides 10, without keto group, has been reported 18,19,84 under thermal 19,84 or microwave irradiation and using grafted chitosan 18 or triethylamine 19,84 as basic catalyst. These reactions have been established to give [1,3,4]thiadiazoles11 (Scheme 4). Reaction with chloroethanoic acidor ethyl α α α α α-haloalkanoate Cyclocondensation of ethylidenehydrazine-1-carbothiamides3 or 5 with chloroethanoic acid (28) in ethanolic solution, containing anhydrous sodium acetate afforded thiazole-4(5H)-one derivatives 7,8,26,45,57,60 29 (Scheme 13).…”

Nickel Complexes Bearing SNN and SS Donor Atom Ligands: Synthesis, Structural Characterization and Biological activity

“…Thiosemicarbazones (TSCs) are a class of SN donor atom ligands displaying a wide spectrum of biological activities; since they were introduced, they have gained great interest to medicinal chemists . Of those medicinally important TSCs, the tridentate SNN Schiff base ligand pyridine‐2‐carboxaldehyde thiosemicarbazone proved to possess potent anticancer activity .…”