101092-40-4Relevant academic research and scientific papers
Design, synthesis, biological evaluation, molecular docking, DFT calculations and in silico ADME analysis of (benz)imidazole-hydrazone derivatives as promising antioxidant, antifungal, and anti-acetylcholinesterase agents
Amine Khodja, Imene,Belfaitah, Ali,Bensouici, Chawki,Boulebd, Houssem
, (2020)
Ten hydrazone derivatives bearing a (benz)imidazole nucleus were designed, synthesized and evaluated for their antioxidant, antifungal, and anti-acetylcholinesterase activities. All the synthesized compounds (1-10) showed good to excellent antioxidant activity. Among them, compound 10 was found to be the best acetylcholinesterase inhibitor with an IC50 value comparable to that of the galantamine. Compound 5 was found to be the best antifungal agent against Fusarium oxysporum fungal strain when compared to the commercial fungicide carbendazim. DFT calculations, for representative molecules 1 and 6, were also performed to investigate the antioxidant mechanisms, and it was found that SETPT (sequential electron transfer-proton transfer) is the most favorable mechanism in ethanol. Molecular docking studies of the most active compounds were carried out, and results showed reasonable binding modes in the active site of Fusarium oxysporum FGB1 enzyme and acetylcholinesterase. Finally, in silico predictions of ADME and pharmacokinetic parameters indicated that these compounds should have good oral bioavailability.
Synthesis and biological evaluation of benzimidazole phenylhydrazone derivatives as antifungal agents against phytopathogenic fungi
Wang, Xing,Chen, Yong-Fei,Yan, Wei,Cao, Ling-Ling,Ye, Yong-Hao
, (2016/12/03)
A series of benzimidazole phenylhydrazone derivatives (6a-6ai) were synthesized and characterized by 1H-NMR, ESI-MS, and elemental analysis. The structure of 6b was further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity against Rhizoctonia solani and Magnaporthe oryzae employing a mycelium growth rate method. Compound 6f exhibited significant inhibitory activity against R. solani and M. oryzae with the EC50 values of 1.20 and 1.85 μg/mL, respectively. In vivo testing demonstrated that 6f could effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound 6f with a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides.
