Design and synthesis of antifungal benzoheterocyclic derivatives by scaffold hopping

Sheng, Chunquan; Che, Xiaoying; Wang, Wenya; Wang, Shengzheng; Cao, Yongbing; Yao, Jing; Miao, Zhenyuan; Zhang, Wannian

doi:10.1016/j.ejmech.2011.01.075

Cited by 56 publications

(24 citation statements)

References 16 publications

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“…In addition, benzoxazole derivatives possess a variety of biological activities such as antitumor [ 112 , 113 , 114 , 115 ], antituberculosis [ 116 ], antifungal [ 117 ], antimicrobial [ 118 , 119 , 120 , 121 , 122 , 123 ], antihypertension [ 124 ], antiviral [ 97 , 125 ], antihormonal [ 126 ], and radioligand agents [ 127 , 128 , 129 ]. Because of the aforementioned properties of both fluorine and benzazoles, efforts have been done by Nosova et al to summarize several methods of synthesizing fluorinated benzazoles [ 130 ].…”

Section: Benzazolesmentioning

confidence: 99%

Importance of Fluorine in Benzazole Compounds

2020

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Fluorine-containing heterocycles continue to receive considerable attention due to their unique properties. In medicinal chemistry, the incorporation of fluorine in small molecules imparts a significant enhancement their biological activities compared to non-fluorinated molecules. In this short review, we will highlight the importance of incorporating fluorine as a basic appendage in benzothiazole and benzimidazole skeletons. The chemistry and pharmacological activities of heterocycles containing fluorine during the past years are compiled and discussed.

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Section: Benzazolesmentioning

confidence: 99%

Importance of Fluorine in Benzazole Compounds

2020

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“…In addition, both methods used polyphosphoric acid (PPA) as a reactant, which not only caused difficulty in aftertreatment but was also unfriendly to the environment [ 18 , 19 ]. In order to overcome these disadvantages, we reacted 2-aminophenol with ethyl chloroacetimidate hydrochloride in methylene chloride at 0 °C to provide the compound 3 with 86.5% yield according to the method described by Sheng [ 20 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Antifungal Activities and Molecular Docking Studies of Benzoxazole and Benzothiazole Derivatives

Luo

Zhang

et al. 2018

Molecules

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Based on benzoxazole and benzothiazole scaffold as an important pharmacophore, two series of 2-(aryloxymethyl) benzoxazole and benzothiazole derivatives were synthesized and their antifungal effects against eight phytopathogenic fungi were evaluated. Compounds 5a, 5b, 5h, and 5i exhibited significant antifungal activities against most of the pathogens tested. Especially 5a, 5b, 5h, 5i, 5j, and 6h inhibited the growth of F. solani with IC50 of 4.34–17.61 μg/mL, which were stronger than that of the positive control, hymexazol (IC50 of 38.92 μg/mL). 5h was the most potent inhibitor (IC50 of 4.34 μg/mL) against F. Solani, which was about nine times more potent than hymexazol. Most of the test compounds displayed significant antifungal effects against B. cinerea (IC50 of 19.92–77.41 μg/mL), among them, 5a was the best one (IC50 of 19.92 μg/mL). The structure-activity relationships (SARs) were compared and analyzed. The result indicates that the electron-drawing ability and position of the substituents have a significant impact on biological activities. Furthermore, docking studies were carried out on the lipid transfer protein sec14p from S. cerevisiae, and preliminarily verified the antifungal activities. Taken together, these results provide 2-(phenoxymethyl)benzo[d]oxazole as an encouraging framework that could lead to the development of potent novel antifungal agents.

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“…Extensive scaffold hopping studies have been performed to find a better core fragment (Fig. B) . The aminotetralin scaffold and benzoimidazole scaffold were also found to be favorable for the antifungal activity .…”

Section: From Fragments To Leads: De Novo Drug Designmentioning

confidence: 99%

“…B) . The aminotetralin scaffold and benzoimidazole scaffold were also found to be favorable for the antifungal activity . Because these novel inhibitors do not coordinate with the heme and interact with CYP51 mainly through nonbonding interactions, they are promising leads for the development of selective antifungal agents with better safety profiles.…”

Section: From Fragments To Leads: De Novo Drug Designmentioning

confidence: 99%

Fragment Informatics and Computational Fragment‐Based Drug Design: An Overview and Update

Sheng

Zhang

2012

Medicinal Research Reviews

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Fragment-based drug design (FBDD) is a promising approach for the discovery and optimization of lead compounds. Despite its successes, FBDD also faces some internal limitations and challenges. FBDD requires a high quality of target protein and good solubility of fragments. Biophysical techniques for fragment screening necessitate expensive detection equipment and the strategies for evolving fragment hits to leads remain to be improved. Regardless, FBDD is necessary for investigating larger chemical space and can be applied to challenging biological targets. In this scenario, cheminformatics and computational chemistry can be used as alternative approaches that can significantly improve the efficiency and success rate of lead discovery and optimization. Cheminformatics and computational tools assist FBDD in a very flexible manner. Computational FBDD can be used independently or in parallel with experimental FBDD for efficiently generating and optimizing leads. Computational FBDD can also be integrated into each step of experimental FBDD and help to play a synergistic role by maximizing its performance. This review will provide critical analysis of the complementarity between computational and experimental FBDD and highlight recent advances in new algorithms and successful examples of their applications. In particular, fragment-based cheminformatics tools, high-throughput fragment docking, and fragment-based de novo drug design will provide the focus of this review. We will also discuss the advantages and limitations of different methods and the trends in new developments that should inspire future research.

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Design and synthesis of antifungal benzoheterocyclic derivatives by scaffold hopping

Cited by 56 publications

References 16 publications

Importance of Fluorine in Benzazole Compounds

Importance of Fluorine in Benzazole Compounds

Synthesis, Antifungal Activities and Molecular Docking Studies of Benzoxazole and Benzothiazole Derivatives

Fragment Informatics and Computational Fragment‐Based Drug Design: An Overview and Update

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