Design, synthesis, and structure–activity relationship studies of novel thienopyrrolidone derivatives with strong antifungal activity against Aspergillus fumigates

Cao, Xufeng; Xu, Yuanyuan; Cao, Yongbing; Wang, Ruilian; Zhou, Ran; Chu, Wen‐Jing; Yang, Yushe

doi:10.1016/j.ejmech.2015.08.023

Cited by 32 publications

(10 citation statements)

References 25 publications

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“…At first, 1,3-dichlorobenzene (1.0 equiv), chloroacetyl chloride (ClCH 2 COCl) (1.2 equiv) and anhydrous aluminum chloride (AlCl 3 ) (1.0 equiv) in an anhydrous dichloromethane (DCM) solution were heated at reflux for 4 h to obtain compound 2 in 80% yield. 19) Secondly, intermediate 3 was prepared by condensation of compound 2 (1.0 equiv) with triazole (1.5 equiv) in the presence of potassium carbonate (K 2 CO 3 ) (1.0 equiv) and acetonitrile (CH 3 CN) for 8 h at reflux. Intermediates 3 was obtained in the yield of 39%.…”

Section: Resultsmentioning

confidence: 99%

Novel Triazole Derivatives Containing Different Ester Skeleton: Design, Synthesis, Biological Evaluation and Molecular Docking

et al. 2020

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Invasive fungal disease constitutes a growing health problem and development of novel antifungal drugs with high potency and selectivity are in an urgent need. In this study, a novel series of triazole derivatives containing different ester skeleton were designed and synthesized. Microdilution broth method was used to investigate antifungal activity. Significant inhibitory activity of compounds 5c, 5d, 5e, 5f, 5m and 5n was evaluated against the Candida albicans (I), Candida albicans clinical isolate (II), Candida glabrata clinical isolate (I), and Candida glabrata (II) with minimum inhibitory concentrations (MIC 80 ) values ranging from 2 to 16 µg/mL. Notably, compounds 5e and 5n showed the best inhibition against Candida albicans (II), Candida glabrata (I), and Candida glabrata (II) at the concentrations of 2 and 8 µg/mL, respectively. Molecular docking study revealed that the target compounds interacted with CYP51 mainly through hydrophobic and van der Waals interactions. The results indicated that these novel triazole derivatives could serve as promising leads for development of antifungal agents.

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Section: Resultsmentioning

confidence: 99%

Novel Triazole Derivatives Containing Different Ester Skeleton: Design, Synthesis, Biological Evaluation and Molecular Docking

et al. 2020

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“…154-155 °C (lit. 14 146-148 °C); yield 8.5 g (80% for two steps); 1 H NMR (400 MHz, CDCl 3 ): δ 8.00 (s, 1H), 7.81 (s, 1H), 7.57-7.44 (m, 1H), 6.88-6.72 (m, 2H), 4.78-4.62 (m, 2H), 3.64 (qd, J = 6.5, 2.8 Hz, 1H), 1.30 (br, 2H), 0.87 (d, J = 6.5 Hz, 3H); 13…”

Section: Methodsmentioning

confidence: 99%

Improved Laboratory Synthesis of YC-071, a Potent Azole Antifungal Agent

Zheng

Qian

Ling

et al. 2017

Journal of Chemical Research

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“…One of the most employed methods for the development of new therapeuticals involves identifying bioactive compounds present in plants, animals, and microorganisms [99, 102–106]. In addition, a recent approach applies bioinformatics analysis to search in genomic databases for peptide sequences that have the physical-chemical characteristics of the antifungal drugs [107–109]. This may employ the use of several methodologies, including global approaches such as transcriptomic and proteomic methods that may contribute to the understanding of the mechanism of action of these new drugs [110, 111].…”

Section: Strategies To Develop New Antifungal Agentsmentioning

confidence: 99%

Antifungal Resistance, Metabolic Routes as Drug Targets, and New Antifungal Agents: An Overview about Endemic Dimorphic Fungi

Parente-Rocha

Bailão

Amaral

et al. 2017

Mediators of Inflammation

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Diseases caused by fungi can occur in healthy people, but immunocompromised patients are the major risk group for invasive fungal infections. Cases of fungal resistance and the difficulty of treatment make fungal infections a public health problem. This review explores mechanisms used by fungi to promote fungal resistance, such as the mutation or overexpression of drug targets, efflux and degradation systems, and pleiotropic drug responses. Alternative novel drug targets have been investigated; these include metabolic routes used by fungi during infection, such as trehalose and amino acid metabolism and mitochondrial proteins. An overview of new antifungal agents, including nanostructured antifungals, as well as of repositioning approaches is discussed. Studies focusing on the development of vaccines against antifungal diseases have increased in recent years, as these strategies can be applied in combination with antifungal therapy to prevent posttreatment sequelae. Studies focused on the development of a pan-fungal vaccine and antifungal drugs can improve the treatment of immunocompromised patients and reduce treatment costs.

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Design, synthesis, and structure–activity relationship studies of novel thienopyrrolidone derivatives with strong antifungal activity against Aspergillus fumigates

Cited by 32 publications

References 25 publications

Novel Triazole Derivatives Containing Different Ester Skeleton: Design, Synthesis, Biological Evaluation and Molecular Docking

Novel Triazole Derivatives Containing Different Ester Skeleton: Design, Synthesis, Biological Evaluation and Molecular Docking

Improved Laboratory Synthesis of YC-071, a Potent Azole Antifungal Agent

Antifungal Resistance, Metabolic Routes as Drug Targets, and New Antifungal Agents: An Overview about Endemic Dimorphic Fungi

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