Design, Synthesis and Evaluate In Vitro Antifungal Activity of Novel Benzamide Derivatives

2019 ◽  
Vol 41 (3) ◽  
pp. 549-549
Author(s):  
Xuesong Wang and Xiaorong Tang Xuesong Wang and Xiaorong Tang
Keyword(s):  
Antifungal Activity ◽  
Pathogenic Fungi ◽  
Gibberella Zeae ◽  
Design Synthesis ◽  
Carboxylic Acid Amides ◽  
Almost All ◽  
Negative Controls ◽  
New Compounds ◽  
Benzamide Derivatives

A series of novel benzamide derivatives according to fluopicolide were designed and synthesized following the rule of combination carboxylic acid amides and amines derivatives together. The antifungal activity of the 15 new compounds were evaluated in vitro against five pathogenic fungi, including Sclerotinia sclerotiorum, Gibberella zeae, Rhizoctonia solani, Helminthosporium maydis and Botrytis cinerea. Almost all the structure have not been reported, except compounds 3, 5 and 6. A surprising finding is that all the five tested fungi breed faster than negative controls when supplementary with compound 715 , respectively.

Activity of Armillarisin B in vitro against Plant Pathogenic Fungi

2009 ◽  
Vol 64 (11-12) ◽  
pp. 790-792 ◽  
Author(s):  
Jin-Wen Shen ◽  
Bing-Ji Ma ◽  
Wen Li ◽  
Hai-You Yu ◽  
Ting-Ting Wu ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Methanolic Extract ◽  
Pathogenic Fungi ◽  
2D Nmr ◽  
Spectroscopic Studies ◽  
Gibberella Zeae ◽  
Plant Pathogenic Fungi ◽  
Fruiting Bodies ◽  
Bioassay Guided Fractionation

The methanolic extract of the fruiting bodies of the mushroom Armillariella tabescens was found to show antifungal activity against Gibberella zeae. The active compound was isolated from the fruiting bodies of A. tabescens by bioassay-guided fractionation of the extract and identifi ed as armillarisin B. Armillarisin B eventually corresponds to 2-hydroxy-2- phenylpropanediamide and its structure was confi rmed on the basis of spectroscopic studies including 2D NMR experiments.

scholarly journals Design, Synthesis and Biological Evaluation of Novel 4-Substituted Coumarin Derivatives as Antitumor Agents

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2281 ◽  
Author(s):  
Ran An ◽  
Zhuang Hou ◽  
Jian-Teng Li ◽  
Hao-Nan Yu ◽  
Yan-Hua Mou ◽  
...  
Keyword(s):  
Antitumor Agents ◽  
Cancer Cell Line ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Hypoxic Conditions ◽  
Ca Ix ◽  
Ic50 Value ◽  
Almost All ◽  
New Compounds

Herein, fifteen new compounds containing coumarin, 1,2,3-triazole and benzoyl- substituted arylamine moieties were designed, synthesized and tested in vitro for their anticancer activity. The results showed that all tested compounds had moderate antiproliferative activity against MDA-MB-231, a human breast cancer cell line, under both normoxic and hypoxic conditions. Furthermore, the 4-substituted coumarin linked with benzoyl 3,4-dimethoxyaniline through 1,2,3-triazole (compound 5e) displayed the most prominent antiproliferative activities with an IC50 value of 0.03 μM, about 5000 times stronger than 4-hydroxycoumarin (IC50 > 100 μM) and 20 times stronger than doxorubicin (IC50 = 0.60 μM). Meanwhile, almost all compounds revealed general enhancement of proliferation-inhibiting activity under hypoxia, contrasted with normoxia. A docking analysis showed that compound 5e had potential to inhibit carbonic anhydrase IX (CA IX).

scholarly journals Synthesis and Bio-Evaluation of Natural Butenolides-Acrylate Conjugates

Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1304 ◽  
Author(s):  
Longzhu Bao ◽  
Shuangshuang Wang ◽  
Di Song ◽  
Jingjing Wang ◽  
Xiufang Cao ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Antifungal Activity ◽  
13C Nmr ◽  
Pathogenic Fungi ◽  
Phytopathogenic Fungi ◽  
Gibberella Zeae ◽  
Ionization Mass ◽  
Activity Screening ◽  
In Vitro Antifungal Activity

A series of novel 3-aryl-4-hydroxy-2(5H) furanone-acrylate hybrids were designed and synthesized based on the natural butenolides and acrylates scaffolds. The structures of the prepared compounds were characterized by 1H-NMR, 13C-NMR and electrospray ionization mass spectrometry (ESI-MS), and the bioactivity of the target compounds against twelve phytopathogenic fungi was investigated. The preliminary in vitro antifungal activity screening showed that most of the target compounds had moderate inhibition on various pathogenic fungi at the concentration of 100 mg·L−1, and presented broad-spectrum antifungal activities. Further studies also indicated that compounds 7e and 7k still showed some inhibitory activity against Pestallozzia theae, Sclerotinia sclerotiorum and Gibberella zeae on rape plants at lower concentrations, which could be optimized as a secondary lead for further research.

scholarly journals Antifungal Activity of Semecarpus anacardium Linn. Oil against Four Phytopathogenic Fungi

2019 ◽  
Vol 2 (3) ◽  
pp. 42-44
Author(s):  
Aarti Patil ◽  
Sadat Quazi
Keyword(s):  
Antifungal Activity ◽  
Fungal Pathogens ◽  
Pathogenic Fungi ◽  
Phytopathogenic Fungi ◽  
Curvularia Lunata ◽  
Semecarpus Anacardium ◽  
Poisoned Food Technique ◽  
Almost All ◽  
In Vitro Antifungal Activity

The present study was undertaken to evaluate in-vitro antifungal activity of Semecarpus anacardium Linn. oil against four fungal pathogens, viz. Curvularia penniseti, Curvularia lunata, Fusarium oxysporum f. sp. ciceris and Helminthosporium maydis using poisoned food technique. The DMSO extract of S.anacardium oil was found to be more or less active against almost all tested pathogenic fungi with a varied spectrum of reduced growth. C.lunata has shown 93.3% inhibition and F.oxysporum and H.maydis have shown 94.4% inhibition and 100% mycelial inhibitions at 15% and 18% concentrations of the extract respectively. Whereas, C.penniseti was found to be quite sensitive that showed 88.9 inhibitions at 10% concentration but it showed 100% inhibition at 18% concentration.  

scholarly journals Novel Fluorinated 7-Hydroxycoumarin Derivatives Containing an Oxime Ether Moiety: Design, Synthesis, Crystal Structure and Biological Evaluation

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 372
Author(s):  
Qing-Qing Wang ◽  
Shu-Guang Zhang ◽  
Jian Jiao ◽  
Peng Dai ◽  
Wei-Hua Zhang
Keyword(s):  
Antifungal Activity ◽  
Positive Control ◽  
Biological Evaluation ◽  
Gibberella Zeae ◽  
X Ray Diffraction ◽  
Oxime Ether ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
Better Than

A series of fluorinated 7-hydroxycoumarin derivatives containing an oxime ether moiety have been designed, synthesized and evaluated for their antifungal activity. All the target compounds were determined by 1H-NMR, 13C-NMR, FTIR and HR-MS spectra. The single-crystal structures of compounds 4e, 4h, 5h and 6c were further confirmed using X-ray diffraction. The antifungal activities against Botrytis cinerea (B. cinerea), Alternariasolani (A. solani), Gibberella zeae (G. zeae), Rhizoctorzia solani (R. solani), Colletotrichum orbiculare (C. orbiculare) and Alternaria alternata (A. alternata) were evaluated in vitro. The preliminary bioassays showed that some of the designed compounds displayed the promising antifungal activities against the above tested fungi. Strikingly, the target compounds 5f and 6h exhibited outstanding antifungal activity against B. cinerea at 100 μg/mL, with the corresponding inhibition rates reached 90.1 and 85.0%, which were better than the positive control Osthole (83.6%) and Azoxystrobin (46.5%). The compound 5f was identified as the promising fungicide candidate against B. cinerea with the EC50 values of 5.75 μg/mL, which was obviously better than Osthole (33.20 μg/mL) and Azoxystrobin (64.95 μg/mL). Meanwhile, the compound 5f showed remarkable antifungal activities against R. solani with the EC50 values of 28.96 μg/mL, which was better than Osthole (67.18 μg/mL) and equivalent to Azoxystrobin (21.34 μg/mL). The results provide a significant foundation for the search of novel fluorinated 7-hydroxycoumarin derivatives with good antifungal activity.

Design, Synthesis, and Antifungal Activity of Alkyl Gallates Against Plant Pathogenic Fungi In Vitro and In Vivo

2021 ◽  
Vol 57 (1) ◽  
pp. 38-43
Author(s):  
Xiao-Long Zhao ◽  
Chun-Qing Li ◽  
Xiao-Mei Song ◽  
Shuang-Mei Yan ◽  
Du-Qiang Luo
Keyword(s):  
Antifungal Activity ◽  
Pathogenic Fungi ◽  
Plant Pathogenic Fungi ◽  
Design Synthesis ◽  
Alkyl Gallates

scholarly journals Antifungal Activity of the Essential Oil of Echinops kebericho Mesfin: An In Vitro Study

2020 ◽  
Vol 2020 ◽  
pp. 1-7
Author(s):  
Tamirat Bekele Beressa ◽  
Serawit Deyno ◽  
Paul E. Alele
Keyword(s):  
Candida Albicans ◽  
Antifungal Activity ◽  
Essential Oil ◽  
Cryptococcus Neoformans ◽  
Antioxidant Properties ◽  
Pathogenic Fungi ◽  
Diffusion Method ◽  
Potential Candidate ◽  
Standard Drug

Background. Echinops kebericho is an endemic medicinal plant in Ethiopia widely used in the treatment of infectious and noninfectious diseases. Essential oils are known for their antibacterial, antifungal, antiviral, insecticidal, and antioxidant properties. This study evaluated the antifungal activity of essential oil from E. kebericho against four common pathogenic fungi and two standard strains. Methods. The essential oil was obtained by hydrodistillation. The antifungal screening was done by agar well diffusion method. Minimal inhibitory concentrations (MICs) were determined by broth microdilution. Minimal fungicidal concentrations (MFCs) were determined by subculturing fungal strains with no visible growth onto a Sabouraud dextrose agar (SDA) plate. Results. Candida albicans and Cryptococcus neoformans were highly sensitive while Aspergillus flavus did not show sensitivity up to 1 mg/ml of essential oil; MICs ranged from 0.083 mg/ml to 0.208 mg/ml. Concentration and fungal species showed significant dose-dependent associations ( p < 0.0001 ) with antifungal activity. The MICs of essential oil were comparable to those of the standard drug (fluconazole) against C. glabrata and C. krusei. The lowest MFC of the essential oil was observed against Candida parapsilosis (0.145 mg/ml) while the highest MFC was against Candida krusei (0.667 mg/ml). Conclusion. Echinops kebericho essential oil showed noteworthy antifungal activity against Cryptococcus neoformans, Candida albicans, and Candida glabrata and could be a potential candidate for further antifungal drug development.

scholarly journals Hevein-Like Antimicrobial Peptides Wamps: Structure–Function Relationship in Antifungal Activity and Sensitization of Plant Pathogenic Fungi to Tebuconazole by WAMP-2-Derived Peptides

2020 ◽  
Vol 21 (21) ◽  
pp. 7912 ◽  
Author(s):  
Tatyana Odintsova ◽  
Larisa Shcherbakova ◽  
Marina Slezina ◽  
Tatyana Pasechnik ◽  
Bakhyt Kartabaeva ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Antimicrobial Peptides ◽  
Structure Function ◽  
Spore Germination ◽  
Pathogenic Fungi ◽  
Plant Pathogenic Fungi ◽  
Fungal Cell ◽  
Structure Function Relationship ◽  
Function Relationship

Hevein-like antimicrobial peptides (AMPs) comprise a family of plant AMPs with antifungal activity, which harbor a chitin-binding site involved in interactions with chitin of fungal cell walls. However, the mode of action of hevein-like AMPs remains poorly understood. This work reports the structure–function relationship in WAMPs—hevein-like AMPs found in wheat (Triticum kiharae Dorof. et Migush.) and later in other Poaceae species. The effect of WAMP homologues differing at position 34 and the antifungal activity of peptide fragments derived from the central, N- and C-terminal regions of one of the WAMPs, namely WAMP-2, on spore germination of different plant pathogenic fungi were studied. Additionally, the ability of WAMP-2-derived peptides to potentiate the fungicidal effect of tebuconazole, one of the triazole fungicides, towards five cereal-damaging fungi was explored in vitro by co-application of WAMP-2 fragments with Folicur® EC 250 (25% tebuconazole). The antifungal activity of WAMP homologues and WAMP-2-derived peptides varied depending on the fungus, suggesting multiple modes of action for WAMPs against diverse pathogens. Folicur® combined with the WAMP-2 fragments inhibited the spore germination at a much greater level than the fungicide alone, and the type of interactions was either synergistic or additive, depending on the target fungus and concentration combinations of the compounds. The combinations, which resulted in synergism and drastically enhanced the sensitivity to tebuconazole, were revealed for all five fungi by a checkerboard assay. The ability to synergistically interact with a fungicide and exacerbate the sensitivity of plant pathogenic fungi to a commercial antifungal agent is a novel and previously uninvestigated property of hevein-like AMPs.

scholarly journals 1346. The Tetrazole VT-1598 Is Efficacious in a Murine Model of Invasive Aspergillosis with a PK/PD Expected of a Mold-Active CYP51 Inhibitor

2018 ◽  
Vol 5 (suppl_1) ◽  
pp. S411-S412
Author(s):  
Edward P Garvey ◽  
Andrew Sharp ◽  
Peter Warn ◽  
Christopher M Yates ◽  
Robert J Schotzinger
Keyword(s):  
Antifungal Activity ◽  
Invasive Aspergillosis ◽  
Murine Model ◽  
Pathogenic Fungi ◽  
Rational Drug Design ◽  
Fungal Burden ◽  
Delayed Treatment ◽  
Rational Drug

Abstract Background VT-1598 is a novel fungal CYP51 inhibitor with potent in vitro activity against yeast, mold, and endemic pathogenic fungi (Wiederhold, JAC, 2017). Its tetrazole-based rational drug design imparts much greater selectivity vs. human CYPs (Yates, BMCL, 2017), which could reduce human CYP-related side effects and DDIs. We report here VT-1598’s in vivo activity in an invasive aspergillosis (IA) model. Methods MIC was determined as outlined in CLSI M38-A2. Plasma PK was measured after 4 days of oral doses in neutropenic ICR mice without fungal inoculation. In vivo antifungal activity was determined in a tail-vein IA model in neutropenic mice inoculated with A. fumigatus (AF) ATCC 204305 (N = 10 per dose). Two separate studies were conducted, with oral VT-1598 treatment starting either 48 hours prior (prophylaxis) or 5 hours postinoculation (delayed), with 4 days of postinoculation dosing, and kidney fungal burden measured 1 day post last dose by both CFU and qPCR. Drug control was 10 mg/kg AmBisome i.v. Results The MIC for VT-1598 against AF 204305 was 0.25 μg/mL. The plasma PK of VT-1598 was linearly proportional between the 5 and 40 mg/kg once-daily doses, with AUCs of 155 and 1,033 μg h/mL for the two doses, respectively. VT-1598 was similarly effective in reducing fungal burden when given in delayed treatment compared with prophylaxis, and both studies demonstrated a full dose–response (i.e., no to full reduction of fungal burden). When comparing fungal burdens of each dose group to the fungal burden at the start of treatment, the dose of VT-1598 to achieve fungal stasis ranged from 20.5 to 25.9 mg/kg and to achieve a 1-log10 fungal kill ranged from 30.9 to 50.5 mg/kg. Using the previously measured mouse plasma binding (&gt;99.9%), the free AUC /MIC values for stasis and 1-log10 kill ranged from 2.1–2.7 and 3.2–5.2, respectively. These values are within the range of 1–11 that have been reported for posaconazole and isavuconazole (Lepak, AAC, 2013). Conclusion VT-1598 had potent antifungal activity in a murine model of IA. The PK/PD relationship was the same as clinically used mold-active CYP51 agents, suggesting that it could have similar clinical efficacy. If correct, the tetrazole-based greater selectivity may significantly differentiate VT-1598 from current IA therapies. Disclosures E. P. Garvey, Viamet Pharmaceuticals, Inc.: Employee, Salary. A. Sharp, Evotec (UK) Ltd.: Employee, Salary. P. Warn, Evotec (UK) Ltd.: Employee, Salary. C. M. Yates, Viamet Pharmaceuticals, Inc.: Employee, Salary. R. J. Schotzinger, Viamet Pharmaceuticals, Inc.: Board Member and Employee, Salary.

scholarly journals Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5852
Author(s):  
Hui Bai ◽  
Xuelian Liu ◽  
Pengfei Chenzhang ◽  
Yumei Xiao ◽  
Bin Fu ◽  
...  
Keyword(s):  
High Resolution Mass Spectrometry ◽  
Binding Modes ◽  
Oxime Ether ◽  
Single Crystal Diffraction ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
Triazole Derivatives ◽  
Pyridine Moiety ◽  
New Compounds

A series of novel 1,2,4-triazole derivatives containing oxime ether and phenoxy pyridine moiety were designed and synthesized. The new compounds were identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS). Compound (Z)-1-(6-(4-nitrophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a18) was further confirmed by X-ray single crystal diffraction. Their antifungal activities were evaluated against eight phytopathogens. The in vitro bioassays indicated that most of the title compounds displayed moderate to high fungicidal activities. Compound (Z)-1-(6-(4-bromo-2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a4) exhibited a broad-spectrum antifungal activities with the EC50 values of 1.59, 0.46, 0.27 and 11.39 mg/L against S. sclerotiorum, P. infestans, R. solani and B. cinerea, respectively. Compound (Z)-1-(6-(2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-benzyl oxime (5b2) provided the lowest EC50 value of 0.12 mg/L against S. sclerotiorum, which were comparable to the commercialized difenoconazole. Moreover, homologous modeling and molecular docking disclosed possible binding modes of compounds 5a4 and 5b2 with CYP51. This work provided useful guidance for the discovery of new 1,2,4-triazole fungicides.

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