scholarly journals (R)-2-Phenyl-4,5-Dihydrothiazole-4-Carboxamide Derivatives Containing a Diacylhydrazine Group: Synthesis, Biological Evaluation, and SARs

Molecules ◽  
2019 ◽  
Vol 24 (24) ◽  
pp. 4440
Author(s):  
Feng-Yun Li ◽  
Jing-Bo Liu ◽  
Jia-Ning Gong ◽  
Gen Li
Keyword(s):  
Antifungal Activity ◽  
Phytophthora Capsici ◽  
Alternaria Solani ◽  
Biological Evaluation ◽  
Phytopathogenic Fungi ◽  
Cercospora Arachidicola ◽  
Mythimna Separata ◽  
Hydrophilic Group ◽  
Better Than ◽  
Insecticidal Activities

A series of (R)-2-phenyl-4,5-dihydrothiazole-4-carboxamide derivatives containing a diacylhydrazine moiety were designed and synthesized. Their structures were confirmed by melting points, 1H NMR, 13C NMR, and elemental analysis (EA). Their antifungal and insecticidal activities were evaluated. The antifungal activity result indicated that most title compounds against Cercospora arachidicola, Alternaria solani, Phytophthora capsici, and Physalospora piricola exhibited apparent antifungal activities at 50 mg/L, and better than chlorothalonil or carbendazim. The EC50 values of (R)-N’-benzoyl-2-(4-chlorophenyl)-4,5-dihydrothiazole-4-carbohydrazide (I-5) against six tested phytopathogenic fungi were comparable to those of chlorothalonil. The CoMSIA model showed that a proper hydrophilic group in the R1 position, as well as a proper hydrophilic and electron-donating group in the R2 position, could improve the antifungal activity against Physalospora piricola, which contributed to the further optimization of the structures. Meanwhile, most title compounds displayed good insecticidal activities, especially compound (R)-N’-(4-nitrobenzoyl)-2-(4-nitrophenyl)-4,5-dihydrothiazole-4-carbohydrazide (III-3). The insecticidal mechanism results indicated that compound III-3 can serve as effective insect Ca2+ level modulators by disrupting the cellular calcium homeostasis in Mythimna separata.

scholarly journals Synthesis, Antifungal Activity, and 3D-QSAR Study of Novel Nopol-Derived 1,3,4-Thiadiazole-Thiourea Compounds

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1708
Author(s):  
Ming Chen ◽  
Wen-Gui Duan ◽  
Gui-Shan Lin ◽  
Zhong-Tian Fan ◽  
Xiu Wang
Keyword(s):  
Antifungal Activity ◽  
Alternaria Solani ◽  
3D Qsar ◽  
Qsar Model ◽  
Gibberella Zeae ◽  
Cercospora Arachidicola ◽  
Qsar Study ◽  
Structure Activity ◽  
Better Than

A series of novel nopol derivatives bearing the 1,3,4-thiadiazole-thiourea moiety were designed and synthesized by multi-step reactions in search of potent natural product-based antifungal agents. Their structures were confirmed by FT-IR, NMR, ESI-MS, and elemental analysis. Antifungal activity of the target compounds was preliminarily evaluated by in vitro methods against Fusarium oxysporum f. sp. cucumerinum, Cercospora arachidicola, Physalospora piricola, Alternaria solani, Gibberella zeae, Rhizoeotnia solani, Bipolaris maydis, and Colleterichum orbicalare at 50 µg/mL. All the target compounds exhibited better antifungal activity against P. piricola, C. arachidicola, and A. solani. Compound 6j (R = m, p-Cl Ph) showed the best broad-spectrum antifungal activity against all the tested fungi. Compounds 6c (R = m-Me Ph), 6q (R = i-Pr), and 6i (R = p-Cl Ph) had inhibition rates of 86.1%, 86.1%, and 80.2%, respectively, against P. piricola, much better than that of the positive control chlorothalonil. Moreover, compounds 6h (R = m-Cl Ph) and 6n (R = o-CF3 Ph) held inhibition rates of 80.6% and 79.0% against C. arachidicola and G. zeae, respectively, much better than that of the commercial fungicide chlorothalonil. In order to design more effective antifungal compounds against A. solani, analysis of the three-dimensional quantitative structure–activity relationship (3D-QSAR) was carried out using the CoMFA method, and a reasonable and effective 3D-QSAR model (r2 = 0.992, q2 = 0.753) has been established. Furthermore, some intriguing structure–activity relationships were found and are discussed by theoretical calculation.

scholarly journals Facile synthesis and antifungal activity of dithiocarbamate derivatives bearing an amide moiety

2015 ◽  
Vol 80 (11) ◽  
pp. 1367-1374 ◽  
Author(s):  
Yu-Wen Li ◽  
Shu-Tao Li
Keyword(s):  
Antifungal Activity ◽  
Fusarium Solani ◽  
High Resolution Mass Spectrometry ◽  
Alternaria Solani ◽  
Phytopathogenic Fungi ◽  
Gibberella Zeae ◽  
Significant Activity ◽  
Facile Synthesis ◽  
Dithiocarbamate Derivatives

A series of novel dithiocarbamate derivatives bearing amide moiety 3a-3i and 4a-4i were synthesized by a facile method, and the structures of these derivatives were confirmed by 1H NMR, 13C NMR, elemental analysis and high-resolution mass spectrometry (HRMS). Their antifungal activity against five phytopathogenic fungi were evaluated, and the results showed that most of the target compounds displayed low antifungal activity in vitro against Gibberella zeae, Cytospora sp., Collectotrichum gloeosporioides, Alternaria solani, and Fusarium solani at concentration of 100 mg/L. Compound 4f and 4g exhibited significant activity against Alternaria solani and Collectotrichum gloeosporioides, respectively.

Griseofulvin Derivatives: Synthesis, Molecular Docking and Biological Evaluation

2019 ◽  
Vol 19 (13) ◽  
pp. 1145-1161 ◽  
Author(s):  
Victor Kartsev ◽  
Athina Geronikaki ◽  
Anthi Petrou ◽  
Boris Lichitsky ◽  
Marina Kostic ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Molecular Docking ◽  
Antifungal Activity ◽  
Organic Synthesis ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Design And Synthesis ◽  
Microdilution Method ◽  
New Compounds ◽  
Better Than

Background:Griseofulvin - a mold metabolite produced by Penisilium griseofulvum is known as an antifungal drug.Objective:Thus, the goal of this paper is the design and synthesis of new griseofulvin derivatives and evaluation of their antifungal activity.Methods:Forty-two new compounds were synthesized using classical methods of organic synthesis and evaluated for their antimicrobial activity by microdilution method.Results:All forty-two new compounds exhibited very good activity against eight tested micromycetes with MIC ranging from 0.0075-0.055 mg/ml and MFC from 0.02-024 mg/ml. All compounds exhibited better activity than reference drugs ketoconazole (7-42 times) and bifonazole (3-16 fold). The most promising was compound 15. The most sensitive fungal was found to be T. viride, while the most resistant, as was expected, was A. fumigatus. It should be mentioned that most of compounds exhibited better activity than griseofulvin.:The molecular docking studies revealed that the most active compound have the same hydrophobic and H-bonding interactions with Thr276 residue observed for griseofulvin forming 3 hydrogen bonds while griseofulvin only one. In general, the molecular docking results coincide with experimental.Conclusion:Forty-two giseofulvin derivatives were designed, synthesized and evaluated for antimicrobial activity. These derivatives revealed good antifungal activity, better than reference drugs ketoconazole, bifonazole, and griseofulvin as well.

scholarly journals Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 383
Author(s):  
Shan Yang ◽  
Tienan Wang ◽  
Yanan Zhou ◽  
Li Shi ◽  
Aidang Lu ◽  
...  
Keyword(s):  
Virus Assembly ◽  
Alternaria Solani ◽  
Phytopathogenic Fungi ◽  
Cercospora Arachidicola ◽  
Antifungal Activities ◽  
Inhibitory Rate ◽  
Commercial Plant ◽  
Protection Activity

Based on the structure of the natural product cysteine, a series of thiazolidine-4-carboxylic acids were designed and synthesized. All target compounds bearing thiazolidine-4-carboxylic acid were characterized by 1H-NMR, 13C-NMR, and HRMS techniques. The antiviral and antifungal activities of cysteine and its derivatives were evaluated in vitro and in vivo. The results of anti-TMV activity revealed that all compounds exhibited moderate to excellent activities against tobacco mosaic virus (TMV) at the concentration of 500 μg/mL. The compounds cysteine (1), 3–4, 7, 10, 13, 20,23, and 24 displayed higher anti-TMV activities than the commercial plant virucide ribavirin (inhibitory rate: 40, 40, and 38% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively), especially compound 3 (inhibitory rate: 51%, 47%, and 49% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively) with excellent antiviral activity emerged as a new antiviral candidate. Antiviral mechanism research by TEM exhibited that compound 3 could inhibit virus assembly by aggregated the 20S protein disk. Molecular docking results revealed that compound 3 with higher antiviral activities than that of compound 24 did show stronger interaction with TMV CP. Further fungicidal activity tests against 14 kinds of phytopathogenic fungi revealed that these cysteine derivatives displayed broad-spectrum fungicidal activities. Compound 16 exhibited higher antifungal activities against Cercospora arachidicola Hori and Alternaria solani than commercial fungicides carbendazim and chlorothalonil, which emerged as a new candidate for fungicidal research.

Discovery of novel obovatol-based phenazine analogs as potential antifungal agents: synthesis and biological evaluation in vitro

2021 ◽  
Vol 76 (3-4) ◽  
pp. 173-179
Author(s):  
Chun Yang ◽  
Lili Song ◽  
Zhong Miao ◽  
Lingyun Jiang ◽  
Ting Li ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Spore Germination ◽  
Plant Secondary Metabolites ◽  
Biological Evaluation ◽  
Phytopathogenic Fungi ◽  
Lead Compounds ◽  
Magnolia Obovata ◽  
Synthesis And Biological Evaluation ◽  
Positive Controls

Abstract To explore candidate fungicides from plant secondary metabolites, 16 novel obovatol-type phenazine derivatives were semi-synthesized from obovatol isolated from the leaves of Magnolia obovata Thunb. The antifungal activity of synthesized compounds was investigated in vitro against four phytopathogenic fungi using the spore germination method. The bioassay results showed that eight derivatives (8b, 8g, 8h–k, 8i′, and 8k′) exhibited better antifungal activity against Fusarium solani than two positive controls, especially compounds 8b (IC50 = 64.61 μg mL−1) and 8i′ (IC50 = 79.97 μg mL−1) showed pronounced inhibition of spore germination activity against F. solani. They could be used as lead compounds for further structural optimization. Additionally, the preliminary structure-activity relationships (SARs) illustrated that the introduction of a benzene ring monosubstituted with electron-withdrawing groups into the obovatol scaffold could lead to potentially antifungal compounds.

Synthesis and Antifungal Activities of 2-(N-Arylsulfonylindol-3-yl)-3-aryl-1,3-thiazinan-4-ones

2013 ◽  
Vol 68 (3-4) ◽  
pp. 77-81 ◽  
Author(s):  
Huan Qu ◽  
Rui Zhang ◽  
Ying Hu ◽  
Yazhen Ke ◽  
Zhinan Gao ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Fusarium Graminearum ◽  
Alternaria Alternata ◽  
Alternaria Solani ◽  
Phytopathogenic Fungi ◽  
Pyricularia Oryzae ◽  
Alternaria Brassicae ◽  
Antifungal Activities ◽  
Valsa Mali

4j A series of 2-(N-arylsulfonylindol-3-yl)-3-aryl-1,3-thiazinan-4-one derivatives were synthesized and evaluated in vitro against seven phytopathogenic fungi, namely Fusarium graminearum, Alternaria solani, Fusarium oxysporium f. sp. vasinfectum, Alternaria brassicae, Valsa mali, Alternaria alternata, and Pyricularia oryzae. Among all derivatives, especially compound exhibited a potential antifungal activity against four phytopathogenic fungi.

scholarly journals Synthesis, Antifungal Activity, 3D-QSAR, and Molecular Docking Study of Novel Menthol-Derived 1,2,4-Triazole-Thioether Compounds

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 6948
Author(s):  
Mei Huang ◽  
Wen-Gui Duan ◽  
Gui-Shan Lin ◽  
Bao-Yu Li
Keyword(s):  
Molecular Docking ◽  
Antifungal Activity ◽  
3D Qsar ◽  
Docking Study ◽  
Qsar Model ◽  
Gibberella Zeae ◽  
Cercospora Arachidicola ◽  
Molecular Docking Study ◽  
Qsar Analysis ◽  
Better Than

A series of novel menthol derivatives containing 1,2,4-triazole-thioether moiety were designed, synthesized, characterized structurally, and evaluated biologically to explore more potent natural product-based antifungal agents. The bioassay results revealed that at 50 μg/mL, some of the target compounds exhibited good inhibitory activity against the tested fungi, especially against Physalospora piricola. Compounds 5b (R = o-CH3 Ph), 5i (R = o-Cl Ph), 5v (R = m, p-OCH3 Ph) and 5x (R = α-furyl) had inhibition rates of 93.3%, 79.4%, and 79.4%, respectively, against P. piricola, much better than that of the positive control chlorothalonil. Compounds 5v (R = m, p-OCH3 Ph) and 5g (R = o-Cl Ph) held inhibition rates of 82.4% and 86.5% against Cercospora arachidicola and Gibberella zeae, respectively, much better than that of the commercial fungicide chlorothalonil. Compound 5b (R = o-CH3 Ph) displayed antifungal activity of 90.5% and 83.8%, respectively, against Colleterichum orbicalare and Fusarium oxysporum f. sp. cucumerinum. Compounds 5m (R = o-I Ph) had inhibition rates of 88.6%, 80.0%, and 88.0%, respectively, against F.oxysporum f. sp. cucumerinu, Bipolaris maydis and C. orbiculare. Furthermore, compound 5b (R = o-CH3 Ph) showed the best and broad-spectrum antifungal activity against all the tested fungi. To design more effective antifungal compounds against P. piricola, 3D-QSAR analysis was performed using the CoMFA method, and a reasonable 3D-QSAR model (r2 = 0.991, q2= 0.514) was established. The simulative binding pattern of the target compounds with cytochrome P450 14α-sterol demethylase (CYP51) was investigated by molecular docking.

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.

scholarly journals Vepris macrophylla (Baker) I. Verd Essential Oil: An Antifungal Agent against Phytopathogenic Fungi

2020 ◽  
Vol 21 (8) ◽  
pp. 2776 ◽  
Author(s):  
Laura Giamperi ◽  
Anahi Elena Ada Bucchini ◽  
Donata Ricci ◽  
Bruno Tirillini ◽  
Marcello Nicoletti ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Essential Oil ◽  
Antifungal Agent ◽  
Alternaria Solani ◽  
Phytopathogenic Fungi ◽  
Dilution Method ◽  
Agar Dilution Method ◽  
Fungistatic Activity ◽  
Leaf Essential Oil ◽  
Main Components

Rutaceae are widely used in ethnomedicine to treat infectious diseases in humans and plants. In this study, the antifungal activity of the Vepris macrophylla leaf essential oil (VEO) and its main components, citral and citronellol, was evaluated against six phytopathogenic fungi. In addition, the possible action of VEO on the synthesis of mycotoxins was evaluated as well. To determine the antifungal activity of VEO we used the agar dilution method and VEO showed inhibitory activity against all the tested fungi. In particular, VEO resulted to be fungicidal against Phytophthora cryptogea and Fusarium avenaceum. For all other fungi VEO exhibited fungistatic activity and the weakest effect was observed on Alternaria solani. Citral was very effective against P. cryptogea, F. avenaceum, F. poae and F. graminearum. On the other hand, citronellol showed good activity towards P. cryptogea and F. avenaceum and weaker activity towards F. poae and F. graminearum. It can be concluded that VEO can be considered a promising antifungal agent, especially against P. cryptogea and F. avenaceum, suggesting a possible use in the formulation of new selective and natural fungicides.

scholarly journals 5-(1H-Indol-3-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)alkancarboxylic Acids as Antimicrobial Agents: Synthesis, Biological Evaluation, and Molecular Docking Studies

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1964 ◽  
Author(s):  
Volodymyr Horishny ◽  
Victor Kartsev ◽  
Athina Geronikaki ◽  
Vasyl Matiychuk ◽  
Anthi Petrou ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Molecular Docking ◽  
Antifungal Activity ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Active Compounds ◽  
Molecular Docking Studies ◽  
Resistant Strains ◽  
Antibacterial And Antifungal ◽  
Better Than

Background: Infectious diseases symbolize a global consequential strain on public health security and impact on the socio-economic stability all over the world. The increasing resistance to the current antimicrobial treatment has resulted in crucial need for the discovery and development of novel entity for the infectious treatment with different modes of action that could target both sensitive and resistant strains. Methods: Compounds were synthesized using classical methods of organic synthesis. Results: All 20 synthesized compounds showed antibacterial activity against eight Gram-positive and Gram-negative bacterial species. It should be mentioned that all compounds exhibited better antibacterial potency than ampicillin against all bacteria tested. Furthermore, 18 compounds appeared to be more potent than streptomycin against Staphylococcus aureus, Enterobacter cloacae, Pseudomonas aeruginosa, Listeria monocytogenes, and Escherichia coli. Three the most active compounds 4h, 5b, and 5g appeared to be more potent against MRSA than ampicillin, while streptomycin did not show any bactericidal activity. All three compounds displayed better activity also against resistant strains P. aeruginosa and E. coli than ampicillin. Furthermore, all compounds were able to inhibit biofilm formation 2- to 4-times more than both reference drugs. Compounds were evaluated also for their antifungal activity against eight species. The evaluation revealed that all compounds exhibited antifungal activity better than the reference drugs bifonazole and ketoconazole. Molecular docking studies on antibacterial and antifungal targets were performed in order to elucidate the mechanism of antibacterial activity of synthesized compounds. Conclusion: All tested compounds showed good antibacterial and antifungal activity better than that of reference drugs and three the most active compounds could consider as lead compounds for the development of new more potent agents.

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