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 Synthesis of Bioactive Compounds from 3-Carene (II): Synthesis, Antifungal Activity and 3D-QSAR Study of (Z)- and (E)-3-Caren-5-One Oxime Sulfonates

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 477 ◽  
Author(s):  
Guo-Qiang Kang ◽  
Wen-Gui Duan ◽  
Gui-Shan Lin ◽  
You-Pei Yu ◽  
Xiao-Yu Wang ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Three Dimensional ◽  
Alternaria Solani ◽  
3D Qsar ◽  
Qsar Model ◽  
Quantitative Structure Activity Relationship ◽  
Cercospora Arachidicola ◽  
Qsar Study ◽  
In Vitro Antifungal Activity

A series of novel (Z)- and (E)-3-caren-5-one oxime sulfonates were designed and synthesized in search of potent antifungal agents. The structures of the intermediates and target compounds were confirmed by UV-Vis, FTIR, NMR, and ESI-MS. The in vitro antifungal activity of the target compounds was preliminarily evaluated against Cercospora arachidicola, Physalospora piricola, Alternaria solani, Rhizoeotnia solani, Bipolaris maydis and Colleterichum orbicalare at 50 µg/mL. The bioassay results indicated that the target compounds exhibited the best antifungal activity against P. piricola, in which compounds 4b, 4f, 4m, 4e, 4j, 4l, 4y, 4d, and 4p had excellent inhibition rates of 100%, 100%, 100%, 92.9%, 92.9%, 92.9%, 92.9%, 85.7%, and 85.7%, respectively, showing much better antifungal activity than that of the commercial fungicide chlorothanil. Both the compounds 4y and 4x displayed outstanding antifungal activity of 100% against B. myadis, and the former also displayed outstanding antifungal activity of 100% against R. solani. In order to design more effective antifungal compounds against P. piricola, the analysis of three-dimensional quantitative structure-activity relationship (3D-QSAR) was carried out using the CoMFA method, and a reasonable and effective 3D-QSAR model (r2 = 0.990, q2 = 0.569) has been established.

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 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.

scholarly journals Synthesis, 3D-QSAR and Molecular Docking Study of Nopol-Based 1,2,4-Triazole-Thioether Compounds as Potential Antifungal Agents

2021 ◽  
Vol 9 ◽  
Author(s):  
Xiu Wang ◽  
Wengui Duan ◽  
Guishan Lin ◽  
Baoyu Li ◽  
Ming Chen ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Antifungal Activity ◽  
Plant Pathogens ◽  
3D Qsar ◽  
Docking Study ◽  
Qsar Model ◽  
Molecular Docking Study ◽  
Activity Data ◽  
Target Enzyme

Cytochrome bc1 complex is an important component of cellular respiratory chain, and it is also an important target enzyme to inhibit the growth of plant pathogens. Using cytochrome bc1 complex as the target enzyme, twenty-three novel nopol-based 1,2,4-triazole-thioether compounds were designed and synthesized from natural preponderant resource β-pinene, and their structures were confirmed by FT-IR, NMR, ESI-MS and elemental analysis. The in vitro antifungal activity of the target compounds 5a-5w was preliminarily evaluated against eight plant pathogens at the concentration of 50 µg/ml. The bioassay results showed that the target compounds exhibited the best antifungal activity against Physalospora piricola, in which compounds 5b (R= o-CH3 Ph), 5e (R= o-OCH3 Ph), 5h (R= o-F Ph), 5m (R= o-Br Ph), 5o (R= m,m-OCH3 Ph), and 5r (R= p-OH Ph) had inhibition rates of 91.4, 83.3, 86.7, 83.8, 91.4 and 87.3%, respectively, much better than that of the positive control chlorothalonil. Also, compound 5a (R= Ph) had inhibition rate of 87.9% against Rhizoeotnia solani, and compound 5b (R= o-CH3 Ph) had inhibition rates of 87.6 and 89% against Bipolaris maydis and Colleterichum orbicala, respectively. In order to develop novel and promising antifungal compounds against P. piricola, the analysis of three-dimensional quantitative structure-activity relationship (3D-QSAR) was carried out using the CoMFA method on the basis of their antifungal activity data, and a reasonable and effective 3D-QSAR model (r2 = 0.944, q2 = 0.685) has been established. In addition, the theoretical study of molecular docking revealed that the target compounds could bind to and interact with the site of cytochrome bc1 complex.

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.

Design, synthesis, antifungal activity and 3D-QSAR study of novel pyrazole carboxamide and niacinamide derivatives containing benzimidazole moiety

2019 ◽  
Vol 43 (7) ◽  
pp. 3000-3010 ◽  
Author(s):  
Wei-Jie Si ◽  
Xiao-Bin Wang ◽  
Min Chen ◽  
Meng-Qi Wang ◽  
Ai-Min Lu ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Predictive Ability ◽  
3D Qsar ◽  
Qsar Model ◽  
Qsar Study ◽  
Design Synthesis ◽  
Effective Inhibition

The synthesized pyrazole carboxamide and niacinamide derivatives containing a benzimidazole moiety showed effective inhibition of the fungus B. cinereal growth. The 3D-QSAR model was built and revealed fine predictive ability.

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 Quantitative Structure–Activity Relationships of Natural-Product-Inspired, Aminoalkyl-Substituted 1-Benzopyrans as Novel Antiplasmodial Agents

Molecules ◽  
2021 ◽  
Vol 26 (17) ◽  
pp. 5249
Author(s):  
Friederike M. Wunsch ◽  
Bernhard Wünsch ◽  
Freddy A. Bernal ◽  
Thomas J. Schmidt
Keyword(s):  
3D Qsar ◽  
Structure Activity Relationship ◽  
Structural Features ◽  
Field Analysis ◽  
Activity Relationship ◽  
Quantitative Structure ◽  
Qsar Study ◽  
Activity Data ◽  
Structure Activity

On the basis of the finding that various aminoalkyl-substituted chromene and chromane derivatives possess strong and highly selective in vitro bioactivity against Plasmodium falciparum, the pathogen responsible for tropical malaria, we performed a structure–activity relationship study for such compounds. With structures and activity data of 52 congeneric compounds from our recent studies, we performed a three-dimensional quantitative structure–activity relationship (3D-QSAR) study using the comparative molecular field analysis (CoMFA) approach as implemented in the Open3DQSAR software. The resulting model displayed excellent internal and good external predictive power as well as good robustness. Besides insights into the molecular interactions and structural features influencing the antiplasmodial activity, this model now provides the possibility to predict the activity of further untested compounds to guide our further synthetic efforts to develop even more potent antiplasmodial chromenes/chromanes.

scholarly journals Synthesis, Biological Evaluation, and Molecular Modeling Studies of Chiral Chloroquine Analogues as Antimalarial Agents

2018 ◽  
Vol 62 (12) ◽  
Author(s):  
Srinivasarao Kondaparla ◽  
Utsab Debnath ◽  
Awakash Soni ◽  
Vasantha Rao Dola ◽  
Manish Sinha ◽  
...  
Keyword(s):  
Antimalarial Activity ◽  
3D Qsar ◽  
Biological Evaluation ◽  
Moderate Activity ◽  
Qsar Study ◽  
Antimalarial Agents ◽  
Structure Activity ◽  
New Findings

ABSTRACT In a focused exploration, we designed, synthesized, and biologically evaluated chiral conjugated new chloroquine (CQ) analogues with substituted piperazines as antimalarial agents. In vitro as well as in vivo studies revealed that compound 7c showed potent activity (in vitro 50% inhibitory concentration, 56.98 nM for strain 3D7 and 97.76 nM for strain K1; selectivity index in vivo [up to at a dose of 12.5 mg/kg of body weight], 3,510) as a new lead antimalarial agent. Other compounds (compounds 6b, 6d, 7d, 7h, 8c, 8d, 9a, and 9c) also showed moderate activity against a CQ-sensitive strain (3D7) and superior activity against a CQ-resistant strain (K1) of Plasmodium falciparum. Furthermore, we carried out docking and three-dimensional quantitative structure-activity relationship (3D-QSAR) studies of all in-house data sets (168 molecules) of chiral CQ analogues to explain the structure-activity relationships (SAR). Our new findings specify the significance of the H-bond interaction with the side chain of heme for biological activity. In addition, the 3D-QSAR study against the 3D7 strain indicated the favorable and unfavorable sites of CQ analogues for incorporating steric, hydrophobic, and electropositive groups to improve the antimalarial activity.

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