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.

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, antifungal evaluation, and molecular docking of novel 1,2,4-triazole derivatives containing oxime ether and cyclopropyl moieties as potential sterol demethylase inhibitors

2021 ◽  
Author(s):  
Sheng-Xin Sun ◽  
Jing-Hua Yan ◽  
Jiang-Tao Zuo ◽  
Xiao-Bin Wang ◽  
Min Chen ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Oxime Ether ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
Triazole Derivatives

A series of novel triazole derivatives containing oxime ether and cyclopropyl moieties were designed and synthesized. Some compounds exhibited remarkable antifungal activities. The molecular docking of compound 5k with FgCYP51 was investigated.

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.

scholarly journals Design, Synthesis and Biological Evaluation of Novel 1, 3, 4-Oxadiazole Bearing Pyridine Moiety

2019 ◽  
pp. 300-307
Author(s):  
Asma D. Ambekari ◽  
Shrinivas K. Mohite
Keyword(s):  
Antimicrobial Activity ◽  
Mass Spectra ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Pyridine Moiety ◽  
Anti Inflammatory ◽  
Physicochemical Data ◽  
Synthesis And Biological Evaluation

Series of novel substituted Synthesis of N-{[5-(substituted)-1,3,4-oxadiazole-2-yl] carbamothioyl} derivatives containing 1,3,4-oxadiazole moiety were synthesized by microwave as a green chemistry method and conventional method by using pyridine 3- carboxylic acid as a starting material. The structures of the synthesized compounds were characterized by physicochemical data, IR, Mass spectra and 1HNMR. All the newly synthesized compound screened for their antimicrobial and In-vivo and In-vitro Anti-inflammatory studies. Anti-inflammatory studies revealed that compound 4f showed significant in-vivo and in-vitro anti-inflammatory activity as well potent antimicrobial activity.

scholarly journals Design, synthesis, and in vitro antifungal evaluation of novel triazole derivatives bearing alkynyl side chains

2019 ◽  
Vol 23 (5) ◽  
pp. 576-585 ◽  
Author(s):  
Tingjunhong Ni ◽  
Lei Pang ◽  
Zhan Cai ◽  
Fei Xie ◽  
Zichao Ding ◽  
...  
Keyword(s):  
Side Chains ◽  
Design Synthesis ◽  
Triazole Derivatives

Design, synthesis and in vitro anti-tuberculosis activity of benzo[6,7]cyclohepta[1,2- b ]pyridine-1,2,3-triazole derivatives

2017 ◽  
Vol 27 (23) ◽  
pp. 5119-5121 ◽  
Author(s):  
Yasodakrishna Sajja ◽  
Sowmya Vanguru ◽  
Hanmanth Reddy Vulupala ◽  
Rajashaker Bantu ◽  
Perumal Yogeswari ◽  
...  
Keyword(s):  
Design Synthesis ◽  
Triazole Derivatives ◽  
Tuberculosis Activity

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).

2-Hydroxypropyl derivatives of 1,2,3-thiadiazole and 1,2,3-triazole: Synthesis and antifungal activity

2011 ◽  
Vol 83 (3) ◽  
pp. 715-722 ◽  
Author(s):  
Yury Morzherin ◽  
Polina E. Prokhorova ◽  
Dmitry A. Musikhin ◽  
Tatiana V. Glukhareva ◽  
Zhijin Fan
Keyword(s):  
Mass Spectrometry ◽  
Antifungal Activity ◽  
Ir Spectroscopy ◽  
Elemental Analysis ◽  
Antifungal Activities ◽  
Triazole Derivatives ◽  
New Compounds ◽  
Derivatives Of

A series of novel 5-(2-hydroxypropyl)amino-1,2,3-thiadiazole and 5-(2-hydroxy-propyl)sulfanyl-1,2,3-triazole derivatives were designed and synthesized as candidate fungicides. The new compounds were identified by NMR and IR spectroscopy, mass spectrometry, and elemental analysis. Their antifungal activities were evaluated.

scholarly journals Design, Synthesis, andIn VitroAntiplatelet Aggregation Activities of Ferulic Acid Derivatives

2015 ◽  
Vol 2015 ◽  
pp. 1-7 ◽  
Author(s):  
Peng-Xuan Zhang ◽  
Hang Lin ◽  
Cheng Qu ◽  
Yu-Ping Tang ◽  
Nian-Guang Li ◽  
...  
Keyword(s):  
Ferulic Acid ◽  
Target Compound ◽  
Design Synthesis ◽  
Antiplatelet Aggregation ◽  
Aggregation Activity ◽  
New Compounds

In order to discover new compounds with antiplatelet aggregation activities, some ferulic acid (FA) derivatives were designed and synthesized. Thein vitroantiplatelet aggregation activities of these compounds were assessed by turbidimetric test. The results showed that the target compound7fhad potent antiplatelet aggregation activity with its IC5027.6 μmol/L, and7fcan be regarded as a novel potent antiplatelet aggregation candidate.

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