Efficient click chemistry towards novel 1H-1,2,3-triazole-tethered 4H-chromene−d-glucose conjugates: Design, synthesis and evaluation of in vitro antibacterial, MRSA and antifungal activities

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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Design, synthesis and antifungal activities in vitro of novel tetralin compounds

Chinese Chemical Letters ◽

10.1016/j.cclet.2007.12.031 ◽

2008 ◽

Vol 19 (3) ◽

pp. 264-268 ◽

Cited By ~ 1

Author(s):

Hui Tang ◽

You Jun Zhou ◽

Yao Wu Li ◽

Jia Guo Lv ◽

Can Hui Zheng ◽

...

Keyword(s):

Design Synthesis ◽

Antifungal Activities

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Novel galbonolide derivatives as IPC synthase inhibitors: design, synthesis and in vitro antifungal activities

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2003.09.072 ◽

2004 ◽

Vol 14 (1) ◽

pp. 143-145 ◽

Cited By ~ 10

Author(s):

Hiroki Sakoh ◽

Yuichi Sugimoto ◽

Hideaki Imamura ◽

Shunji Sakuraba ◽

Hideki Jona ◽

...

Keyword(s):

Design Synthesis ◽

Antifungal Activities

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Design, Synthesis, and Bioactivity Evaluation of New Thiochromanone Derivatives Containing a Carboxamide Moiety

Molecules ◽

10.3390/molecules26154391 ◽

2021 ◽

Vol 26 (15) ◽

pp. 4391

Author(s):

Lingling Xiao ◽

Lu Yu ◽

Pei Li ◽

Jiyan Chi ◽

Zhangfei Tang ◽

...

Keyword(s):

Antibacterial Activities ◽

Xanthomonas Oryzae ◽

Design Synthesis ◽

Compound A ◽

Antifungal Activities ◽

Antibacterial And Antifungal Activities ◽

In Vitro Antibacterial Activity ◽

Antibacterial And Antifungal ◽

In Vitro Antifungal Activity

In this study, using the botanical active component thiochromanone as the lead compound, a total of 32 new thiochromanone derivatives containing a carboxamide moiety were designed and synthesized and their in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas oryzae pv. oryzicolaby (Xoc), and Xanthomonas axonopodis pv. citri (Xac) were determined, as well as their in vitro antifungal activities against Botryosphaeria dothidea (B. dothidea), Phomopsis sp., and Botrytis cinerea (B. cinerea). Bioassay results demonstrated that some of the target compounds exhibited moderate to good in vitro antibacterial and antifungal activities. In particular, compound 4e revealed excellent in vitro antibacterial activity against Xoo, Xoc, and Xac, and its EC50 values of 15, 19, and 23 μg/mL, respectively, were superior to those of Bismerthiazol and Thiodiazole copper. Meanwhile, compound 3b revealed moderate in vitro antifungal activity against B. dothidea at 50 μg/mL, and the inhibition rate reached 88%, which was even better than that of Pyrimethanil, however, lower than that of Carbendazim. To the best of our knowledge, this is the first report on the antibacterial and antifungal activities of this series of novel thiochromanone derivatives containing a carboxamide moiety.

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Design, synthesis and in vitro antibacterial and antifungal activities of some novel spiro[azetidine-2,3′-indole]-2,4(1′H)-dione

Medicinal Chemistry Research ◽

10.1007/s00044-010-9354-x ◽

2010 ◽

Vol 20 (5) ◽

pp. 587-594 ◽

Cited By ~ 12

Author(s):

Ravi J. Shah ◽

Neha R. Modi ◽

Manish J. Patel ◽

Laxmanbhai J. Patel ◽

Bhupendrasinh F. Chauhan ◽

...

Keyword(s):

Design Synthesis ◽

Antifungal Activities ◽

Antibacterial And Antifungal Activities ◽

Antibacterial And Antifungal

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Design, Synthesis, and In Vitro and In Vivo Evaluation of Novel Fluconazole-Based Compounds with Promising Antifungal Activities

ACS Omega ◽

10.1021/acsomega.1c04016 ◽

2021 ◽

Author(s):

Mohammad Shafiei ◽

Hossein Toreyhi ◽

Loghman Firoozpour ◽

Tahmineh Akbarzadeh ◽

Mohsen Amini ◽

...

Keyword(s):

In Vivo Evaluation ◽

Design Synthesis ◽

Antifungal Activities

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

Molecules ◽

10.3390/molecules26020372 ◽

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.

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