Synthesis and anti-phytopathogenic activity of 8-hydroxyquinoline derivatives

Yin, Xiaoyi; Sun, Yu; Lawoe, Raymond Kobla; Yang, Guan‐Zhou; Liu, Ying‐Qian; Shang, Xiaofei; Liu, Hua; Yang, Yu-Dong; Zhu, Jia-Kai; Huang, Xiaoling

doi:10.1039/c9ra05712a

Cited by 20 publications

(40 citation statements)

References 32 publications

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“…Pippi et al (2019a), found that this molecule's mechanism for action, possibly, takes place at the cell wall level, causing morphological changes in fungal cells. Similar results were obtained by Yin et al (2019), who observed the appearance of fungal cells treated with another 8HQ derivative pattern synthesized by the group. The effectiveness of PH 151 in controlling phytopathogenic fungi has been tested for the first time in this study.…”

Section: Discussionsupporting

confidence: 87%

“…Derivatives of 8HQ were synthesized and tested in vitro by Yin et al (2019). This highlighted compound 2, which was able to totally inhibit the mycelial growth of the five species of phytopathogenic fungi tested, at a concentration of 25 µg ml À1 .…”

Section: Discussionmentioning

confidence: 99%

“…Four repetitions per treatment were used. The percentages of inhibition, I (%), were determined using the formula: I (%) = ([(CÀd)À(TÀd)])/((CÀd)) 9 100, where d corresponds to the initial diameter of the colonies (5 mm), C to the diameter reached by the control and T to the final diameter reached of the fungus for each treatment (Agarwal et al 2001;Yin et al 2019).…”

Section: Mycelial Growthmentioning

confidence: 99%

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The efficacy of 8‐hydroxyquinoline derivatives in controlling the fungusIlyonectria liriodendri, the causative agent of black foot disease in grapevines

Souza

Chaves

Joaquim

et al. 2021

J of Applied Microbiology

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Aim: The purpose of this study was to evaluate the in vitro and in vivo efficiency of derivatives of 8-Hydroxyquinoline (8HQ) in controlling the fungus Ilyonectria liriodendri. Methods and Results: The in vitro tests consisted of assessing its susceptibility to the minimal inhibitory concentration (MIC) and the inhibition of mycelial growth. While the in vivo tests consisted of applying and assessing the most effective products for the protection of wounds, in both preventive + curative and curative forms. The MIC values for PH 151 (6Á25 µg ml À1 ) showed better results when compared to the fungicides tebuconazole (>50 µg ml À1 ) and mancozeb (12Á5 µg ml À1 for strain 176 and 25 µg ml À1 for strain 1117). PH 151 significantly inhibited mycelial growth, while mancozeb did not differ from the control. In in vivo tests, PH 151 again demonstrated excellent results in vitro, especially when applied preventively. Conclusions: The derivative of 8HQ PH 151 was effective in controlling the fungus I. liriodendri in vitro and proved to be a promising option for protecting wounds. Significance and Impact of the Study: This study points to the prospect of an effective and safe preventive antifungal product, which would enable the use of pesticides in vine culture to be reduced.

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Section: Discussionsupporting

confidence: 87%

Section: Discussionmentioning

confidence: 99%

Section: Mycelial Growthmentioning

confidence: 99%

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The efficacy of 8‐hydroxyquinoline derivatives in controlling the fungusIlyonectria liriodendri, the causative agent of black foot disease in grapevines

Souza

Chaves

Joaquim

et al. 2021

J of Applied Microbiology

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“…SEM observations were conducted according to the method of previous work with minor modifications [29,44]. Briefly, 5 mm diameter mycelial disks of F. oxysporum f.sp.…”

Section: Scanning Electron Microscope (Sem) Observationsmentioning

confidence: 99%

Design, Synthesis, Antibacterial, Antifungal and Anticancer Evaluations of Novel β-Pinene Quaternary Ammonium Salts

Zhang

Feng

Zhang

et al. 2021

IJMS

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β-pinene is a monoterpene isolated from turpentine oil and numerous other plants’ essential oils, which has a broad spectrum of biological activities. In the current work, six novel β-pinene quaternary ammonium (β-PQA) salts were synthesized and evaluated in vitro for their antifungal, antibacterial and anticancer activities. The in vitro assay results revealed that compounds 4a and 4b presented remarkable antimicrobial activity against the tested fungi and bacteria. In particular, compound 4a showed excellent activities against F. oxysporum f.sp. niveum, P. nicotianae var.nicotianae, R. solani, D. pinea and Fusicoccumaesculi, with EC50 values of 4.50, 10.92, 9.45, 10.82 and 6.34 μg/mL, respectively. Moreover, compound 4a showed the best antibacterial action against E. coli, P. aeruginosa, S. aureus and B. subtilis, with MIC at 2.5, 0.625, 1.25 and 1.25 μg/mL, respectively. The anticancer activity results demonstrated that compounds 4a, 4b, 4c and 4f exhibited remarkable activity against HCT-116 and MCF-7 cell lines, with IC50 values ranged from 1.10 to 25.54 μM. Notably, the compound 4c displayed the strongest cytotoxicity against HCT-116 and MCF-7 cell lines, with the IC50 values of 1.10 and 2.46 μM, respectively. Furthermore, preliminary antimicrobial mechanistic studies revealed that compound 4a might cause mycelium abnormalities of microbial, cell membrane permeability changes and inhibition of the activity of ATP. Altogether, these findings open interesting perspectives to the application of β-PQA salts as a novel leading structure for the development of effective antimicrobial and anticancer agents.

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“…Natural and synthetic quinoline nucleus containing compounds endowed a broad spectrum of biological activities [7,8]. Quinoline derivatives displayed vital pharmacological activities such as antimalarial [9,10], antimicrobial [11,12], antifungal [13,14], antitubercular [15,16], anticancer [17,18], antiviral [19,20], antiinflammatory and COX inhibitors [21,22], carbonic anhydrase inhibitors [23], antileishmanial [24], PIM inhibitors [25], anticonvulsant, and antihypertensive [26] activities. Thiazole is the important scaffold of several bioactive natural products [27,28] and reported broad spectrum of biological activity such as antibacterial [29,30], inflammatory [31], antifungal [32,33], antitubercular [34,35], antimalarial [36], anticancer [37], antiviral [38], and CNS active agents [39].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel 4‐(6‐substituted quinolin‐4‐yl)‐N‐aryl thiazol‐2‐amine derivatives as potential antimicrobial agents

Thakare

Shinde

Dakhane

et al. 2021

Journal of Heterocyclic Chem

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Cyclocondensation reaction of 4‐(2‐bromoacetyl)quinolin‐1‐ium bromide (4a–d) with substituted arylthiourea, (5a–g) afforded 4‐(6‐substituted quinolin‐4‐yl)‐N‐aryl/pyridyl thiazol‐2‐amine (6a‐ab). These newly synthesized derivatives were evaluated for in vitro antibacterial activity against Escherichia coli (NCIM 2574), Proteus mirabilis (NCIM 2388) (Gram‐negative strains), Bacillus subtilis (NCIM 2063), Staphylococcus albus (NCIM 2178) (Gram‐positive strains) and in vitro antifungal activity against Aspergillus niger (ATCC 504) and Candida albicans (NCIM 3100). Compounds 6a, 6b, 6d, 6f, 6k, and 6l showed moderate to good antibacterial activity against S. albus. Ten derivatives 6c, 6q, 6r, 6s, 6t, 6v, 6w, 6x, 6y, and 6aa, showed moderate to good activity against A. niger. N‐[4‐(Quinolin‐4‐yl)‐1,3‐thiazol‐2‐yl]pyridin‐2‐amine presented comparable activity against A. niger with respect to standard drug Rouconazole.

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Synthesis and anti-phytopathogenic activity of 8-hydroxyquinoline derivatives

Abstract: Phytopathogenic fungi have become a serious threat to the quality of agricultural products, food security and human health globally, necessitating the need to discover new antifungal agents with de novo chemical scaffolds and high efficiency.

Cited by 20 publications

References 32 publications

The efficacy of 8‐hydroxyquinoline derivatives in controlling the fungusIlyonectria liriodendri, the causative agent of black foot disease in grapevines

The efficacy of 8‐hydroxyquinoline derivatives in controlling the fungusIlyonectria liriodendri, the causative agent of black foot disease in grapevines

Design, Synthesis, Antibacterial, Antifungal and Anticancer Evaluations of Novel β-Pinene Quaternary Ammonium Salts

Synthesis and biological evaluation of novel 4‐(6‐substituted quinolin‐4‐yl)‐N‐aryl thiazol‐2‐amine derivatives as potential antimicrobial agents

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