Synthesis and bioactivity of novel sulfone derivatives containing 2,4-dichlorophenyl substituted 1,3,4-oxadiazole/thiadiazole moiety as chitinase inhibitors

Xu, Wenya; Yang, Song; Bhadury, Pinaki S.; He, Jun; He, Ming; Gao, Lili; Hu, Deyu; Song, Baoan

doi:10.1016/j.pestbp.2011.05.006

Cited by 71 publications

(36 citation statements)

References 24 publications

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“…The nucleoside polyoxins and nikkomycins, the representative competitive CHS inhibitors 16 isolated from culture filtrates of Streptomyces strains, possess some of the structural features of the natural substrate UDP-GlcNAc and can interfere with the synthesis of fungal cell wall and ecdysis of insect in vivo by inhibiting the CHS. The inhibition constants (K i ) of nucleoside polyoxins are in range of 0.1-1 lM 17,18 . The low inhibitory activity and weak efficacy of these compounds maybe due to the degradation of their dipeptide side chains in the organism.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel 3-substituted amino-4-hydroxylcoumarin derivatives as chitin synthase inhibitors and antifungal agents

Chen

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of novel 3-substituted amino-4-hydroxycoumarin derivatives have been designed and synthesized as chitin synthase (CHS) inhibitors. All the synthesized compounds have been screened for their CHS inhibition activity and antimicrobial activity in vitro. The enzymatic assay indicated that most of the compounds have good inhibitory activity against CHS, in which compound 6o with IC 50 of 0.10 mmol/L had stronger activity than that of polyoxins B, which acts as control drug with IC 50 of 0.18 mmol/L. As far as the antifungal activity is concerned, most of the compounds possessed moderate to excellent activity against some representative pathogenic fungi. Especially, compound 6b was found to be the most potent agent against Cryptococcus neoformans with minimal inhibitory concentration (MIC) of 4 lg/mL. Moreover, the results of antibacterial screening showed that these compounds have negligible actions to some tested bacteria. Therefore, these compounds would be promising to develop selective antifungal agents.

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Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel 3-substituted amino-4-hydroxylcoumarin derivatives as chitin synthase inhibitors and antifungal agents

Chen

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…1,3,4-oxadiazole derivatives, another important heterocyclic derivative, has attracted more and more attention in development of fungicide, in the past few years, a lots of 1,3,4-oxadiazole derivatives with good antifungal activity have been developed by our group, some of the developed compounds processed good prospects for commercialization [19-24]. New fungicidal molecules are developed in the present work on the basis of the following: incorporation of the sub-structural unit of 1,3,4-oxadiazole into the backbone of boscalid and structural variation by the introduction of different kinds of moiety, resulting in nicotinamides containing a 1,3,4-oxadiazole substructure with broad-spectrum activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antifungal activities of novel nicotinamide derivatives containing 1,3,4-oxadiazole

Kang

Luo

et al. 2013

Chemistry Central Journal

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BackgroundPant diseases in agriculture are extremely difficult to control, which bring about for billions of dollars in economic losses worldwide each year; Nicotinamide derivatives has attracted more and more attention in the field of pesticide due to their broad bioactivities. In an effort to discover new molecules with good antifungal activity, a series of nicotinamide derivatives containing 1,3,4-oxadiazole were synthesized and bio-assayed.ResultsBioassays demonstrated that some of the title compounds exhibited favorable antifungal activities against Gibberella zeae, Fusarium oxysporum, and Cytospora mandshurica. compounds 7b, 7c, 8, 9a, 9b, and 9c displayed 46.4%, 39.6%, 53.0%, 43.2%, 58.3%, 45.6% activities against G. Zeae, respectively; the activities of compounds 7a, 7b, 8, 9a, 9b, and 9c against F. oxysporum were 55.2%, 51.1%, 58.9%, 63.2%, 53.3%, and 47.6%, respectively; whereas inhibitory rates of compounds 7a, 7b, 7c, 8, 9a, 9b, and 9c on C. mandshurica were 53.1%, 49.9%, 44.9%, 52.8%, 59.8%, 54.5%, and 49.3%, respectively.ConclusionA series of the novel nicotinamide derivatives containing 1,3,4-oxadiazole were synthesized and bio-assayed. The results of antifungal tests revealed that the synthesized nicotinamide derivatives possessed weakly to moderately antifungal activities against G. zeae, F. oxysporum, and C. mandshurica. Most of the synthesized compounds exhibited similar activities as (or higher than) these of hymexozol on their corresponding fungus, and compounds 7a, 8, 9a, and 9b showed considerable prospects for further optimization. Primary structure-activity relationships revealed that the introduction of the groups of 4-chloro-6-methyl on benzene, the hydrazone group containing N,N-dimethylamino, and acetyl at -NH2 could enhance the antifungal activity.

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“…It has recently been shown that the 1,3,4-oxadiazole ring, one of the most important and well-known heterocyclic nuclei, exhibits a wide variety of pesticidal biological activities, including antibacterial, [7][8][9][10][11][12][13] antifungal, [14][15][16][17][18][19][20][21] antiviral, [21][22][23] insecticidal, [24][25][26][27] and herbicidal. 28,29 In addition, in 2005, Guimarães et al demonstrated that introduction of a 1,3,4-oxadiazole ring into target compounds could change their polarity, flexibility and metabolic stability, effectively enhancing their bioactivity.…”

Section: Introductionmentioning

confidence: 99%

Novel bisthioether derivatives containing a 1,3,4‐oxadiazole moiety: design, synthesis, antibacterial and nematocidal activities

Tian

Chen

et al. 2017

Pest Management Science

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Synthesis and bioactivity of novel sulfone derivatives containing 2,4-dichlorophenyl substituted 1,3,4-oxadiazole/thiadiazole moiety as chitinase inhibitors

Cited by 71 publications

References 24 publications

Synthesis and biological evaluation of novel 3-substituted amino-4-hydroxylcoumarin derivatives as chitin synthase inhibitors and antifungal agents

Synthesis and biological evaluation of novel 3-substituted amino-4-hydroxylcoumarin derivatives as chitin synthase inhibitors and antifungal agents

Synthesis and antifungal activities of novel nicotinamide derivatives containing 1,3,4-oxadiazole

Novel bisthioether derivatives containing a 1,3,4‐oxadiazole moiety: design, synthesis, antibacterial and nematocidal activities

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