Design, Synthesis and Bioactivity of N-Glycosyl-N'-(5-substituted phenyl-2-furoyl) Hydrazide Derivatives

Cui, Zi‐Ning; Su, Hang; Jiang, Jiazhen; Yang, Xinling; Nishida, Yoshihiro

doi:10.3390/ijms15046741

Cited by 12 publications

(8 citation statements)

References 30 publications

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“…It has been reported that the compounds containing furan showed broad-spectrum bioactivities. A wide range of derivatives such as dibenzoylureas 15 , diacylhydrazines 16 17 18 19 20 21 , acylhydrazones 22 23 24 25 , semicarbazide 26 , pyrazole, 1,2,4-triazole 27 , 1,3,4-oxadiazole 28 , and carbamic acid esters 29 30 containing 5-phenyl-2-furan moiety has been synthesized and studied in our group for the development of novel chemical entities as a lead molecule in drug and agrochemical discovery. All the compounds showed diverse and significant bioactivities such as fungicidal, insecticidal, and antitumor activities.…”

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confidence: 99%

Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4- thiadiazole derivatives containing 5-phenyl-2-furan

Cui

et al. 2016

Sci Rep

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A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized using Lawesson’s reagent by an efficient approach under microwave irradiation in good yields. Their structures were characterized by MS, IR, 1H NMR, 13C NMR, and elemental analysis. Their in vitro and in vivo fungicidal activities revealed that the title compounds exhibited considerable activity against five selected fungi, especially to Phytophthora infestans. In order to illustrate the mechanism of title compounds against P. infestans, scanning electron micrographs (SEM) and transmission electron micrographs (TEM) were applied. The morphological and ultrastructural studies demonstrated that compound I18 led to swelling of hyphae, thickening and proliferating multilayer cell walls, excessive septation and accumulation of dense bodies. The bioassay results indicated compound I18 might act on cell wall biosynthesis, and blocked the nutrition transportation and led to cells senescence and death. Meanwhile, compound I18 had broad fungicidal activity against other twenty different kinds of fungi. These results suggested that title compounds were eligible to be development candidates and compound I18 as a promising lead compound was worthy to be further discovery, especially against P. infestans.

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confidence: 99%

Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4- thiadiazole derivatives containing 5-phenyl-2-furan

Cui

et al. 2016

Sci Rep

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“…The outcome of coupling of acylhydrazines or thioacylhydrazines with various reducing saccharides has been reported to exist in solution as sugar hydrazones (acyclic forms) − or glycosylhydrazides (cyclic forms) − and often coexist in tautomeric equilibrium mixtures. ,,, The preference of adopting the open chain, cyclic structures, or an interconvertable equilibrated mixture of them has been synergistically effected by the basicity of hydrazines, reaction conditions, pH of the reaction mixture, solvent used in 1 H NMR spectra, as well as sugar configuration …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of 1,3,4-Oxadiazoline, 1,3-Thiazolidine, and 1,2,4-Triazoline Double-Tailed Acyclo C-Nucleosides

et al. 2022

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The condensation products of terphthaloyl bishydrazide with two equivalents of various monosaccharide aldoses were found to have a bis(sugarhydrazone) form or bis-glycosylhydrazide structure or coexist in tautomeric equilibrium depending on the sugar configuration. The condensation products were substantially utilized as 3-acetyl-1,3,4-oxadiazoline, 1,3-thiazolidine, and 4-amino-1,2,4-triazoline double-tailed acyclo C-nucleosides synthons. The preliminary antimicrobial activities of representative examples of the prepared compounds were evaluated.

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“…Hydrazides have been described as useful key compound to synthesize various heterocyclic compounds . Hydrazides are reported to have different and rich biological properties . Hydrazones are used in electrophotography, due to their relatively simple synthesis, low molecular weight, and aperture‐conveying properties .…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis, Antimicrobial, Antioxidant Assessments and Geometric Optimization Calculations of Azoles‐ Incorporating Quinoline Moiety

Hamama

Ibrahim

Gooda

et al. 2018

Journal of Heterocyclic Chem

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A novel series of Schiff bases, hydrazide, and hydrazine derivatives containing quinoline moiety were synthesized via condensation of 3-substituted quinolines 1a and 1b with different aromatic amines or hydrazines. Furthermore, various heterocyclic ring systems: 1,3,4-thiadiazole, thiazolidin-4-one, 2-thioxoimidazolidin-4-one, and thiazole derivatives 10-13 were synthesized by refluxing hydrazinecarbothioamide derivative 9 with different acetic acid derivatives. Theoretical calculation of the title compounds were carried out using density functional theory method. The geometrical optimization of the prepared target compounds was theoretically analyzed. The synthesized compounds were examined for their antimicrobial and antioxidant activities. The obtained results revealed clearly that compounds 8 and 13 displayed promising activity as an antimicrobial activity and compounds 3, 5, 6, 7, and 9 exhibited better radical scavenging ability. Scheme 3. Transformation reaction of thiosemicarbazone derivative 9 to quinolone-attached 5-membered heterocyclic moieties 10-13. Scheme 2. Reaction of 2-substituted quinoline-3-carbaldehyde 1a and 1b with hydrazine derivatives.

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Design, Synthesis and Bioactivity of N-Glycosyl-N'-(5-substituted phenyl-2-furoyl) Hydrazide Derivatives

Cited by 12 publications

References 30 publications

Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4- thiadiazole derivatives containing 5-phenyl-2-furan

Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4- thiadiazole derivatives containing 5-phenyl-2-furan

Synthesis and Antimicrobial Activity of 1,3,4-Oxadiazoline, 1,3-Thiazolidine, and 1,2,4-Triazoline Double-Tailed Acyclo C-Nucleosides

Efficient Synthesis, Antimicrobial, Antioxidant Assessments and Geometric Optimization Calculations of Azoles‐ Incorporating Quinoline Moiety

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