Synthesis and antibacterial activity of novel ethyl 2-alkoxyimino-2-benzimidazol-2-yl acetates bearing a morpholine group

Zhang, Peizhi; Wan, Fuxian; Liu, Ying; Li, Chengkun; Jiang, Lin

doi:10.1007/s11164-013-1437-0

Cited by 7 publications

(4 citation statements)

References 18 publications

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“…There are several examples in previously published papers in which the strategy described above was successfully applied by combining benzimidazole and morpholine pharmacophores on the same chemical structure; researchers have designed and synthesized many benzimidazole-morpholine compounds and investigate their pharmacological activities such as anticholinesterase [ 22 , 23 ], antimicrobial [ 24 , 25 , 26 ], antiinflammatory [ 27 , 28 , 29 , 30 ] and MAO inhibitory properties [ 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 ].…”

Section: Introductionmentioning

confidence: 99%

Pharmacological and Toxicological Screening of Novel Benzimidazole-Morpholine Derivatives as Dual-Acting Inhibitors

et al. 2017

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The aim of this study was to investigate acetylcholinesterase (AChE), monoamine oxidase A (MAO-A), monoamine oxidase B (MAO-B), cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) enzyme inhibitory, and antimicrobial activities of a new series of 2-(4-substituted phenyl)-1-[2-(morpholin-4-yl)ethyl]-1H-benzimidazole derivatives, for their possible use as multi-action therapeutic agents. Target compounds (n = 15) were synthesized under microwave irradiation conditions in two steps, and their structures were elucidated by FT-IR, 1H-NMR, 13C-NMR and high resolution mass spectroscopic analyses. Pharmacological screening studies revealed that two of the compounds (2b and 2j) have inhibitory potential on both COX-1 and COX-2 enzymes. In addition, cytotoxic and genotoxic properties of the compounds 2b, 2j and 2m were investigated via the well-known MTT and Ames tests, which revealed that the mentioned compounds are non-cytotoxic and non-genotoxic. As a concise conclusion, two novel compounds were characterized as potential candidates for treatment of frequently encountered inflammatory diseases.

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Section: Introductionmentioning

confidence: 99%

Pharmacological and Toxicological Screening of Novel Benzimidazole-Morpholine Derivatives as Dual-Acting Inhibitors

et al. 2017

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“…16 However, the thioether moiety in drug molecules might decrease the lipophilicity and increase the opportunity for hydrogen bond between drug and target enzyme, which is beneficial to enhance the affinity and improve the bioactivity. 20,21 With the encouragement of these results, and in an attempt to extend our previous study on the synthesis and antifungal activity of benzimidazole and pyrimidine derivatives, [22][23][24][25] we herein chose carbendazim as the lead compound, and replaced its carbamate group with phenylpyrimidine moiety and introduced a thioacetamide motif to the pyrimidine ring at the same time. Thus, a series of benzimidazole derivatives bearing pyrimidine and thioether moieties were designed and synthesized (Fig.…”

Section: Dokla Et Al Prepared N-(3-(1-(4-methylbenzyl)-mentioning

confidence: 98%

Synthesis and fungicidal activity of novel benzimidazole derivatives bearing pyrimidine‐thioether moiety against Botrytis cinerea

Sun

Zhang

Qian

et al. 2021

Pest Management Science

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BACKGROUND: Botrytis cinerea is a serious plant fungus and strongly affects the yield and quality of crops. The main control strategy is the employment of fungicides. To research for efficient fungicide with novel structure, a series of novel benzimidazole derivatives bearing pyrimidine and thioether moieties were designed and synthesized.RESULTS: Some target compounds such as 4h, 4i, 4k, 4l, 4m, 4s, 4t and 4u exhibited notable fungicidal activities, with half maximal effective concentration (EC 50 ) values in the range 0.13-0.24 ∼g mL −1 , which means that their activities were comparable or higher than that of carbendazim (EC 50 = 0.21 ∼g mL −1 ). Among them, N-(4-fluorophenyl)-2-((4-(1H-benzimidazol-2-yl)-6-(4-methoxyphenyl) pyrimidin-2-yl)thio)acetamide (4m) displayed the best activity (EC 50 = 0.13 ∼g mL −1 ). Molecular electrostatic potential analysis of 4m elucidated that the NH moiety of benzimidazole ring was located in the positive potential region and may generate hydrogen bond with target amino acid residue. Molecular docking analysis revealed that there was one hydrogen bond and one π-π interaction between 4m and target protein.CONCLUSIONS: This study demonstrated that the benzimidazole derivatives bearing pyrimidine and thioether moieties can be further optimized as a lead compound for the control of B. cinerea. The combination of molecular electrostatic potential and molecular docking analyses may provide a valuable reference for studying the interaction between the ligand and target protein.

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“…The morpholine structure forms an electron-deficient heterocycle due to the existence of oxygen atoms, which not only easily forms hydrogen bonds with target proteins, but also may participate in hydrophobic interactions [20,21]. Morpholine derivatives also have broad-spectrum biological activities, such as, antibacterial [22,23], anticancer [24], antioxidative [25], antiinflammatory [26], fungicidal [27], and anti-plant virus activities [28]. Fenpropimorph, dimethomrph, and flumorph (Figure 1) are morpholine fungicides, mainly used to control powdery mildew and rust of vegetables and fruits [29,30].…”

Section: Introductionmentioning

confidence: 99%

Research progress of piperazine and morpholine derivatives in the discovery of agricultural chemicals

Zhang

Xing

Zou

et al. 2023

Journal of Heterocyclic Chem

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Piperazine and morpholine are important heterocyclic structures, which are widely used in the discovery of agrochemicals. Piperazine and morpholine rings are often used as active substructures or bridges to design and synthesize new agrochemicals. In the past decade, piperazine and morpholine compounds have made rapid progress in the research and development of new pesticides, especially in the discovery of fungicides and antibacterial agents. In the future, more piperazine and morpholine pesticides may be commercialized. However, there is no comprehensive review on the use of piperazine and morpholine derivatives in the creation of new agrochemicals. Therefore, we systematically reviewed the application of piperazine and morpholine active compounds in the creation of new pesticides in the past 12 years. This paper not only summarizes the biological activities of piperazine and morpholine compounds, but also discusses the structure–activity relationship, physiological and biochemical changes, and mechanism of action. This work aims to provide inspiration and ideas for the discovery of new agrochemicals of piperazine and morpholine.

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Synthesis and antibacterial activity of novel ethyl 2-alkoxyimino-2-benzimidazol-2-yl acetates bearing a morpholine group

Cited by 7 publications

References 18 publications

Pharmacological and Toxicological Screening of Novel Benzimidazole-Morpholine Derivatives as Dual-Acting Inhibitors

Pharmacological and Toxicological Screening of Novel Benzimidazole-Morpholine Derivatives as Dual-Acting Inhibitors

Synthesis and fungicidal activity of novel benzimidazole derivatives bearing pyrimidine‐thioether moiety against Botrytis cinerea

Research progress of piperazine and morpholine derivatives in the discovery of agricultural chemicals

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