Synthesis and Antimicrobial Activity of Norbornene-Containing Mannich Bases

Mammadbayli, E. H.; Hajiyeva, G.E.; Ibrahimli, S. I.; Cafarova, N. A.

doi:10.1134/s1070427219080160

Cited by 6 publications

(5 citation statements)

References 6 publications

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“…Scheme 4 -Aminoalkylated-2-naphthols 7-30 2-Naphthol 1 was amino alkylated in the Mannich reaction using 2-carboxaldehyde thiophene as the aldehyde reagent and 1H-benzotriazole as the amine reagent (Scheme 5). The antibacterial action of this new group of Mannich reactions [31][32][33][34][35][36][37][38] versus the original list of bacteria showed that they were all passive against gram-negative bacteria but active against gram-positive bacteria at varying stages. Candidates 34 and 38, which have hydrophobic moieties in this part of the molecule, are inert against E. fecalis, suggesting that the nature of the various amino moieties in the structure of these Mannich bases induces some selectivity.…”

Section: Figure 1: Structures Of Compounds 6a-6ementioning

confidence: 99%

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Mannich Bases: Synthesis, Pharmacological Activity, and Applications: A Review

Sadiq

2022

Iraqi Journal of Science

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The Mannich reaction is one of the most important types of organic chemistry fundamental reactions. It is a crucial stage in the production of various medicines, natural goods, and industrial chemicals. Chemists' imaginations have always been piqued because of this. In general, the Mannich reactions can be used as part of a tandem reaction sequence to produce complex target molecules in an elegant and often easy manner. The following article examines and summarizes methods for synthesizing Mannich derivatives, in addition to offering a survey of recent advancements in several fields’ applications of the Mannich reaction, such as biological applications, antimicrobial activity, anticancer activity, anti-inflammation and antioxidant activity, antimalarial activity, anti-viral activity, and so on. We also go over how mannich base is used in industry and agriculture.

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Section: Figure 1: Structures Of Compounds 6a-6ementioning

confidence: 99%

“…The compounds' lowest inhibitory and bactericidal concentrations were specified. At very low concentrations, the chemicals are effective against bacteria and fungi (S. aureus, E. coli, and C. albicans) [38].…”

Section: Scheme 6 -A Graphic Representation Of the Produced Title Com...mentioning

confidence: 99%

Mannich Bases: Synthesis, Pharmacological Activity, and Applications: A Review

Sadiq

2022

Iraqi Journal of Science

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“…Mammadbayli et al . have designed and synthesized a series of norbornene‐containing mannich bases, some of which showed notable antibacterial and antifungal activities toward several fungal pathogens [28] …”

Section: Introductionmentioning

confidence: 99%

“…[27] Mammadbayli et al have designed and synthesized a series of norbornene-containing mannich bases, some of which showed notable antibacterial and antifungal activities toward several fungal pathogens. [28] Carboxamide derivatives have obtained increasing concerns of pesticide chemists because of their broad antifungal spectra. [29] The amide groups widely exist in many commercial fungicides as vital pharmacophores, such as fluopyram [30] and pydiflumetofen (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antifungal Activity of Norbornene Carboxamide/sulfonamide Derivatives as Potential Fungicides Targeting Laccase

Yang,

Qiu,

Jin

et al. 2024

Chemistry & Biodiversity

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To explore more potential fungicides with new scaffolds, thirty‐seven norbornene carboxamide/sulfonamide derivatives were designed, synthesized, and assayed for inhibitory activity against six plant pathogenic fungi and oomycetes. The preliminary antifungal assay suggested that the title derivatives showed moderate to good antifungal activity against six plant pathogens. Especially, compound 6e presented excellent in vitro antifungal activity against Sclerotinia sclerotiorum (EC50 = 0.71 mg/L), which was substantially stronger than pydiflumetofen. In vivo antifungal assay indicated 6e displayed prominent protective and curative effects on rape leaves infected by S. sclerotiorum. The preliminary mechanism research displayed that 6e could damage the surface morphology and inhibit the sclerotia formation of S. sclerotiorum. In addition, the in vitro enzyme inhibition bioassay indicated that 6e displayed pronounced laccase inhibition activity (IC50 = 0.63 μM), much stronger than positive control cysteine. Molecular docking elucidated the binding modes between 6e and laccase. The bioassay results and mechanism investigation demonstrated that this class of norbornene carboxamide/sulfonamide derivatives could be promising laccase inhibitors for novel fungicide development.

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“…[19][20][21] Furthermore, norbornene and related structures have drawn increasing attentions as non-aromatic and nonplanar motifs in drug design, in attempts to afford variations in the so-called 'flatland drugs'. 22 Many norbornene derivatives have been reported to exhibit a broad spectrum of biological activities, such as antibacterial, 23 antiviral, 24 anticancer, 25 anti-inflammatory 26 and anticholinergic activities. 27 Concerning fungicidal agents, two commercial fungicides benzovindiflupyr and isopyrazam containing the norbornene group displayed a broad spectrum of antifungal activity toward different pathogenic fungi on grains, vegetables and fruits.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, antifungal evaluation and mechanism study of novel norbornene derivatives as potential laccase inhibitors

Jin,

Yang,

Qiu

et al. 2024

Pest Management Science

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BACKGROUNDTo discover novel fungicide candidates, five series of novel norbornene hydrazide, bishydrazide, oxadiazole, carboxamide and acylthiourea derivatives (2a‐2 t, 3a‐3 f, 4a‐4 f, 5a‐5 f and 7a‐7 f) were designed, synthesized and assayed for their antifungal activity toward seven representative plant fungal pathogens.RESULTSIn the in vitro antifungal assay, some title norbornene derivatives presented good antifungal activity against Botryosphaeria dothidea, Sclerotinia sclerotiorum and Fusarium graminearum. Especially, compound 2b exhibited the best inhibitory activity toward B. dothidea with the median effective concentration (EC50) of 0.17 mg/L, substantially stronger than those of the reference fungicides boscalid and carbendazim. The in vivo antifungal assay on apples revealed that 2b had significant curative and protective effects, both of which were superior to boscalid. In the preliminary antifungal mechanism study, 2b was able to injure the surface morphology of hyphae, destroy the cell membrane integrity and increase the intracellular reactive oxygen species (ROS) level of B. dothidea. In addition, 2b could considerably inhibit the laccase activity with the median inhibitory concentration (IC50) of 1.02 μM, much stronger than that of positive control cysteine (IC50 = 35.50 μM). The binding affinity and interaction mode of 2b with laccase were also confirmed by molecular docking.CONCLUSIONThis study presented a promising lead compound for the study on novel laccase inhibitors as fungicidal agrochemicals, which demonstrate significant anti‐B. dothidea activity and laccase inhibitory activity.This article is protected by copyright. All rights reserved.

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Synthesis and Antimicrobial Activity of Norbornene-Containing Mannich Bases

Cited by 6 publications

References 6 publications

Mannich Bases: Synthesis, Pharmacological Activity, and Applications: A Review

Mannich Bases: Synthesis, Pharmacological Activity, and Applications: A Review

Synthesis and Antifungal Activity of Norbornene Carboxamide/sulfonamide Derivatives as Potential Fungicides Targeting Laccase

Design, synthesis, antifungal evaluation and mechanism study of novel norbornene derivatives as potential laccase inhibitors

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