Synthesis and Antimicrobial Characteristics of Novel Biocides, 4,4'-(1,6-Hexamethylenedioxydicarbonyl)bis(1-alkylpyridinium iodide)s.

Maeda, Takuya; Manabe, Yuki; Yamamoto, Masashi; Yoshida, Minoru; Okazaki, K; Nagamune, Hideaki; Kourai, Hiroki

doi:10.1248/cpb.47.1020

Cited by 57 publications

(39 citation statements)

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“…It is known that phenolic compounds, in general, are capable of ionic dissociation (Mueller, 2001;Randhir et al, 2004), which makes possible to justify the antimicrobial activity of purified barbatic acid. The process of H + dissociation can lead to an acidification of plasmatic membrane surface of microorganism, resulting in H + -ATPase rupture that is required for ATP synthesis (Vattem et al, 2004;Maeda et al, 1999). Besides, it causes intracellular coagulation of cytoplasm constituents, leading the cell to death, or inhibiting its growth (Adham et al, 1998).…”

Section: Antimicrobial Assaysmentioning

confidence: 99%

Cladia aggregata (lichen) from Brazilian northeast: chemical characterization and antimicrobial activity

Martins¹,

Lima²,

Silva³

et al. 2010

Braz. arch. biol. technol.

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Section: Antimicrobial Assaysmentioning

confidence: 99%

Cladia aggregata (lichen) from Brazilian northeast: chemical characterization and antimicrobial activity

Martins¹,

Lima²,

Silva³

et al. 2010

Braz. arch. biol. technol.

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“…Thus, diverse articles focused on searching novel geminis with antibacterial and antifungal properties have lately been reported in the literature [11][12][13][14] . Some contributions in this connection involve gemini compounds having new active moieties, such as heteroatoms 15,16) , aromatic and non-aromatic cyclic substituents 17,18) , or perfluorinated chains [19][20][21][22][23] , among others. Nevertheless, it still remains an ample research area for synthesizing improved geminis efficiently and with low cost.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Surface-Active Properties, and Antimicrobial Activities of New Double-Chain Gemini Surfactants

et al. 2008

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A novel series of neutral and cationic dimeric surfactants were prepared involving ketalization reaction, Williamson etherification, and regioselective oxirane ring opening with primary and tertiary alkyl amines. The critical micelle concentration (CMC), effectiveness of surface tension reduction (g CMC ), surface excess concentration (G), and area per molecule at the interface (A) were determined and values indicate that the cationic series is characterized by good surface-active and self-aggregation properties. For the first time, we reported the antimicrobial activities against representative bacteria and fungi for dimeric compounds. The antimicrobial activity was found to be dependent on the target microorganism (Grampositive bacteria > fungi > Gram-negative bacteria), as well as both the neutral or ionic nature (cationic > neutral) and alkyl chain length (di-C 12 > di-C 18 > di-C 8 ) of the compounds. The cationic di-C 12 derivative was found to have equipotent activity to that of benzalkonium chloride (BAC) used as standard. Murguía, V.A. Vaillard, V.G. Sánchez et al. method, surface-active properties, and the antimicrobial activity of neutral and cationic series of new gemini compounds having a flexible, hydrophilic spacer and two alkyl chains of varying length. The molecular design and synthetic strategy were outlined to link the two hydrophilic head groups through a spacer having multiple oxygen atoms (1,3-dioxane ring, ether, and hydroxyl groups) conferring wettable properties. The structures of the synthesized compounds are illustrated in . EXPERIMENTAL PROCEDURES 1All the chemicals used in synthetic procedures were of reagent grade quality and used as received. 21 5 5 5 3 3 2 The reaction was carried out in a 100 mL three-neck round-bottomed flask equipped with a magnetic stirring bar and a Dean-Stark trap topped with a condenser 24,25) . A catalytic amount of p-toluenesulfonic acid monohydrate (5% w/w relative to the cyclohexanone) was added to a pentaerythritol (2.995 g, 22 mmol) and benzene-dimethylformamide (40 : 60) mixture (50 mL) at room temperature. The well-stirred dispersion was warmed to 80 until complete dissolution, and cyclohexanone (1.571 g, 15 mmol) was then added dropwise while the reaction mixture was heated to 115 for 48 hours. The water formed during the reaction was removed by distillation and collected in the Dean-Stark trap. The reaction was stopped when there was no further increase in the collected water. After cooling, the reaction mixture was poured into water (30 mL), neutralized with potassium carbonate and three-fold extracted with dichloromethane (30 mL). The organic layer was dried with MgSO 4 and evaporated in vacuo. After Kugelrohr distillation and column chromatography on silica gel by eluting with ether-light petroleum (80 : 20) mixture, the compound was obtained as a white solid in good yield (90 %) and good selectivity (92 %). (13), 173 (96), 160 (4), 125 (5), 101 (6), 99 (14), 83 (34), 71 (40), 55 (100), 41 (72) 26,27) . A 1 : 10 : 6 : 0.1 molar ...

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“…Compounds containing a pyridinium moiety attached to a heterocyclic system are important in natural product chemistry 1 and in organic synthesis 2, 3. Pyridinium salts have found use as acylating agents 4 , phase transfer catalysts 5 , biocides with a wide range of antimicrobial activity 6 , dyes 7 and cationic surfactants. The 1-alkylpyridinium salts, which are liquid at rt., so-called ionic liquids, are potential new solvents for synthesis and catalysis 8 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3-substituted pyridinium salts

Pernak¹,

Rogoza²

2000

Arkivoc

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Synthesis and Antimicrobial Characteristics of Novel Biocides, 4,4'-(1,6-Hexamethylenedioxydicarbonyl)bis(1-alkylpyridinium iodide)s.

Cited by 57 publications

References 0 publications

Cladia aggregata (lichen) from Brazilian northeast: chemical characterization and antimicrobial activity

Cladia aggregata (lichen) from Brazilian northeast: chemical characterization and antimicrobial activity

Synthesis, Surface-Active Properties, and Antimicrobial Activities of New Double-Chain Gemini Surfactants

Synthesis of 3-substituted pyridinium salts

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