Novel bis-crown ethers and their sodium complexes as antimicrobial agent: synthesis and spectroscopic characterizations

Hayvalı, Zeliha; Güler, Hüseyin; Öğütçü, Hatice; Sarı, Nurşen

doi:10.1007/s00044-014-0937-9

Cited by 16 publications

(9 citation statements)

References 25 publications

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“…The Schiff bases containing bis-benzo-15-crown-5 and their sodium derivatives were examined using a well diffusion method against bacterial strains; Staphylococcus aureus, Shigella dysenteria type 2, Listeria monocytogenes, Escherichia coli, Salmonella typhi H, Staphylococcus epidermis, Brucella abortus, Micrococcus luteus, Bacillus cereus, and Pseudomonas putida while choosing DMF as a control. The Schiff bases with 5-methoxy groups have shown maximum activity against strains with a concentration of 10 3 µM [54]. Interestingly, the chelates (12, 13 and 14) containing Na are found more potent against bacterial strains than bis-benzo-15-crown-5 compounds as shown in Figure 4.…”

Section: Antibacterial Potentialmentioning

confidence: 96%

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Heterocyclic Crown Ethers with Potential Biological and Pharmacological Properties: From Synthesis to Applications

et al. 2022

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Cyclic organic compounds with several ether linkages in their structure are of much concern in our daily life applications. Crown ethers (CEs) are generally heterocyclic and extremely versatile compounds exhibiting higher binding affinity. In recent years, due to their unique structure, crown ethers are widely used in drug delivery, solvent extraction, cosmetics manufacturing, material studies, catalysis, separation, and organic synthesis. Beyond their conventional place in chemistry, this review article summarizes the synthesis, biological, and potential pharmacological activities of CEs. We have emphasized the prospects of CEs as anticancer, anti-inflammatory, antibacterial, and antifungal agents and have explored their amyloid genesis inhibitory activity, electrochemical, and potential metric sensing properties. The central feature of these compounds is their ability to form selective and stable complexes with various organic and inorganic cations. Therefore, CEs can be used in gas chromatography as the stationary phase and are also valuable for cation chromatographic to determine and separate alkali and alkaline-earth cations.

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Section: Antibacterial Potentialmentioning

confidence: 96%

“…This reaction continued for 2 h at room temperature. The final product as bis-benzo-15-crown-5 ether was obtained and recrystallized from methanol as shown in Scheme 4 [54].…”

Section: Synthesis Of Bis-benzo-15-crown-5 Ethermentioning

confidence: 99%

Heterocyclic Crown Ethers with Potential Biological and Pharmacological Properties: From Synthesis to Applications

et al. 2022

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“…Crown ethers have been used for ion transport through bulk liquid membranes (3,4), as sensors and scaffolds for materials (5), and in the design of biologically active ionophores (6)(7)(8)(9)(10). The initial motivation in biology for developing synthetic ionophores was to create a new class of antibiotics inspired by many naturally occurring ionophoric antibiotics (5,8,(11)(12)(13)(14)(15)(16)(17)(18). Unfortunately, many of the potent ionophores developed in this context also proved highly toxic to mammalian cells (19,20).…”

Section: Introductionmentioning

confidence: 99%

Acylated and alkylated benzo(crown-ethers) form ion-dependent ion channels in biological membranes

Carrasquel-Ursulaez

Dehghany

Jones

et al. 2022

Biophysical Journal

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“…The exceptional property of these ethers to bind the alkali and alkaline earth metals had drawn considerable attention of the chemists, and since then, several crown ethers have been synthesized. [ 5–29 ] A significant number of these compounds have been synthesized by Charles Pedersen himself during that decade and after that. [ 1 ] One of the most important of these cyclic polyethers is the DB18C6.…”

Section: Introductionmentioning

confidence: 99%

Exploring the reaction pathway involved in the dibenzo‐18‐crown‐6 synthesis from catechol and bis(2‐chloroethyl) ether in presence of base

Sisodiya

Ali

Chattopadhyay

2021

J of Physical Organic Chem

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Computational investigations reported in this work have proposed the mechanism involved in the synthesis of dibenzo‐18‐crown‐6 (DB18C6) from catechol and bis(2‐chloroethyl) ether in presence of base. The transition states on the reaction path have been identified, and the corresponding barrier heights are estimated. Paths related to the side‐product formations, such as benzo‐9‐crown‐3 and 1,2‐bis[2‐(2‐chloroethoxy)ethoxy]‐benzene, have been also tracked. The cation‐assisted (Na+ and K+ ions) cyclization process (template effect) creates more structurally ordered reactant and transition state species. This facilitates the cyclization step that is an intramolecular SN2 process. Additionally, it eliminates possibilities of different side‐product formations giving better yield of the crown ether, as reported previously. This cyclization step has a comparatively lower barrier height for Na+ system (by 3 kcal/mol) in gas phase than K+ system; however, it becomes reverse in 1‐butanol where the barrier height is almost 2.5 kcal/mol lower during the K+DB18C6 formation. Consequently, a faster cyclization has been found in this solvent from the reaction rate studies for the potassium system. This is in‐line with the experimental observations reported on the alkali‐metal‐catalyzed benzo‐18‐crown‐6 ether formation reactions. The dipole moment value of the transition state involved in this step for the larger alkali metal ion system is found to be significantly higher (by 5–8 D) than the reactant species.

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Novel bis-crown ethers and their sodium complexes as antimicrobial agent: synthesis and spectroscopic characterizations

Cited by 16 publications

References 25 publications

Heterocyclic Crown Ethers with Potential Biological and Pharmacological Properties: From Synthesis to Applications

Heterocyclic Crown Ethers with Potential Biological and Pharmacological Properties: From Synthesis to Applications

Acylated and alkylated benzo(crown-ethers) form ion-dependent ion channels in biological membranes

Exploring the reaction pathway involved in the dibenzo‐18‐crown‐6 synthesis from catechol and bis(2‐chloroethyl) ether in presence of base

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