Synthesis and characterization of novel simultaneous C and O-coordinated and nitrate-bridged complexes of silver(<scp>i</scp>) with carbonyl-stabilized sulfonium ylides and their antibacterial activities

Sabounchei, Seyyed Javad; Bagherjeri, Fateme Akhlaghi; Mozafari, Zeinab; Boskovic, Colette; Gable, Robert W.; Karamian, Roya; Asadbegy, Mostafa

doi:10.1039/c2dt31902k

Cited by 29 publications

(18 citation statements)

References 35 publications

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“…The complexation of sulfur ylides to various transition metals has been extensively studied [9,[11][12][13], however the synthesis, X-ray characterization, theoretical study and also application of a palladium complex of a sulfur ylide as a precursor in the Suzuki-Miyaura coupling reaction are the key advantages of this study. This paper includes the synthesis, spectroscopic and X-ray crystallographic characterization, theoretical study and application of new palladium(II) complex of an α-keto stabilized sulfur ylide in the Suzuki-Miyaura cross-coupling reaction.…”

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A new Pd(II) complex of a sulfur ylide; Synthesis, X-ray characterization, theoretical study and catalytic activity toward the Suzuki–Miyaura reaction

et al. 2016

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A new Pd(II) complex of a sulfur ylide; Synthesis, X-ray characterization, theoretical study and catalytic activity toward the Suzuki–Miyaura reaction

et al. 2016

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“…42) Briefly, the bacterial cells (10 5 CFU/mL) were added into 100 µL of the compounds dilutions in MullerHinton broth, and then incubated at 37°C for 24 h. The microbial growth was examined by visual inspection. In this assay, all compounds were dissolved in DMSO.…”

Section: Evaluation Of Antibacterial Activity In Vitromentioning

confidence: 99%

“…Pa was incubated in the presence of the Ag(I) complex 2h at 0, 1, 2, 4 and 8 times respective MIC (MIC=0.7 µM) and the number of surviving bacteria were determined by colony counting. The data are judged relative to the conventional definition of bactericidal activity, that is, a 3 log 10 CFU/mL or greater reduction in the initial inoculum by 24 h. 42,46) In growth curve studies (Fig. 3B), no influence was observed on the growth of Pa in liquid medium supplemented with up to 2 times the MIC of 2h.…”

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“…On the other hand, G(−) bacteria are more susceptible to the Ag(I) complex 2h and AgNO 3 than G(+) bacteria, presumably due to their thinner wall, which may allow more rapid absorption or adhesion of the silver into the cell. [43][44][45] The cell wall of G(−) bacteria contains lipopolysaccharide (LPS) as the outer leaflet of the outer membrane bilayer. However, the G(+) bacteria are surrounded by a thick peptidoglycan layer, which explains the elevated activity of the metal complex over G(−) bacteria than G(+) bacteria species.…”

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“…The minimum inhibitory concentrations (MIC, µM) were determined by means of standard serial dilution method according to the National Committee for Clinical Laboratory Standards (NCCLS) 42) and are presented in Table 3. Currently available antimicrobial drugs Kanamycin, Gentamicin, Linezolid, or Norfloxacin were used as the positive control.…”

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Synthesis and Antimicrobial Activity of 2-Trifluoroacetonylbenzoxazole Ligands and Their Metal Complexes

Watanabe

Sekiya

Tamai

et al. 2018

CHEMICAL & PHARMACEUTICAL BULLETIN

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Key words antibacterial activity; fluorinated benzoxazole; metal complex; trifluoroacetylBacterial infection remains a serious threat to human lives due to rapid development of resistance to the existing antibiotics. In order to prevent this major medical problem, the discovery of new types of antimicrobial agents is a very important but challenging task.1,2) Transition metal complexes have received great attention because many drugs such as antibiotics and quinolone antibiotics possess better pharmaceutical properties when they are in the form of metal complexes. 3-7)Benzoxazole heterocycle system is an important pharmacophore and privileged structure in the medicinal chemistry. 8-10)Its derivatives and particularly, 2-substituted benzoxazoles exert various biological activities such as antimicrobial, antiviral, antifungal, and anticancer. [11][12][13][14][15] In previous studies, we have identified 2-trifluoroacetonylbenzoxazole (1a) with in vitro antimicrobial activity against Helicobacter pylori and Escherichia coli (Ec) from our compound library of trifluoromethyl ketones obtained by our developed reactions. 16,17) The heteroaryl-substituted alkenol systems such as 1a are known to chelate some metal ions such as aluminum 18) and to form a stable six-membered metal complexes in a bidentate mode, where the complexes were reinforced by a positive inductive effect of the heterocyclic moiety and a negative inductive effect of the CF 3 groups. [19][20][21][22][23] In the light of these knowledge, three 2-fluoroacetonylbenzoxazole ligands 1a-c and their new Zn(II) complexes 2a-c have been synthesized in order to check how the metal ion binding may influence their antibacterial activity (Chart 1). In addition, syntheses of new metal [Mg(II), Ni(II), Cu(II), Pd(II), and Ag(I)] complexes 2d-h from 1a have been also described ( Table 1). The structures of six metal complexes 2b and 2d-h were determined by single-crystal X-ray diffraction analyses. In vitro antimicrobial activities of the ligands 1a-c and their metal complexes 2a-h were investigated against six Gram-positive (G(+)) and six Gram-negative (G(−)) bacteria and the results were compared with those of silver nitrate and appropriate antibiotics such as Kanamycin, Gentamicin, Norfloxacin, and/or Linezolid. The most potent Ag(I) complex 2h is bacteriostatic, disrupts membrane integrity observed by scanning electron microscopy (SEM) and is less likely to develop resistance development against Pseudomonas aeruginosa (Pa). Results and DiscussionChemistry First, three benzoxazole ligands 1a-c and their new Zn(II) complexes 2a-c have been prepared in order to investigate the relationship of the ligands and their Zn(II) complexes with their antibacterial activities.Our synthetic protocol to obtain the ligand 1a consists of a trifluoroacetylation of 2-methylbenzoxazole with trifluoroacetic anhydride (TFAA) in the presence of pyridine 24) (Chart 1). The Zn(II) complex 2a was prepared by the reaction of 1a with zinc dust in MeCN in 78% yield, consisting of 1a with zinc(...

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Dimethyl(2-oxo-2-phenylethyl)-sulfonium Inner Salt

Akagawa

2016

Encyclopedia of Reagents for Organic Synthesis

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Synthesis and characterization of novel simultaneous C and O-coordinated and nitrate-bridged complexes of silver(i) with carbonyl-stabilized sulfonium ylides and their antibacterial activities

Cited by 29 publications

References 35 publications

A new Pd(II) complex of a sulfur ylide; Synthesis, X-ray characterization, theoretical study and catalytic activity toward the Suzuki–Miyaura reaction

A new Pd(II) complex of a sulfur ylide; Synthesis, X-ray characterization, theoretical study and catalytic activity toward the Suzuki–Miyaura reaction

Synthesis and Antimicrobial Activity of 2-Trifluoroacetonylbenzoxazole Ligands and Their Metal Complexes

Dimethyl(2-oxo-2-phenylethyl)-sulfonium Inner Salt

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