Synthesis, characterization and antibacterial activity of some new ferrocenyl selenazoles and 3,5-diferrocenyl-1,2,4-selenadiazole

Al‐Rubaie, Ali Z.; Al-Jadaan, Shaker A. S.; Muslim, Salah Kadhim; Saeed, Eman A.; Ali, Eman T.; Al-Hasani, Amer K.J.; Al-Salman, Hussien N.K.; Al-Fadal, Sabaa A.M.

doi:10.1016/j.jorganchem.2014.10.007

Cited by 23 publications

(16 citation statements)

References 28 publications

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“…At the same time, the reaction of 1-cyanoferrocene 18 with sodiumhydrogenselenide, and subsequent treatment with Na 2 [PdCl 4 ], gave 3,5-diferrocenyl-1,2,4-selenadiazole 21. From a pharmacological point of view, interesting results were obtained against the Gram-negative Bacteria E. coli and Pseudomonas aeruginosa [13] (Table 2). The expression of efflux systems by bacteria is a key issue that the researchers should take into account when they try to tackle multidrug resistance, especially of Gramnegative ones.…”

Section: 3-selenazoles and Benzoisoselenazolones Derivativesmentioning

confidence: 99%

Synthetic Approaches to Organoselenium Derivatives with Antimicrobial and Anti-Biofilm Activity

Leo

Messina²,

Nascimento

et al. 2019

MROC

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In the recent years, an increasing attention has been given to the biological activities exerted by organoselenium compounds. In 1984, Sies reported for the first time the ability of ebselen to mimic the activity of glutathione peroxidase. From this milestone, several studies reported the pharmacological properties of selenium-containing compounds including their exploitation as antimicrobials. In this context, this minireview presents the most recent examples of seleno derivatives endowed with antimicrobial activities while discussing the most interesting and recent synthetic procedures used to obtain these compounds.

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Section: 3-selenazoles and Benzoisoselenazolones Derivativesmentioning

confidence: 99%

Synthetic Approaches to Organoselenium Derivatives with Antimicrobial and Anti-Biofilm Activity

Leo

Messina²,

Nascimento

et al. 2019

MROC

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“…In the recent years, selenium compounds have gained substantial interest not only for their importance in synthetic chemistry but also for their biological properties (Burling and Goldstein, 1992 ; Lobinski et al, 2000 ; Koketsu et al, 2002 ; Abdel-Hafez, 2008 ; Potewar et al, 2008 ; Abdel-Lattif et al, 2014 ; Al-Rubaie et al, 2014 ). Furthermore, the incorporation of selenium functionalities into organic scaffolds reported to permit alteration of their chemical and biological activities (Al-Smadi and Al-Momani, 2008 ).…”

Section: Introductionmentioning

confidence: 99%

Novel 2-Hydroselenonicotinonitriles and Selenopheno[2, 3-b]pyridines: Efficient Synthesis, Molecular Docking-DFT Modeling, and Antimicrobial Assessment

et al. 2021

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Selenium containing heterocyclic compounds gained great interest as bioactive molecules as of late. This report explores the design, synthesis, characterization, and antimicrobial screening of new pyridine derivatives endowed with selenium moieties. A one-pot multicomponent system with a solvent-free, microwave irradiation environment was employed to afford this series. The spectroscopic techniques were exploited to verify the structures of the synthesized derivatives. Additionally, the agar diffusion method was employed to determine the antimicrobial activity of all the desired compounds. Of all the synthesized molecules, 9b, 12b, 14f, and 16d exhibited well to remarkable antibacterial and antifungal activities. Moreover, derivative 14f demonstrated the most potent antibacterial and antifungal performance. The results were also supported by molecular docking studies, utilizing the MOE (molecular operating environment) which revealed the best binding mode with the highest energy interaction within the binding pocket. Lastly, theoretical DFT calculations were carried out in a gas phase at B3LYP 6-311G (d,p) basis set to predict the molecular geometries and chemical reactivity descriptors. DFT results have been used to illustrate that molecular docking findings and biological activity assessments.

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“…Application of organoselenium compounds is one of modern trends in bioorganic chemistry. Organoselenium compounds show wide spectrum of biological activities [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31]. Functionalized selenides containing benzenesulfonamide moieties were found to inhibit five human isoforms of zinc enzyme carbonic anhydrase.…”

Section: Introductionmentioning

confidence: 99%

Quantum Chemical and Experimental Studies of an Unprecedented Reaction Pathway of Nucleophilic Substitution of 2-Bromomethyl-1,3-thiaselenole with 1,3-Benzothiazole-2-thiol Proceeding Stepwise at Three Different Centers of Seleniranium Intermediates

et al. 2021

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The results of quantum chemical and experimental studies of the reaction of 2-bromomethyl-1,3-thiaselenole with 1,3-benzothiazole-2-thiol made it possible to discover the unprecedented pathway of this reaction, which proceeds stepwise at three different centers of seleniranium intermediates. The first stage includes an attack of thiolate anion at the selenium atom of the seleniranium cation accompanied by ring opening with the formation of (Z)-2-[(1,3-benzothiazol-2-ylsulfanyl)selanyl]ethenyl vinyl sulfide, which is converted to six-membered heterocycle, 2-(2,3-dihydro-1,4-thiaselenin-2-ylsulfanyl)-1,3-benzothiazole, in a 99% yield. The latter compound undergoes rearrangement with ring contraction producing five-membered heterocycle, 2-[(1,3-thiaselenol-2-ylmethyl)sulfanyl]-1,3-benzothiazole, in a 99% yield (the thermodynamic product). The formation of 1,2-bis[(Z)-2-(vinylsulfanyl)ethenyl] diselenide is the result of the disproportionation of (Z)-2-[(1,3-benzothiazol-2-ylsulfanyl)selanyl]ethenyl vinyl sulfide. Thus, based on the quantum chemical and experimental studies, a regioselective synthesis of the reaction products in high yields was developed.

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Synthesis, characterization and antibacterial activity of some new ferrocenyl selenazoles and 3,5-diferrocenyl-1,2,4-selenadiazole

Cited by 23 publications

References 28 publications

Synthetic Approaches to Organoselenium Derivatives with Antimicrobial and Anti-Biofilm Activity

Synthetic Approaches to Organoselenium Derivatives with Antimicrobial and Anti-Biofilm Activity

Novel 2-Hydroselenonicotinonitriles and Selenopheno[2, 3-b]pyridines: Efficient Synthesis, Molecular Docking-DFT Modeling, and Antimicrobial Assessment

Quantum Chemical and Experimental Studies of an Unprecedented Reaction Pathway of Nucleophilic Substitution of 2-Bromomethyl-1,3-thiaselenole with 1,3-Benzothiazole-2-thiol Proceeding Stepwise at Three Different Centers of Seleniranium Intermediates

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