Synthesis and biological evaluation of novel ferrocene–naphthoquinones as antiplasmodial agents

García-Barrantes, Pedro M.; Lamoureux, Guy; Pérez, Alice L.; García‐Sánchez, Rory N.; Martínez, Antonio; Feliciano, Arturo San

doi:10.1016/j.ejmech.2013.10.011

Cited by 54 publications

(25 citation statements)

References 63 publications

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“…Gram-positive bacterium possesses a thicker membrane with a diverse lipid profile that may increase ferrocene-membrane interactions [12]. Ferrocene compounds are lipophilic and allowing better penetration across the more lipophilic membrane present in the Gram-positive bacteria [13]. The organometallic redox active species Fc-Py did not showed any antibacterial activity against microorganisms tested, only ferrocene complexes with halogenated phenols demonstrated antibacterial properties [Table/Fig-4].…”

Section: Discussionmentioning

confidence: 99%

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Para-Substituted Functionalised Ferrocene Esters with Novel Antibacterial Properties

Forti

Bernard

Santiago-Collazo

et al. 2018

JCDR

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Introduction Bacterial antibiotic resistance is on rise despite advances in the development of new antibiotics. In an attempt to circumvent resistance, scientists are shifting focus from modifying existent antibiotics to identifying new antibiotic compounds. Aim To assess the potential antibiotic effects of functionalised ferrocenecarboxylates para-substituted on the phenoxy pendant group to form: 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl and 4-(H-pyrrol-1-yl)phenyl. Materials and Methods For this, we employed the Kirby-Bauer disc diffusion method using a collection of nine bacterial species: Staphylococcus aureus, Escherichia coli, Micrococcus luteus, Pseudomonas aeruginosa, Serratia marcescens, Klebsiella pneumoniae, Bacillus subtilis, Proteus vulgaris and Enterobacter aerogenes. Results The results show that all four-halogen substituted ferrocenecarboxylates 4-fluorophenyl (23.33 μM, 11.66 μM, 5.83 μM), 4-chlorophenyl (10.16 μM, 5.08 μM, 2.54 μM), 4-bromophenyl (9.0 μM, 4.5 μM, 2.25 μM), and 4-iodophenyl (17.12 μM, 8.56 μM, 4.28 μM) exhibited an antibacterial effect by reducing proliferation of Bacillus subtilis. Meanwhile, only 4-bromophenyl (9.0 μM) and 4-chlorophenyl (10.16 μM) ferrocenecarboxylates were able to decrease the growth of Micrococcus luteus. Conclusion Hence, functionalised ferrocenecarboxylates para-substituted with small and simple groups represent a novel class of bio-organometallic compounds with the potential to be used as antibacterial agents.

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Section: Discussionmentioning

confidence: 99%

“…Previous studies, have demonstrated antibacterial, antimalarial, and antifungal properties of ferrocenes derivatised with large complex groups or substituted with known antimicrobials [4, 13–15, 17]. On the contrary, these compounds do not contain such substitutions, which may be susceptible to degradation and inhibition by microorganisms.…”

Section: Discussionmentioning

confidence: 99%

Para-Substituted Functionalised Ferrocene Esters with Novel Antibacterial Properties

Forti

Bernard

Santiago-Collazo

et al. 2018

JCDR

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“…Recently, García‐Barrantes et al demonstrated the synthesis of ferrocenenaphthoquinones by integration of 1,4‐naphthoquinone and ferrocenemethanol derivatives. The process was carried out ‘in water’ at moderate temperature without using any catalyst and auxiliaries.…”

Section: Applicationsmentioning

confidence: 99%

Recent advances in the synthesis, biological activities and various applications of ferrocene derivatives

Larik

Saeed

Fattah

et al. 2016

Applied Organom Chemis

117

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Ferrocene derivatives constitute an important class of organometallic compounds with not only an extensive range of biological activities but also diverse industrial as well as material science applications. These stimulating features of ferrocene derivatives spurred us to review the recent advances in synthesis methods and biological and other applications reported in the latest literature. An effort has been made to summarize the recent developments in synthetic methods providing access to ferrocene scaffolds and the useful medicinal and material applications, including agricultural, catalytic, polymer, conducting, redox mediating, ferrocenyl stationary phase, rocket propellant and ion sensing applications. Ferrocene‐based bulky metallocenes are also discussed.

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“…1,3,4 Among a variety of ferrocene derivatives, functionalized molecules bearing the methylferrocene moiety are of special interest owing to their useful properties. These compounds have been shown to serve as potential drugs (anticancer, 8 antitumor, 9 antimalarial, 10 antiplasmodial, 11 antimycobacterial, 12 antimicrobial, 13 anticandidal 14 and antiproliferative 15 agents), efficient ligands for catalysis, 3,4 monomers for functional polymers, 16 ionic liquids 17 and molecular sensors. 18 Today, one of the most efficient and straightforward approaches to access methylferrocene derivatives is the reaction of various nucleophiles with ferrocenylmethylating reagents, 19 among which [FcCH 2 NMe 3 ]I, FcCH 2 NMe 2 and FcCH 2 OH are the most available.…”

Section: Introductionmentioning

confidence: 99%

Unexpected acid-catalyzed ferrocenylmethylation of diverse nucleophiles with vinyloxymethylferrocene

et al. 2016

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Synthesis and biological evaluation of novel ferrocene–naphthoquinones as antiplasmodial agents

Cited by 54 publications

References 63 publications

Para-Substituted Functionalised Ferrocene Esters with Novel Antibacterial Properties

Para-Substituted Functionalised Ferrocene Esters with Novel Antibacterial Properties

Recent advances in the synthesis, biological activities and various applications of ferrocene derivatives

Unexpected acid-catalyzed ferrocenylmethylation of diverse nucleophiles with vinyloxymethylferrocene

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