Antibacterial 3-(arylamino)-1-ferrocenylpropan-1-ones: Synthesis, spectral, electrochemical and structural characterization

Damljanović, Ivan; Stevanović, Dragana; Pejović, Anka; Vukićević, Mirjana; Novaković, Sladjana B.; Bogdanović, Goran A.; Mihajlov-Krstev, Tatjana; Radulović, Niko S.; Vukićević, Rastko D.

doi:10.1016/j.jorganchem.2011.08.016

Cited by 38 publications

(27 citation statements)

References 65 publications

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“…3-(Arylamino)-1-ferrocenyl-1-propanones 111 ( Fig. 21) showed broad spectrum activity against both Gram-positive and Gram-negative bacteria, the highest degree of growth inhibition being obtained for S. aureus [139]. MIC values varied between 0.2 and 12.5 mg/mL, making these compounds approximately 100-fold less active than reference drug tetracycline.…”

Section: Antibacterial Activitymentioning

confidence: 99%

Mannich bases in medicinal chemistry and drug design

Roman¹

2015

European Journal of Medicinal Chemistry

281

110

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The biological activity of Mannich bases, a structurally heterogeneous class of chemical compounds that are generated from various substrates through the introduction of an aminomethyl function by means of the Mannich reaction, is surveyed, with emphasis on the relationship between structure and biological activity. The review covers extensively the literature reports that have disclosed Mannich bases as anticancer and cytotoxic agents, or compounds with potential antibacterial and antifungal activity in the last decade. The most relevant studies on the activity of Mannich bases as antimycobacterial agents, antimalarials, or antiviral candidates have been included as well. The review contains also a thorough coverage of anticonvulsant, anti-inflammatory, analgesic and antioxidant activities of Mannich bases. In addition, several minor biological activities of Mannich bases, such as their ability to regulate blood pressure or inhibit platelet aggregation, their antiparasitic and anti-ulcer effects, as well as their use as agents for the treatment of mental disorders have been presented. The review gives in the end a brief overview of the potential of Mannich bases as inhibitors of various enzymes or ligands for several receptors.

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Section: Antibacterial Activitymentioning

confidence: 99%

Mannich bases in medicinal chemistry and drug design

Roman¹

2015

European Journal of Medicinal Chemistry

281

110

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“…First, alkylation of amines ( 1‐3, 5 and 10–17 ) by β‐haloalkyl ketones and arylamines as reported by Martin Escolano et al. was undertaken; second, the Michael addition reaction between vinyl ketones and arylamines ( 4, 6–9 and 24–26 ) described in the literature; third, the Mannich reaction of methyl ketones with the respective arylamine and 1,3‐dioxolane was executed ( 18‐23 ) based on our previous experience and published literature . In this paper, the synthesis routes are shown in Schemes and .…”

Section: Discussion and Resultsmentioning

confidence: 99%

Antichagasic profile of a Series of Mannich Base‐Type Derivatives: Design, Synthesis, in vitro Evaluation, and Computational Studies Involving Iron Superoxide Dismutase

et al. 2019

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Chagas disease is a silent disease that continues to endanger millions of people and, due to its insufficient current chemotherapy, urgently requires the development of more effective drugs. With this objective, twenty‐six Mannich base derivatives were synthesized, and their in vitro activity was evaluated against Trypanosoma cruzi. Three out of the twenty‐six compounds showed interesting results, including IC50 values<10 μM and a selectivity index >20 in amastigote forms of Arequipa and SN3 T. cruzi strains. In addition, these compounds showed similar infection rates in Vero cells compared to those of benznidazole at 50 μM. Finally, some studies were performed to investigate the possible mechanism of action; moreover, computational studies proposed a binding mode of these derivatives to Fe‐SOD. This new series of compounds has an encouraging antichagasic profile with a simplified structure and synthetic routes. Therefore, the most active compounds should be considered as leads for further optimization of the antichagasic activity.

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“…For related structures and details of the synthesis, see: Damljanović et al (2011); Pejović et al (2012); Stevanović et al (2012); Leka et al (2012a,b,c).…”

Section: Related Literaturementioning

confidence: 99%

“…In the course of our studies of different ferrocene derivatives containing two or more heteroatoms, we have synthesized and determined the crystal structures of a series of 3-(arylamino)-1-ferrocenylpropan-1-ones (Damljanović et al 2011Leka et al 2012a. The present derivative 1-ferrocenyl-3-(3-acetylphenylamino)propan-1-one, crystallizes with two independent molecules (A and B) in the asymmetric unit (Fig.…”

Section: Commentmentioning

confidence: 99%

3-(3-Acetylanilino)-1-ferrocenylpropan-1-one

et al. 2012

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The title ferrocene-containing Mannich base, [Fe(C5H5)(C16H16NO2)], crystallizes with two independent molecules (A and B) in the asymmetric unit. Molecules A and B have similar conformations. The dihedral angles between the best planes of the benzene and substituted cyclopentadienyl rings are 88.59 (9) and 84.39 (10)° in A and B, respectively. In the crystal, the independent molecules form centrosymmetric dimers via corresponding N—H⋯O hydrogen bonds. The dimers further arrange via C—H⋯π and C—H⋯O interactions. There are no significant interactions between the A and B molecules.

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Antibacterial 3-(arylamino)-1-ferrocenylpropan-1-ones: Synthesis, spectral, electrochemical and structural characterization

Cited by 38 publications

References 65 publications

Mannich bases in medicinal chemistry and drug design

Mannich bases in medicinal chemistry and drug design

Antichagasic profile of a Series of Mannich Base‐Type Derivatives: Design, Synthesis, in vitro Evaluation, and Computational Studies Involving Iron Superoxide Dismutase

3-(3-Acetylanilino)-1-ferrocenylpropan-1-one

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