Pt(ii)-activated coupling of aminoethylferrocene with benzonitrile. A facile access route to a new redox-active bis(ferrocenyl-amidine) anion sensor

Nieto, Daniel; González-Vadillo, Ana Ma; Bruña, Sonia; Pastor, César J.; Kaifer, Ángel E.; Cuadrado, Isabel

doi:10.1039/c1cc13704b

Cited by 23 publications

(22 citation statements)

References 34 publications

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“…The bond parameters around the Pt(II) atom in 8 are comparable with those parameters reported for the related trans -[PtCl 2 L 2 ] (L = ferrocenyl-based amidine and guanidine). 23,28…”

Section: Resultsmentioning

confidence: 99%

Critical Role of Anions in Platinum(II) Precursors upon the Structural Motifs of Six-Membered Cycloplatinated N,N′,N″-Triarylguanidines

Mishra

Thirupathi

2018

ACS Omega

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The reactions of cis -[Pt(OAc) 2 (DMSO) 2 ] with 2 equiv of sym N , N ′, N ″-triarylguanidines, [ArN=C(NHAr) 2 ], in toluene under reflux condition for 8 h afforded six-membered cycloplatinated guanidines, [Pt{κ 2 ( C , N )}(OAc){κ 1 N (ArN=C(NHAr) 2 )}] [ sym = symmetrical; Ar = 2-MeC 6 H 4 ( 1 ) and 2,4-Me 2 C 6 H 3 ( 2 )], in 82 and 84% yields, respectively. The salt metathesis reaction of 1 with 1 equiv of AgTFA in CH 2 Cl 2 at room temperature (RT) afforded [Pt{κ 2 ( C , N )}(TFA){κ 1 N (ArN=C(NHAr) 2 )}] ( 3 ) in 94% yield. The reaction of cis -[Pt(TFA) 2 (DMSO) 2 ] with 1 equiv of [ArN=C(NHAr) 2 ] in toluene under reflux condition for 8 h afforded six-membered cycloplatinated guanidines, [Pt{κ 2 ( C , N )}(TFA)(DMSO)] [Ar = 2-MeC 6 H 4 ( 4 ), 4-MeC 6 H 4 ( 5 ), 2,4-Me 2 C 6 H 3 ( 6 ), and 2-(MeO)C 6 H 4 ( 7 )], in ≥73% yields. The reaction of trans -[PtCl 2 (PhCN) 2 ] with 2 equiv of [ArN=C(NHAr) 2 ] in toluene under reflux condition for 48 h afforded trans -[PtCl 2 {ArN=C(NHAr) 2 } 2 ] [Ar = 2-MeC 6 H 4 ( 8 ) and 2,4-Me 2 C 6 H 3 ( 9 )] in 90 and 45% yields, respectively. Complexes 8 and 9 were separately refluxed in MeOH for 8 h to afford six-membered cycloplatinated guanidines, [Pt{κ 2 ( C , N )}(μ-Cl)] 2 ( 10 and 11 ), in 93 and 96% yields, respectively, with concomitant formation of the respective guanidinium salts, [(ArNH) 3 ...

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“…The bond parameters around the Pt(II) atom in 8 are comparable with those parameters reported for the related trans -[PtCl 2 L 2 ] (L = ferrocenyl-based amidine and guanidine). 23,28…”

Section: Resultsmentioning

confidence: 99%

Critical Role of Anions in Platinum(II) Precursors upon the Structural Motifs of Six-Membered Cycloplatinated N,N′,N″-Triarylguanidines

Mishra

Thirupathi

2018

ACS Omega

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“…Extensive applications of ferrocene and its derivative compounds in material science, homogeneous catalysis [15], nonlinear optics [16], and molecular sensors are observed [17]. Furthermore, an unexpected biological activity is often witnessed upon incorporating a fragment of ferrocene into a molecule of an organic compound [18].…”

Section: Ferrocene Derivativesmentioning

confidence: 99%

Supramolecular Chemistry and DNA Interaction Studies of Ferrocenyl Ureas and Thioureas

Kausar¹,

Altaf²,

Hamayun³

et al. 2021

Photophysics, Photochemical and Substitution Reactions - Recent Advances

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In this chapter, we have discussed the characteristics and bioapplicabilities of different ferrocene derivatives, for example, amides, amines, sulfonamide, and polymers, focusing mainly on urea and thiourea derivatives due to their autonomous and widespread spectroscopic action and bioactivities. Supramolecular chemistry of ferrocenyl ureas and thioureas is described owing to exploring their mode of interactions within and among the molecules and the role of these supramolecular structures in enhancing the DNA intercalation. DNA interaction studies of these ferrocenyl-based ureas and thioureas are explored with approaches like electrochemical study, viscosity measurements, molecular docking, electronic spectroscopy, dynamic light scattering (DLS), and radical scavenging activity. Attachment of ferrocene moiety to ureas an thiouereas closer to DNA is very promising strategy which most possibly boosts the probability of DNA damage and cell apoptosis which is responsible for enormous biological activities.

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“…Ferrocene and its derivatives find extensive applications in areas like homogeneous catalysis, material science, nonlinear optics, and molecular sensors [4][5][6][7][8][9][10]. Additionally, incorporation of a ferrocene fragment into a molecule of an organic compound often produces unexpected biological activity.…”

Section: Introductionmentioning

confidence: 99%

Ferrocene Derivatives Carrying Urea, Thiourea, and Sulfonamide Moieties: Synthesis and Evaluation of Antibacterial and Antifungal Activities

Yavuz

Yıldırım

2013

Journal of Chemistry

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In the present study, some novel ferrocene derivatives carrying urea, thiourea, and sulfonamide groups were synthesized, and all compounds were characterized by spectral and elemental analyses. These compounds were screened for their antibacterial activities and also their minimum inhibitory concentration (MIC) against Gram-positive bacteria (Staphylococcus aureusandBacillus subtilis) and Gram-negative bacteria (Klebsiella pneumoniaandEscherichia coli) and antifungal activities againstSaccharomyces cerevisiaeandCandida albicans. Amongst the tested compounds,4b,4c,5b, and6bdisplayed excellent antimicrobial activity.

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Pt(ii)-activated coupling of aminoethylferrocene with benzonitrile. A facile access route to a new redox-active bis(ferrocenyl-amidine) anion sensor

Cited by 23 publications

References 34 publications

Critical Role of Anions in Platinum(II) Precursors upon the Structural Motifs of Six-Membered Cycloplatinated N,N′,N″-Triarylguanidines

Critical Role of Anions in Platinum(II) Precursors upon the Structural Motifs of Six-Membered Cycloplatinated N,N′,N″-Triarylguanidines

Supramolecular Chemistry and DNA Interaction Studies of Ferrocenyl Ureas and Thioureas

Ferrocene Derivatives Carrying Urea, Thiourea, and Sulfonamide Moieties: Synthesis and Evaluation of Antibacterial and Antifungal Activities

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