Antimicrobial and Antitumor Activity of Enantiopure Pybox–Osmium Complexes

Menéndez-Pedregal, Estefanía; Manteca, Ángel; Sánchez, Jesús; Dı́ez, Josefina; Gamasa, M. Pilar; Lastra, Elena

doi:10.1002/ejic.201403173

Cited by 9 publications

(5 citation statements)

References 44 publications

(24 reference statements)

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“…Pincer compounds are having tremendous impact in the modern chemistry of transition metal, in particular those of platinum group . The mer -disposition of the donor atoms of the ligands allows to design complexes with applications ranging from catalysis and medicine to material science . Furthermore, because complexes with these ligands are generally very robust, they have been used as intermediates in synthetic procedures requiring drastic experimental conditions.…”

Section: Introductionmentioning

confidence: 99%

2-Azetidinones as Precursors of Pincer Ligands: Preparation, Structure, and Spectroscopic Properties of CC′N-Osmium Complexes

Casarrubios¹,

Esteruelas

Larramona

et al. 2015

Inorg. Chem.

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A metal-promoted degradation of 2-azetidinones to afford CC'N-pincer ligands is reported. The hexahydride complex OsH6(P(i)Pr3)2 (1) reacts with (±)-cis-1-(4-methoxyphenyl)-3-phenoxy-4-(pyridin-2-yl)azetidin-2-one (I), (±)-cis-1-(4-methoxyphenyl)-3-phenoxy-4-(isoquinolin-2-yl)azetidin-2-one (II), and (±)-cis-1-(4-methoxyphenyl)-3-phenoxy-4-(quinolin-2-yl)azetidin-2-one (III) to give the respective OsH2(P(i)Pr3)2(CC'N) (2-4) complexes, which add HBF4·OEt2 to yield [OsH2(P(i)Pr3)2(CC″N)]BF4 (5-7). These salts are the result of the addition of the proton of the acid to the dianionic CC'N-pincer ligand. The hydride ligands of these compounds undergo quantum mechanical exchange coupling, which has been experimentally quantified according to a two-dimensional harmonic oscillator model, where Jex is determined by the separation between the hydrides, their hard sphere radius, and a ν parameter describing the H-M-H vibrational wag mode allowing the movement along the H-H vector. The comparison of the results reveals that the phenomenon is particularly intense for 5-7. Furthermore, in these compounds, the separation between the hydrides is ∼0.1 Å shorter than in the respective neutral species 2-4, whereas the hydride hard sphere radius increases by ∼10%, and the ν value decreases by ∼20%.

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Section: Introductionmentioning

confidence: 99%

2-Azetidinones as Precursors of Pincer Ligands: Preparation, Structure, and Spectroscopic Properties of CC′N-Osmium Complexes

Casarrubios¹,

Esteruelas

Larramona

et al. 2015

Inorg. Chem.

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“…Osmium ComplexesThere are only a few reports that have appeared lately detailing antimicrobial studies of osmium complexes. In 2015, a series of enantiopure (S,S)-iPr-pybox and {(S,S)-iPr-pybox = 2,6-bis[4(S)isopropyloxazolin-2-yl]pyridine} osmium(II) complexes (36,Figure 8), were prepared by Menéndez-Pedregal and coworkers[101]. The complexes were screened against M. luteus, B. subtilis, E. coli, S. coelicolor, S. antibioticus, and P. aeruginosa bacteria.…”

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confidence: 99%

Recent Studies on the Antimicrobial Activity of Transition Metal Complexes of Groups 6–12

Sovari

Zobi

2020

Chemistry

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Antimicrobial resistance is an increasingly serious threat to global public health that requires innovative solutions to counteract new resistance mechanisms emerging and spreading globally in infectious pathogens. Classic organic antibiotics are rapidly exhausting the structural variations available for an effective antimicrobial drug and new compounds emerging from the industrial pharmaceutical pipeline will likely have a short-term and limited impact before the pathogens can adapt. Inorganic and organometallic complexes offer the opportunity to discover and develop new active antimicrobial agents by exploiting their wide range of three-dimensional geometries and virtually infinite design possibilities that can affect their substitution kinetics, charge, lipophilicity, biological targets and modes of action. This review describes recent studies on the antimicrobial activity of transition metal complexes of groups 6–12. It focuses on the effectiveness of the metal complexes in relation to the rich structural chemical variations of the same. The aim is to provide a short vade mecum for the readers interested in the subject that can complement other reviews.

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“…Transition-metal complexes stabilized by pincer ligands are having a great effect on modern chemistry because of their high stability and the broad range of their applications, which extend from catalysis and medicine to materials science . Thus, platinum-group metal pincer complexes are currently situated at the forefront of important fields such as homogeneous catalysis and photophysics .…”

Section: Introductionmentioning

confidence: 99%

Assembly of a Dihydrideborate and Two Aryl Nitriles to Form a C,N,N′-Pincer Ligand Coordinated to Osmium

et al. 2021

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The C,N,N'-donor aryl-diimineborate pincer ligand of complexes OsH2{κ 3 -C,N,N-[C6H3RCH=NB(cat)N=CHC6H4R]}(P i Pr3)2 (R = H, Me) has been generated in a one-pot procedure, by the reaction of the hexahydride OsH6(P i Pr3)2 with catecholborane (catBH) and two molecules of the corresponding aryl nitrile. The osmium-pincer bonding situation has been analyzed by means of Atoms In Molecules (AIM), Natural Bond Orbital (NBO), and Energy Decomposition Analysis coupled with the Natural Orbitals for Chemical Valence (EDA−NOCV) methods. According to the results, it exhibits a rather strong electron-sharing Os-C bond, two weaker donor-acceptor N-to-Os bonds, and two π-backdonations from the transition metal to vacant π* orbitals of the formed metallacycles. In addition, spectroscopic findings and DFT calculations reveal that the donor units of the pincer are incorporated in a sequential manner. Firstly, the central Os-N bond is formed, by the reaction of the dihydrideborate ligand of intermediate OsH3{κ 2 -H,H-(H2Bcat)}(P i Pr3)2 with one of the aryl nitriles. The subsequent oxidative addition of the ortho-C-H bond of the aryl substituent of the resulting κ 1 -N-(N-boryl-arylaldimine) affords the Os-C bond. Lastly, the second Os-N bond is generated from a hydride, an orthometalated Nboryl-arylaldimine and the second aryl nitrile.

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Antimicrobial and Antitumor Activity of Enantiopure Pybox–Osmium Complexes

Cited by 9 publications

References 44 publications

2-Azetidinones as Precursors of Pincer Ligands: Preparation, Structure, and Spectroscopic Properties of CC′N-Osmium Complexes

2-Azetidinones as Precursors of Pincer Ligands: Preparation, Structure, and Spectroscopic Properties of CC′N-Osmium Complexes

Recent Studies on the Antimicrobial Activity of Transition Metal Complexes of Groups 6–12

Assembly of a Dihydrideborate and Two Aryl Nitriles to Form a C,N,N′-Pincer Ligand Coordinated to Osmium

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