Reactivity study of arene(azido)ruthenium N∩O-base complexes with activated alkynes

Nongbri, Saphidabha L.; Therrien, Bruno; Rao, Kollipara Mohan

doi:10.1016/j.ica.2011.07.004

Cited by 26 publications

(13 citation statements)

References 46 publications

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“…We and others have developed ruthenium compounds of 8-oxyquinolinederived ligands. 31,[43][44][45][46][47] Organoruthenium compounds of 8-oxyquinoline derived from clioquinol have shown promising antiproliferative activities, but they have poor aqueous solubility.…”

Section: Introductionmentioning

confidence: 99%

Making organoruthenium complexes of 8-hydroxyquinolines more hydrophilic: impact of a novel l-phenylalanine-derived arene ligand on the biological activity

et al. 2018

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Ru(arene) compounds have many desirable features making them promising candidates for further development in anticancer drug research. While a lot of emphasis has been placed on the modification of the ancillary ligands, there are not many examples of arene ligands bearing functional groups. Herein, we report the preparation of [Ru(arene)(8-oxyquinolinato)Cl] complexes with the arene being a protected form of the amino acid l-phenylalanine and 8-oxyquinolinato ligand substituted with halogens. With this approach we aimed to alter the pharmacological properties of the complexes and address issues with the aqueous solubility of the analogous p-cymene complexes. The complexes were shown to be stable in DMSO and water and reacted readily with l-histidine and 9-ethylguanine as protein and DNA models, respectively. Assaying the antiproliferative activity in cancer cells gave IC values in the low μM range. While the lipophilicity of the p-cymene analogues correlated well with their in vitro cytotoxicity, the potency of the complexes with the l-phenylalanine-derived arene was independent of lipophilicity.

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Section: Introductionmentioning

confidence: 99%

Making organoruthenium complexes of 8-hydroxyquinolines more hydrophilic: impact of a novel l-phenylalanine-derived arene ligand on the biological activity

et al. 2018

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“…These two species could arise due to either linkage isomerism caused by the triazolate ligand ( N 1 vs. N 2 coordination) or the p ‐cymene ring rotation about the metal as discussed previously for 8 . If the observed 1 H NMR spectral pattern is due to linkage isomerism, one would then anticipate three quartets for C H 2 CH 3 protons with two of these quartets being of equal intensity and three triplets for CH 2 C H 3 protons with two of these triplets being of equal intensity . The 1 H NMR spectrum of 9 revealed the presence of two triplets for CH 3 protons and two quartets for CH 2 protons of the C(O)OEt moiety both in about 1.00:0.05 ratio which suggest the cause of two isomers being the p ‐cymene ring rotation about the metal centre …”

Section: Resultsmentioning

confidence: 98%

“…Further, SbF 6 – is present outside the coordination sphere of the metal in 8· MeOH. The triazolate ligand in 9 is coordinated to the Ru(II) atom through the central N atom ( N2 coordination mode) and this coordination mode is believed to be the result of the formation of a thermodynamic product , . The structurally characterized N1 coordinated triazolate complexes are uncommon with a few exceptions while N2 coordinated triazolate complexes are common.…”

Section: Resultsmentioning

confidence: 99%

Half Sandwich Electron Deficient N,N′,N′′‐Triarylguanidinatoruthenium(II) Complexes: Syntheses, Reactivity Studies, and Structural Aspects

Kumar

Ujjval

2019

Eur J Inorg Chem

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Three symmetrical N,N′,N′′-triarylguanidinatoruthenium(II) complexes, [(η 6 -p-cymene)RuCl{κ 2 (N,N′)((ArN) 2 C-N(H)Ar)}] (Ar = 2-(CF 3 )C 6 H 4 (1), 4-(CF 3 )C 6 H 4 (2) and 3,5-(CF 3 ) 2 C 6 H 3 (3)) were isolated in good yields. The reaction of 3 with NaOAc, NaN 3 and KSCN afforded [(η 6 -p-cymene)RuX{κ 2 (N,N′)((ArN) 2 C-N(H)Ar)}] (X = OAc (4), N 3 (5) and an admixture of SCN (6) and NCS (7)) respectively in very good yields. On the other hand, metathesis reaction of 3 with AgSbF 6 in the presence of MeCN afforded [(η 6 -pcymene)Ru(MeCN){κ 2 (N,N′)((ArN) 2 C-N(H)Ar)}][SbF 6 ] (8) in good yield. Complex 5 upon treatment with diethylacetylenedicarboxylate and bis(diphenylphosphanyl)acetylene separately afforded [a]

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“…This finding was attributed to electronic factors, i.e., the higher +I-effect of the ethoxy group in comparison with the methoxy group. [68,434] Besides dialkylacetylene dicarboxylate, the activated alkyne F 3 C-CϵC-CF 3 , [185] in situ prepared benzyne (from anthranilic acid and nitrite), [183a] and H-CϵC-CN (generated from Z-or E-NC(H)C=C(H)CN)) have been used as dipolarophiles. [68-70,178,179,285a,432,433] The formation of 4-cyano-1,2,3-triazole from the dinitriles of fumaric or maleic acid and organic azides with elimination of HCN was first observed by Huisgen and Szeimies.…”

Section: Reviewmentioning

confidence: 99%

Azide Chemistry – An Inorganic Perspective, Part II^[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

Fehlhammer

Beck

2015

Zeitschrift anorg allge chemie

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Abstract. In whatever state of bonding -whether covalent to an organic residue or a heteroatom, or polar to ionic in contact with a metal -the azide moiety N 3 is characterized by its high potential of reactivity which essentially manifests itself in two basic processes: the elimination of dinitrogen and the entry into 1,3-dipolar cycloadditions with suitable dipolarophiles, the latter of which clearly predominates the chemistry of azide, also that of its metal compounds. In a preceding review entitled "Part I -Metal Azides: Overview, General Trends and Recent Developments" which was meant to lay the foundations for the present paper, these and other reactions have already been touched upon. The present review -Part II -now focusses in great detail on the formation of five-membered heterocyclestetrazol(at)es, triazol(at)es, triazolin(at)es, thiatriazol(at)es, etc. as well as various consecutive products -from azide and nitriles, isocyanides, alkynes, alkenes and heteroallenes (CS 2 , RN=C=S) in the ligand sphere of the metal. Generally, these [3+2]-cycloadditions are found to CONTENTS

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Reactivity study of arene(azido)ruthenium N∩O-base complexes with activated alkynes

Cited by 26 publications

References 46 publications

Making organoruthenium complexes of 8-hydroxyquinolines more hydrophilic: impact of a novel l-phenylalanine-derived arene ligand on the biological activity

Making organoruthenium complexes of 8-hydroxyquinolines more hydrophilic: impact of a novel l-phenylalanine-derived arene ligand on the biological activity

Half Sandwich Electron Deficient N,N′,N′′‐Triarylguanidinatoruthenium(II) Complexes: Syntheses, Reactivity Studies, and Structural Aspects

Azide Chemistry – An Inorganic Perspective, Part II^[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

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Reactivity study of arene(azido)ruthenium N∩O-base complexes with activated alkynes

Cited by 26 publications

References 46 publications

Making organoruthenium complexes of 8-hydroxyquinolines more hydrophilic: impact of a novel l-phenylalanine-derived arene ligand on the biological activity

Making organoruthenium complexes of 8-hydroxyquinolines more hydrophilic: impact of a novel l-phenylalanine-derived arene ligand on the biological activity

Half Sandwich Electron Deficient N,N′,N′′‐Triarylguanidinatoruthenium(II) Complexes: Syntheses, Reactivity Studies, and Structural Aspects

Azide Chemistry – An Inorganic Perspective, Part II[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems

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Azide Chemistry – An Inorganic Perspective, Part II^[‡][3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems