2013
|
Synthesis, characterization, and antiproliferative activities of novel ferrocenophanic suberamides against human triple-negative MDA-MB-231 and hormone-dependent MCF-7 breast cancer cells Article de journal J D J Cázares-Marinero; O Buriez; E Labbé; S Top; C Amatore; G Jaouen Organometallics, 32 (20), p. 5926–5934, 2013. @article{Cazares-Marinero:2013,
title = {Synthesis, characterization, and antiproliferative activities of novel ferrocenophanic suberamides against human triple-negative MDA-MB-231 and hormone-dependent MCF-7 breast cancer cells},
author = {J D J C\'{a}zares-Marinero and O Buriez and E Labb\'{e} and S Top and C Amatore and G Jaouen},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84887042245&doi=10.1021%2fom400490a&partnerID=40&md5=efad7ad74b52eb66a59d23ca2a8a9b3e},
doi = {10.1021/om400490a},
year = {2013},
date = {2013-01-01},
journal = {Organometallics},
volume = {32},
number = {20},
pages = {5926--5934},
abstract = {We report the synthesis and characterization of a new family of organometallic suberamides with strong antiproliferative activities against triple-negative MDA-MB-231 breast cancer cell lines with IC50 values ranging from 0.84 to 0.94 μM. Similar studies on hormone-dependent MCF-7 breast cancer cells were also carried out, revealing the positive effect of the ferrocenophanic moiety on disubstituted ferrocene-1,1′-diyl derivatives versus their monosubstituted ferrocenyl analogues. Cyclic voltammetry analysis showed no substantial differences between ferrocenic and ferrocenophanic suberamides in the absence or presence of a base. However, similar studies performed on related compounds strongly suggest that ferrocenophanic and ferrocenic complexes do not undergo the same redox activation patterns. The electrochemical behavior seems to be in agreement with the antiproliferative activity of this type of organometallic compound. © 2013 American Chemical Society.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
We report the synthesis and characterization of a new family of organometallic suberamides with strong antiproliferative activities against triple-negative MDA-MB-231 breast cancer cell lines with IC50 values ranging from 0.84 to 0.94 μM. Similar studies on hormone-dependent MCF-7 breast cancer cells were also carried out, revealing the positive effect of the ferrocenophanic moiety on disubstituted ferrocene-1,1′-diyl derivatives versus their monosubstituted ferrocenyl analogues. Cyclic voltammetry analysis showed no substantial differences between ferrocenic and ferrocenophanic suberamides in the absence or presence of a base. However, similar studies performed on related compounds strongly suggest that ferrocenophanic and ferrocenic complexes do not undergo the same redox activation patterns. The electrochemical behavior seems to be in agreement with the antiproliferative activity of this type of organometallic compound. © 2013 American Chemical Society. |
The effect of protic electron donor aromatic substituents on ferrocenic and [3]ferrocenophanic anilines and anilides: Some aspects of structureeactivity relationship studies on organometallic compounds with strong antiproliferative effects Article de journal J De Jesús Cázares-Marinero; E Labbé; S Top; O Buriez; C Amatore; G Jaouen Journal of Organometallic Chemistry, 744 , p. 92–100, 2013. @article{DeJesusCazares-Marinero:2013,
title = {The effect of protic electron donor aromatic substituents on ferrocenic and [3]ferrocenophanic anilines and anilides: Some aspects of structureeactivity relationship studies on organometallic compounds with strong antiproliferative effects},
author = {J De Jes\'{u}s C\'{a}zares-Marinero and E Labb\'{e} and S Top and O Buriez and C Amatore and G Jaouen},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84884534415&doi=10.1016%2fj.jorganchem.2013.05.047&partnerID=40&md5=8eb52ab8222684eaee90937ebd7e591c},
doi = {10.1016/j.jorganchem.2013.05.047},
year = {2013},
date = {2013-01-01},
journal = {Journal of Organometallic Chemistry},
volume = {744},
pages = {92--100},
abstract = {A new family of nitrogenous derivatives is synthesized, characterized and evaluated for the investigation of the impact of some structural motifs such as functionalization and conjugation on the antiproliferative activity of ferrocenic complexes against cancer cells. These compounds are 4,40-([3]ferrocenophan-1-ylidenemethylene)dianilides and tetramethylated dianilines derived from Michler's ketone. An alternative McMurry direct heterocoupling method for 4,40-([3]ferrocenophan-1-ylidenemethylene)dianiline synthesis is described and electrochemical studies are also discussed. © 2013 Elsevier B.V. All rights reserved.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
A new family of nitrogenous derivatives is synthesized, characterized and evaluated for the investigation of the impact of some structural motifs such as functionalization and conjugation on the antiproliferative activity of ferrocenic complexes against cancer cells. These compounds are 4,40-([3]ferrocenophan-1-ylidenemethylene)dianilides and tetramethylated dianilines derived from Michler's ketone. An alternative McMurry direct heterocoupling method for 4,40-([3]ferrocenophan-1-ylidenemethylene)dianiline synthesis is described and electrochemical studies are also discussed. © 2013 Elsevier B.V. All rights reserved. |
2012
|
Deciphering the activation sequence of ferrociphenol anticancer drug candidates Article de journal P Messina; E Labbé; O Buriez; E A Hillard; A Vessières; D Hamels; S Top; G Jaouen; Y M Frapart; D Mansuy; C Amatore Chemistry - A European Journal, 18 (21), p. 6581–6587, 2012. @article{Messina:2012,
title = {Deciphering the activation sequence of ferrociphenol anticancer drug candidates},
author = {P Messina and E Labb\'{e} and O Buriez and E A Hillard and A Vessi\`{e}res and D Hamels and S Top and G Jaouen and Y M Frapart and D Mansuy and C Amatore},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84861159405&doi=10.1002%2fchem.201103378&partnerID=40&md5=bf764a18b4bd832d2149e1a5cbc90875},
doi = {10.1002/chem.201103378},
year = {2012},
date = {2012-01-01},
journal = {Chemistry - A European Journal},
volume = {18},
number = {21},
pages = {6581--6587},
abstract = {The complete oxidation sequence of a model for ferrociphenols, a new class of anticancer drug candidate, is reported. Cyclic voltammetry was used to monitor the formation of oxidation intermediates on different timescales, thereby allowing the electrochemical characterization of both the short-lived and stable species obtained from the successive electron-transfer and deprotonation steps. The electrochemical preparation of the ferrocenium intermediate enabled a stepwise voltammetric determination of the stable oxidation compounds obtained upon addition of a base as well as the electron stoichiometry observed for the overall oxidation process. A mechanism has been established from the electrochemical data, which involves a base-promoted intramolecular electron transfer between the phenol and the ferrocenium cation. The resulting species is further oxidized then deprotonated to yield a stable quinone methide. To further characterize the transient species successively formed during the two-electron oxidation of the ferrociphenol to its quinone methide, EPR was used to monitor the fate of the paramagnetic species generated upon addition of imidazole to the electrogenerated ferrocenium. The study revealed the passage from an iron-centered to a carbon-centered radical, which is then oxidized to yield the quinone methide, namely, the species that interacts with proteins and so forth under biological conditions. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
The complete oxidation sequence of a model for ferrociphenols, a new class of anticancer drug candidate, is reported. Cyclic voltammetry was used to monitor the formation of oxidation intermediates on different timescales, thereby allowing the electrochemical characterization of both the short-lived and stable species obtained from the successive electron-transfer and deprotonation steps. The electrochemical preparation of the ferrocenium intermediate enabled a stepwise voltammetric determination of the stable oxidation compounds obtained upon addition of a base as well as the electron stoichiometry observed for the overall oxidation process. A mechanism has been established from the electrochemical data, which involves a base-promoted intramolecular electron transfer between the phenol and the ferrocenium cation. The resulting species is further oxidized then deprotonated to yield a stable quinone methide. To further characterize the transient species successively formed during the two-electron oxidation of the ferrociphenol to its quinone methide, EPR was used to monitor the fate of the paramagnetic species generated upon addition of imidazole to the electrogenerated ferrocenium. The study revealed the passage from an iron-centered to a carbon-centered radical, which is then oxidized to yield the quinone methide, namely, the species that interacts with proteins and so forth under biological conditions. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
Direct electrochemical reduction of organic halide droplets dispersed in water Article de journal E Deunf; E Labbé; J N Verpeaux; O Buriez; C Amatore RSC Advances, 2 (12), p. 5398–5402, 2012. @article{Deunf:2012,
title = {Direct electrochemical reduction of organic halide droplets dispersed in water},
author = {E Deunf and E Labb\'{e} and J N Verpeaux and O Buriez and C Amatore},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84893242167&doi=10.1039%2fc2ra20215h&partnerID=40&md5=0fb6823ae35567936f7b5119862facae},
doi = {10.1039/c2ra20215h},
year = {2012},
date = {2012-01-01},
journal = {RSC Advances},
volume = {2},
number = {12},
pages = {5398--5402},
abstract = {The direct electroreductive homocoupling of benzyl bromide has been efficiently achieved using water as the solvent. This process does not involve any organic co-solvent, transition metal catalyst, oil, surfactants, but only a cheap and non-toxic supporting electrolyte (KCl). Benzyl bromide droplets dispersed in water were reduced at a low current density, in an undivided cell fitted with a sacrificial aluminum anode. Various cathode materials have been tested (Ni, Pt, C, Ag) to favor organic halide reduction versus hydrogen evolution. Moreover, it was shown that the presence of aluminum cations generated by the oxidation of the anode played a crucial role in the efficiency of the electrochemical reduction step. Surprisingly, this property was exalted in acidic solutions (pH = 1). Under such acidic conditions, both bibenzyl proportion and faradaic yields were considerably improved. The electrochemical activation of energetically stronger C-X bonds such as those encountered in benzyl chloride (Csp3-Cl) or ethyl 4-iodobenzoate (Csp2-I) could be also achieved in water though resulted in lower faradaic yields. From a mechanistic point of view, both the faradaic yields and the product distribution obtained under various conditions suggested the occurrence of a radical coupling pathway occurring within the organic droplets or at their surface. © 2012 The Royal Society of Chemistry.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
The direct electroreductive homocoupling of benzyl bromide has been efficiently achieved using water as the solvent. This process does not involve any organic co-solvent, transition metal catalyst, oil, surfactants, but only a cheap and non-toxic supporting electrolyte (KCl). Benzyl bromide droplets dispersed in water were reduced at a low current density, in an undivided cell fitted with a sacrificial aluminum anode. Various cathode materials have been tested (Ni, Pt, C, Ag) to favor organic halide reduction versus hydrogen evolution. Moreover, it was shown that the presence of aluminum cations generated by the oxidation of the anode played a crucial role in the efficiency of the electrochemical reduction step. Surprisingly, this property was exalted in acidic solutions (pH = 1). Under such acidic conditions, both bibenzyl proportion and faradaic yields were considerably improved. The electrochemical activation of energetically stronger C-X bonds such as those encountered in benzyl chloride (Csp3-Cl) or ethyl 4-iodobenzoate (Csp2-I) could be also achieved in water though resulted in lower faradaic yields. From a mechanistic point of view, both the faradaic yields and the product distribution obtained under various conditions suggested the occurrence of a radical coupling pathway occurring within the organic droplets or at their surface. © 2012 The Royal Society of Chemistry. |
Electrochemical studies of cell penetrating peptide interactions with lipid membranes Article de journal Peter W D'Amore; Christelle Mansuy; Marie Beranger; Olivier Buriez; Eric Labbe; Pierluca Messina; Solange Lavielle; Gerard Chassaing Abstracts of Papers of the American Chemical Society, 243 , 2012. @article{RID:0226140251298-39,
title = {Electrochemical studies of cell penetrating peptide interactions with lipid membranes},
author = {Peter W D'Amore and Christelle Mansuy and Marie Beranger and Olivier Buriez and Eric Labbe and Pierluca Messina and Solange Lavielle and Gerard Chassaing},
year = {2012},
date = {2012-01-01},
journal = {Abstracts of Papers of the American Chemical Society},
volume = {243},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
Electrochemistry of a Ferrocene-Grafted Cell-Penetrating Peptide Article de journal Pierluca Messina; Géraldine Hallais; Eric Labbé; Marie Béranger; Gérard Chassaing; Solange Lavielle; Christelle Mansuy; Olivier Buriez; Christian Amatore Electrochimica Acta, 80 , p. 180-186, 2012. @article{Messina:2012a,
title = {Electrochemistry of a Ferrocene-Grafted Cell-Penetrating Peptide},
author = {Pierluca Messina and G\'{e}raldine Hallais and Eric Labb\'{e} and Marie B\'{e}ranger and G\'{e}rard Chassaing and Solange Lavielle and Christelle Mansuy and Olivier Buriez and Christian Amatore},
doi = {10.1016/j.electacta.2012.06.119},
year = {2012},
date = {2012-04-01},
journal = {Electrochimica Acta},
volume = {80},
pages = {180-186},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
Ferrocenyl catechols: Synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells Article de journal Y L K Tan; P Pigeon; S Top; E Labbé; O Buriez; E A Hillard; A Vessières; C Amatore; W K Leong; G Jaouen Dalton Transactions, 41 (25), p. 7537–7549, 2012. @article{Tan:2012,
title = {Ferrocenyl catechols: Synthesis, oxidation chemistry and anti-proliferative effects on MDA-MB-231 breast cancer cells},
author = {Y L K Tan and P Pigeon and S Top and E Labb\'{e} and O Buriez and E A Hillard and A Vessi\`{e}res and C Amatore and W K Leong and G Jaouen},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-84862232784&doi=10.1039%2fc2dt30700f&partnerID=40&md5=45db7f469e25a5ee6075e706de5e52a9},
doi = {10.1039/c2dt30700f},
year = {2012},
date = {2012-01-01},
journal = {Dalton Transactions},
volume = {41},
number = {25},
pages = {7537--7549},
abstract = {The synthesis and anti-tumoral properties of a series of compounds possessing a ferrocenyl group tethered to a catechol via a conjugated system is presented. On MDA-MB-231 breast cancer cell lines, the catechol compounds display a similar or greater anti-proliferative potency (IC 50 values ranging from 0.48-1.21 μM) than their corresponding phenolic analogues (0.57-12.7 μM), with the highest activity found for species incorporating the [3]ferrocenophane motif. On the electrochemical timescale, phenolic compounds appear to oxidize to the quinone methide, while catechol moieties form the o-quinone by a similar mechanism. Chemical oxidation of selected compounds with Ag 2O confirms this interpretation and demonstrates the probable involvement of such oxidative metabolites in the in vitro activity of these species. © 2012 The Royal Society of Chemistry.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
The synthesis and anti-tumoral properties of a series of compounds possessing a ferrocenyl group tethered to a catechol via a conjugated system is presented. On MDA-MB-231 breast cancer cell lines, the catechol compounds display a similar or greater anti-proliferative potency (IC 50 values ranging from 0.48-1.21 μM) than their corresponding phenolic analogues (0.57-12.7 μM), with the highest activity found for species incorporating the [3]ferrocenophane motif. On the electrochemical timescale, phenolic compounds appear to oxidize to the quinone methide, while catechol moieties form the o-quinone by a similar mechanism. Chemical oxidation of selected compounds with Ag 2O confirms this interpretation and demonstrates the probable involvement of such oxidative metabolites in the in vitro activity of these species. © 2012 The Royal Society of Chemistry. |
2011
|
Electrochemical Analysis of the Interactions and Reactivity of Ferrocene-Based Drugs with a Lipid Environment: A Qualitative Overview Article de journal O Mertins; P Messina; E Labbe; V Vivier; S Arbault; F Lemaitre; O Buriez; C Amatore Inorganica Chimica Acta, 374 (1), p. 59-68, 2011, ISSN: 0020-1693. @article{RN24b,
title = {Electrochemical Analysis of the Interactions and Reactivity of Ferrocene-Based Drugs with a Lipid Environment: A Qualitative Overview},
author = {O Mertins and P Messina and E Labbe and V Vivier and S Arbault and F Lemaitre and O Buriez and C Amatore},
doi = {10.1016/j.ica.2011.04.030},
issn = {0020-1693},
year = {2011},
date = {2011-01-01},
journal = {Inorganica Chimica Acta},
volume = {374},
number = {1},
pages = {59-68},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
Electrochemistry at gold nanoparticles deposited on dendrimers assemblies adsorbed onto gold and platinum surfaces Article de journal Ping-Ping Fang; Olivier Buriez; Eric Labbe; Zhong-Qun Tian; Christian Amatore Journal of Electroanalytical Chemistry, 659 (1), p. 76-82, 2011. @article{RID:0721150706477-20b,
title = {Electrochemistry at gold nanoparticles deposited on dendrimers assemblies adsorbed onto gold and platinum surfaces},
author = {Ping-Ping Fang and Olivier Buriez and Eric Labbe and Zhong-Qun Tian and Christian Amatore},
year = {2011},
date = {2011-01-01},
journal = {Journal of Electroanalytical Chemistry},
volume = {659},
number = {1},
pages = {76-82},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
Kinetic investigations of the electrochemical bromination of peracetylated d-glucal in organic solvents Article de journal D Šegan; R D Vukićević; S Šegan; N Sojic; O Buriez; D Manojlović Electrochimica Acta, 56 (27), p. 9968–9972, 2011. @article{Segan:2011,
title = {Kinetic investigations of the electrochemical bromination of peracetylated d-glucal in organic solvents},
author = {D \v{S}egan and R D Vuki\'{c}evi\'{c} and S \v{S}egan and N Sojic and O Buriez and D Manojlovi\'{c}},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-80054931632&doi=10.1016%2fj.electacta.2011.08.085&partnerID=40&md5=c6c44f6eb1b98fe587e4e5ac623bb3d4},
doi = {10.1016/j.electacta.2011.08.085},
year = {2011},
date = {2011-01-01},
journal = {Electrochimica Acta},
volume = {56},
number = {27},
pages = {9968--9972},
abstract = {Cyclic voltammetry and ultramicroelectrodes were used to investigate the kinetic aspects of the electrochemical bromination of 3,4,6-tri-O-acetyl-d- glucal (1) in acetonitrile (AN), dichloromethane (DCM), and dimethylsulfoxide (DMSO). Qualitative and quantitative results, determined notably from the kinetic parameter [glucal]/v representing the competition between glucal concentration and time, clearly showed that glucal bromination depended on the nature of both the solvent and the in situ electrogenerated reactive brominated species (Br2 or Br3 -) obtained from the oxidation of a bromide salt. It was especially shown that Br2 reacted more rapidly than Br3 - towards (1). On the other hand, the reactivity of both brominated species appeared to follow the solvent polarity order since the highest reactivity was obtained in DMSO whereas the lowest one was found in DCM. © 2011 Elsevier Ltd. All Rights Reserved.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
Cyclic voltammetry and ultramicroelectrodes were used to investigate the kinetic aspects of the electrochemical bromination of 3,4,6-tri-O-acetyl-d- glucal (1) in acetonitrile (AN), dichloromethane (DCM), and dimethylsulfoxide (DMSO). Qualitative and quantitative results, determined notably from the kinetic parameter [glucal]/v representing the competition between glucal concentration and time, clearly showed that glucal bromination depended on the nature of both the solvent and the in situ electrogenerated reactive brominated species (Br2 or Br3 -) obtained from the oxidation of a bromide salt. It was especially shown that Br2 reacted more rapidly than Br3 - towards (1). On the other hand, the reactivity of both brominated species appeared to follow the solvent polarity order since the highest reactivity was obtained in DMSO whereas the lowest one was found in DCM. © 2011 Elsevier Ltd. All Rights Reserved. |
Tailoring Au-core Pd-shell Pt-cluster nanoparticles for enhanced electrocatalytic activity Article de journal P -P Fang; S Duan; X -D Lin; J R Anema; J -F Li; O Buriez; Y Ding; F -R Fan; D -Y Wu; B Ren; Z L Wang; C Amatore; Z -Q Tian Chemical Science, 2 (3), p. 531–539, 2011. @article{Fang:2011a,
title = {Tailoring Au-core Pd-shell Pt-cluster nanoparticles for enhanced electrocatalytic activity},
author = {P -P Fang and S Duan and X -D Lin and J R Anema and J -F Li and O Buriez and Y Ding and F -R Fan and D -Y Wu and B Ren and Z L Wang and C Amatore and Z -Q Tian},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-79952659758&doi=10.1039%2fc0sc00489h&partnerID=40&md5=3667f2602024e8684887359041c3e9d7},
doi = {10.1039/c0sc00489h},
year = {2011},
date = {2011-01-01},
journal = {Chemical Science},
volume = {2},
number = {3},
pages = {531--539},
abstract = {We have rationally synthesized and optimized catalytic nanoparticles consisting of a gold core, covered by a palladium shell, onto which platinum clusters are deposited (Au@Pd@Pt NPs). The amount of Pt and Pd used is extremely small, yet they show unusually high activity for electrooxidation of formic acid. The optimized structure has only 2 atomic layers of Pd and a half-monolayer equivalent of Pt (θPt ≈ 0.5) but a further increase in the loading of Pd or Pt will actually reduce catalytic activity, inferring that a synergistic effect exists between the three different nanostructure components (sphere, shell and islands). A combined electrochemical, surface-enhanced Raman scattering (SERS) and density functional theory (DFT) study of formic acid and CO oxidation reveals that our core-shell-cluster trimetallic nanostructure has some unique electronic and morphological properties, and that it could be the first in a new family of nanocatalysts possessing unusually high chemical reactivity. Our results are immediately applicable to the design of catalysts for direct formic acid fuel cells (DFAFCs). © The Royal Society of Chemistry 2011.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
We have rationally synthesized and optimized catalytic nanoparticles consisting of a gold core, covered by a palladium shell, onto which platinum clusters are deposited (Au@Pd@Pt NPs). The amount of Pt and Pd used is extremely small, yet they show unusually high activity for electrooxidation of formic acid. The optimized structure has only 2 atomic layers of Pd and a half-monolayer equivalent of Pt (θPt ≈ 0.5) but a further increase in the loading of Pd or Pt will actually reduce catalytic activity, inferring that a synergistic effect exists between the three different nanostructure components (sphere, shell and islands). A combined electrochemical, surface-enhanced Raman scattering (SERS) and density functional theory (DFT) study of formic acid and CO oxidation reveals that our core-shell-cluster trimetallic nanostructure has some unique electronic and morphological properties, and that it could be the first in a new family of nanocatalysts possessing unusually high chemical reactivity. Our results are immediately applicable to the design of catalysts for direct formic acid fuel cells (DFAFCs). © The Royal Society of Chemistry 2011. |
2010
|
Aminocyclopropanes as precursors of endoperoxides with antimalarial activity Article de journal C Madelaine; O Buriez; B Crousse; I Florent; P Grellier; P Retailleau; Y Six Organic and Biomolecular Chemistry, 8 (24), p. 5591–5601, 2010. @article{Madelaine:2010,
title = {Aminocyclopropanes as precursors of endoperoxides with antimalarial activity},
author = {C Madelaine and O Buriez and B Crousse and I Florent and P Grellier and P Retailleau and Y Six},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-78649506056&doi=10.1039%2fc0ob00308e&partnerID=40&md5=f96ad4b84369abf15d7e7587373db1d1},
doi = {10.1039/c0ob00308e},
year = {2010},
date = {2010-01-01},
journal = {Organic and Biomolecular Chemistry},
volume = {8},
number = {24},
pages = {5591--5601},
abstract = {This contribution describes the synthesis of several novel bicyclic α-amino endoperoxides, including CF3-substituted compounds, prepared by the aerobic electrochemical oxidation of a family of bicyclic aminocyclopropanes. These, in turn, are readily synthesised by a titanium-mediated intramolecular cyclopropanation process (Kulinkovich-de Meijere reaction), starting from N-alkenyl amides that contain a vic-disubstituted double bond, with high diastereoselectivity. An evaluation of the biological activities of several of the molecules produced, against the parasite Plasmodium falciparum, is also presented. © 2010 The Royal Society of Chemistry.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
This contribution describes the synthesis of several novel bicyclic α-amino endoperoxides, including CF3-substituted compounds, prepared by the aerobic electrochemical oxidation of a family of bicyclic aminocyclopropanes. These, in turn, are readily synthesised by a titanium-mediated intramolecular cyclopropanation process (Kulinkovich-de Meijere reaction), starting from N-alkenyl amides that contain a vic-disubstituted double bond, with high diastereoselectivity. An evaluation of the biological activities of several of the molecules produced, against the parasite Plasmodium falciparum, is also presented. © 2010 The Royal Society of Chemistry. |
Electrochemical bromination of peracetylated d-glucal: Effect of DMSO on chemoselectivity Article de journal I Damljanović; M Vukićević; D Manojlović; N Sojic; O Buriez; R D Vukićević Electrochimica Acta, 55 (3), p. 965–969, 2010. @article{Damljanovic:2010,
title = {Electrochemical bromination of peracetylated d-glucal: Effect of DMSO on chemoselectivity},
author = {I Damljanovi\'{c} and M Vuki\'{c}evi\'{c} and D Manojlovi\'{c} and N Sojic and O Buriez and R D Vuki\'{c}evi\'{c}},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-70849109027&doi=10.1016%2fj.electacta.2009.09.057&partnerID=40&md5=d753bdeed3ddcaff44a42c2a332df812},
doi = {10.1016/j.electacta.2009.09.057},
year = {2010},
date = {2010-01-01},
journal = {Electrochimica Acta},
volume = {55},
number = {3},
pages = {965--969},
abstract = {The electrochemical bromination of 3,4,6-tri-O-acetyl-d-glucal (1) has been investigated in dimethyl sulfoxide (DMSO) by cyclic voltammetry and preparative-scale electrolyses. In this solvent, the bromination involves a bromine-DMSO complex of the type [DMSO-Br]+Br- whose reactivity towards 1 was clearly evidenced by cyclic voltammetry. Importantly, only the monobrominated glucose and mannose derivatives were obtained from electrolyses. This specific behavior was attributed to the nucleophilicity of DMSO that may react with the oxocarbenium intermediate preventing thus a possible second bromination of the transient species. The gluco/manno ratio, roughly equal to 30/70, indicated an electrophilic attack by [DMSO-Br]+Br- preferentially from the β side of the starting glycal for steric reasons. The treatment of the crude product obtained after the end of the electrolyses with acetic anhydride allowed the preparation of derivatives in which the anomeric carbon bears an acetoxy group. Based on both the cyclic voltammetry experiments and preparative-scale electrolyses, a mechanism is proposed for the bromination of peracetylated d-glucal in DMSO. These new and original results are of high interest in carbohydrate chemistry and especially for the preparation of new valuable oligosaccharides. © 2009 Elsevier Ltd. All rights reserved.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
The electrochemical bromination of 3,4,6-tri-O-acetyl-d-glucal (1) has been investigated in dimethyl sulfoxide (DMSO) by cyclic voltammetry and preparative-scale electrolyses. In this solvent, the bromination involves a bromine-DMSO complex of the type [DMSO-Br]+Br- whose reactivity towards 1 was clearly evidenced by cyclic voltammetry. Importantly, only the monobrominated glucose and mannose derivatives were obtained from electrolyses. This specific behavior was attributed to the nucleophilicity of DMSO that may react with the oxocarbenium intermediate preventing thus a possible second bromination of the transient species. The gluco/manno ratio, roughly equal to 30/70, indicated an electrophilic attack by [DMSO-Br]+Br- preferentially from the β side of the starting glycal for steric reasons. The treatment of the crude product obtained after the end of the electrolyses with acetic anhydride allowed the preparation of derivatives in which the anomeric carbon bears an acetoxy group. Based on both the cyclic voltammetry experiments and preparative-scale electrolyses, a mechanism is proposed for the bromination of peracetylated d-glucal in DMSO. These new and original results are of high interest in carbohydrate chemistry and especially for the preparation of new valuable oligosaccharides. © 2009 Elsevier Ltd. All rights reserved. |
Synthesis and electrochemical study of an original copper(II)-capped salen-cyclodextrin complex Article de journal E Deunf; E Zaborova; S Guieu; Y Blériot; J -N Verpeaux; O Buriez; M Sollogoub; C Amatore European Journal of Inorganic Chemistry, (29), p. 4720–4727, 2010. @article{Deunf:2010,
title = {Synthesis and electrochemical study of an original copper(II)-capped salen-cyclodextrin complex},
author = {E Deunf and E Zaborova and S Guieu and Y Bl\'{e}riot and J -N Verpeaux and O Buriez and M Sollogoub and C Amatore},
url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-78349284824&doi=10.1002%2fejic.200901208&partnerID=40&md5=c49a97fb828e67d03424443181136cc8},
doi = {10.1002/ejic.200901208},
year = {2010},
date = {2010-01-01},
journal = {European Journal of Inorganic Chemistry},
number = {29},
pages = {4720--4727},
abstract = {A new metallocapped cyclodextrin (CD) was synthesized by the regioselective debenzylation, induced by diisobutylaluminium hydride (DIBAL-H), of perbenzylated cyclodextrins. This reaction allowed for the efficient preparation of an unprecedented CD-salen type copper(II) complex. The electrochemical behavior of both the bound and unbound CD-salen compounds was investigated by cyclic voltammetry. Notably, it was shown that the presence of tert-butyl groups at the ortho- and para-positions of the salen aromatic rings stabilized the copper(II) phenoxyl radical species that was generated upon the one-electron oxidation of the starting compound. Importantly, this stabilization remained effective when the salen-type ligand was covalently attached to the CD. This allowed for investigations of the reactivity of the copper(II) phenoxyl radical complex towards a primary alcohol to be performed by cyclic voltammetry. This reaction can be considered as mimicking the behavior of galactose oxidase. However, under these conditions, no reactivity was observed in the presence of benzyl alcohol. This may be due to distortion, either of the initially square planar salen ligand after its grafting to the CD primary face, and/or of the CD itself. On the other hand, the electrochemical reduction of the un-grafted copper(II) salen-type ligand led to a transient anionic species that exhibited significant stability on the time-scale of the slow cyclic voltammetry measurement in the absence of the CD, but was unstable in the presence of the CD. In the latter case, it was demonstrated that the anionic species was protonated by the CD. Importantly, this protonation was not fast enough to prevent catalytic activation of iodomethane by the electro-generated copper(I)-capped salen CD complex. A new metallocapped cyclodextrin was synthesized by a regioselective debenzylation reaction that was induced by diisobutylaluminium hydride (DIBAL-H). The electrochemical investigation of this original complex demonstrated that grafting of a copper salen-type complex to a cyclodextrin leads to changes in the reactivity of the intermediary species. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
A new metallocapped cyclodextrin (CD) was synthesized by the regioselective debenzylation, induced by diisobutylaluminium hydride (DIBAL-H), of perbenzylated cyclodextrins. This reaction allowed for the efficient preparation of an unprecedented CD-salen type copper(II) complex. The electrochemical behavior of both the bound and unbound CD-salen compounds was investigated by cyclic voltammetry. Notably, it was shown that the presence of tert-butyl groups at the ortho- and para-positions of the salen aromatic rings stabilized the copper(II) phenoxyl radical species that was generated upon the one-electron oxidation of the starting compound. Importantly, this stabilization remained effective when the salen-type ligand was covalently attached to the CD. This allowed for investigations of the reactivity of the copper(II) phenoxyl radical complex towards a primary alcohol to be performed by cyclic voltammetry. This reaction can be considered as mimicking the behavior of galactose oxidase. However, under these conditions, no reactivity was observed in the presence of benzyl alcohol. This may be due to distortion, either of the initially square planar salen ligand after its grafting to the CD primary face, and/or of the CD itself. On the other hand, the electrochemical reduction of the un-grafted copper(II) salen-type ligand led to a transient anionic species that exhibited significant stability on the time-scale of the slow cyclic voltammetry measurement in the absence of the CD, but was unstable in the presence of the CD. In the latter case, it was demonstrated that the anionic species was protonated by the CD. Importantly, this protonation was not fast enough to prevent catalytic activation of iodomethane by the electro-generated copper(I)-capped salen CD complex. A new metallocapped cyclodextrin was synthesized by a regioselective debenzylation reaction that was induced by diisobutylaluminium hydride (DIBAL-H). The electrochemical investigation of this original complex demonstrated that grafting of a copper salen-type complex to a cyclodextrin leads to changes in the reactivity of the intermediary species. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
2009
|
A 3 Ferrocenophane Polyphenol Showing a Remarkable Antiproliferative Activity on Breast and Prostate Cancer Cell Lines Article de journal Damian Plazuk; Anne Vessieres; Elizabeth A Hillard; Olivier Buriez; Eric Labbe; Pascal Pigeon; Marie-Aude Plamont; Christian Amatore; Janusz Zakrzewski; Gerard Jaouen Journal of Medicinal Chemistry, 52 (15), p. 4964-4967, 2009. @article{RID:0721150706477-28b,
title = {A 3 Ferrocenophane Polyphenol Showing a Remarkable Antiproliferative Activity on Breast and Prostate Cancer Cell Lines},
author = {Damian Plazuk and Anne Vessieres and Elizabeth A Hillard and Olivier Buriez and Eric Labbe and Pascal Pigeon and Marie-Aude Plamont and Christian Amatore and Janusz Zakrzewski and Gerard Jaouen},
year = {2009},
date = {2009-01-01},
journal = {Journal of Medicinal Chemistry},
volume = {52},
number = {15},
pages = {4964-4967},
keywords = {},
pubstate = {published},
tppubtype = {article}
}
|
