Publications by authors named "Fabienne Berrée"

15 Publications

  • Page 1 of 1

Circularly Polarized Fluorescent Helicene-Boranils: Synthesis, Photophysical and Chiroptical Properties.

Chemistry 2021 May 22;27(29):7959-7967. Epub 2021 Apr 22.

Univ Rennes, CNRS, ISCR-UMR 6226, Université de Rennes 1, Campus de Beaulieu, 35042, Rennes Cedex, France.

Mono- and di-boranil-substituted helicenes were prepared by BF -borylation of the corresponding anils, readily synthesized by condensation of 2-amino- and 2,15-diamino-helicenes with 4-(diethylamino)salicylaldehyde. After enantiomeric resolution using HPLC, their chiroptical properties including circularly polarized fluorescence in solution and in PMMA films were investigated and rationalized with the help of NMR, X-ray and quantum-chemical calculations.
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http://dx.doi.org/10.1002/chem.202100356DOI Listing
May 2021

Copper-Mediated Synthesis of ()-1-Azido and ()-1,2-Diazido Alkenes from 1-Alkene-1,2-diboronic Esters: An Approach to Mono- and 1,2-Di-(1,2,3-Triazolyl)-Alkenes and Fused Bis-(1,2,3-Triazolo)-Pyrazines.

J Org Chem 2020 Dec 5;85(23):15104-15115. Epub 2020 Nov 5.

Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France.

A stereoselective and convenient route has been demonstrated to access ()-1,2-diazido alkenes from the corresponding 1,2-diboronic esters a copper-mediated reaction with sodium azide. Alternately, mono-functionalization was regioselectively carried out with trimethylsilyl azide as an azidation reactant. The conversion of bis-azides to the corresponding bis-triazoles can be readily achieved in the presence of copper sulfate and sodium ascorbate, while the modification of the catalytic system opened a new convenient route to bis-triazolo-pyrazines, a new class of fused heterocycles.
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http://dx.doi.org/10.1021/acs.joc.0c01980DOI Listing
December 2020

Boron Effect on Sugar-Based Organogelators.

Chemistry 2020 Nov 29;26(61):13927-13934. Epub 2020 Sep 29.

Ecole Nationale Supérieure de Chimie de Rennes, CNRS, ISCR-UMR6226, Université de Rennes, 35000, Rennes, France.

The reaction of several alkylglucosides with phenyl boronic acid permitted easy access to a series of alkylglucoside phenyl boronate derivatives. This type of compound has structures similar to those of known benzylidene glucoside organogelators except for the presence of a boronate function in place of the acetal one. Low to very low concentrations of these amphiphilic molecules produced gelation of several organic solvents. The rheological properties of the corresponding soft materials characterized them as elastic solids. They were further characterized by SEM to obtain more information on their morphologies and by SAXS to determine the type of self-assembly involved within the gels. The sensitivity of the boronate function towards hydrolysis was also investigated. We demonstrated that a small amount of water (5 % v/v) was sufficient to disrupt the organogels leading to the original alkylglucoside and phenyl boronic acid; an important difference with the stable benzylidene-based organogelators. Such water-sensitive boronated organogelators could be suitable substances for the preparation of smart soft material for topical drug delivery.
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http://dx.doi.org/10.1002/chem.202001970DOI Listing
November 2020

Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and Arylnitroso Compounds.

J Org Chem 2020 Apr 2;85(8):5173-5182. Epub 2020 Apr 2.

Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)-UMR 6226, F-35000 Rennes, France.

Complimentary to classical hydroboration and boron-Wittig reactions, a new, efficient access to cyclic 1,3-dienyl boronic esters has been developed diene or triene metathesis. Subsequently, fused pyrroles were synthesized with a broad substrate scope from the reaction of cyclic 1,3-dienyl boronic esters with arylnitroso compounds using a one-pot hetero-Diels-Alder/ring contraction sequence.
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http://dx.doi.org/10.1021/acs.joc.9b03214DOI Listing
April 2020

Ene reactions of 2-borylated α-methylstyrenes: a practical route to 4-methylenechromanes and derivatives.

Org Biomol Chem 2019 06;17(23):5789-5800

Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France.

4-Methylenechromanes were prepared via a three-step process from 2-borylated α-methylstyrenes. This sequence is based on a key glyoxylate-ene reaction catalyzed by scandium(iii) triflate. The resulting γ-hydroxy boronates, which cyclise to seven-membered homologues of benzoxaborole on silica gel, were cleanly oxidized with sodium perborate, and then cyclised under Mitsunobu conditions. Additionally, several further functional transformations of 4-methylenechromanes or their precursors were carried out to illustrate the synthetic potential of these intermediates.
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http://dx.doi.org/10.1039/c9ob00963aDOI Listing
June 2019

Synthesis of Polysubstituted Isoquinolines and Related Fused Pyridines from Alkenyl Boronic Esters via a Copper-Catalyzed Azidation/Aza-Wittig Condensation Sequence.

J Org Chem 2018 01 5;83(2):843-853. Epub 2018 Jan 5.

Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226 , F-35000 Rennes, France.

An efficient and straightforward synthesis of isoquinolines is reported from internal alkenyl boronic esters, easily prepared from the corresponding 1,2-bis(boronates), via a sequential copper-catalyzed azidation/aza-Wittig condensation. This synthetic method has been used to synthesize quinisocaine, a topical anesthetic used for the treatment of pain and pruritus, and further extended to thieno[2,3-c]pyridines by using 2-thiophenecarboxaldehyde as coupling partner in the first step.
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http://dx.doi.org/10.1021/acs.joc.7b02831DOI Listing
January 2018

Synthesis of Carbo[6]helicene Derivatives Grafted with Amino or Aminoester Substituents from Enantiopure [6]Helicenyl Boronates.

J Org Chem 2018 01 21;83(1):484-490. Epub 2017 Dec 21.

Univ Rennes, CNRS, ISCR [(Institut des Sciences Chimiques de Rennes)] - UMR 6226 , F-35000, Rennes, France.

Enantiopure carbo[6]helicenyl boronates were synthesized using a photocyclization reaction as the key step. These compounds were further converted to various amino derivatives using copper-catalyzed azidation or amination and reductive alkylation of benzylazide by a helicenyl dichloroborane. Asymmetric Petasis condensation with glyoxylic acid and morpholine controlled by the helical chirality afforded the corresponding amino esters.
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http://dx.doi.org/10.1021/acs.joc.7b02619DOI Listing
January 2018

Synthesis of 1-Amino-1H-Indenes via a Sequential Suzuki-Miyaura Coupling/Petasis Condensation Sequence.

J Org Chem 2017 02 23;82(3):1803-1811. Epub 2017 Jan 23.

Institut des Sciences Chimiques de Rennes, UMR 6226, CNRS-Université de Rennes 1 , 263, Avenue du Général Leclerc, Campus de Beaulieu, 35042 Rennes Cedex, France.

An efficient and straightforward synthesis of 1-amino-1H-indenes is reported from 1,2-bis(boronates) via a sequential Suzuki-Miyaura coupling/Petasis cyclization reaction. Starting from the same monoboronic ester intermediates, an intermolecular version of this approach also afforded (Z)-α,β-unsaturated amino esters in moderate to good yields.
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http://dx.doi.org/10.1021/acs.joc.6b02549DOI Listing
February 2017

Synthesis and evaluation of 1,2-trans alkyl galactofuranoside mimetics as mycobacteriostatic agents.

Org Biomol Chem 2015 May;13(17):4940-52

Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, France.

The simple octyl β-D-galactofuranoside was previously described as a good bacteriostatic agent against Mycobacterium smegmatis, a non-pathogenic model of M. tuberculosis. In order to decipher its mechanism of action, STD NMR on whole M. smegmatis cells was implemented. It outlined the crucial role of the alkyl chain and the possibility of modulation on the furanosyl entity. Then, 16 new alkyl furanosides were synthesized in order to optimize the mycobacteriostatic activity. They all present the pending alkyl chain in a 1,2-trans configuration relative to the sugar ring. Three families were studied that differ by a substituent on the primary position of the galactofuranose ring, the series or the pending alkyl chain. Four of these neofuranosides showed growth inhibition inferior to the parent octyl β-D-galactofuranoside. Double alkyl chains at C-1 and a polar substituent on the primary position of the furanoside significantly favored the activity. Finally, a mixed biantennary alkyl/aryl β-D-galactofuranoside exhibited the best growth inhibition concentration at 90 μM.
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http://dx.doi.org/10.1039/c5ob00296fDOI Listing
May 2015

Regio- and stereocontrolled access to γ-boronated unsaturated amino esters and derivatives from (Z)-alkenyl 1,2-bis(boronates).

J Org Chem 2014 Jan 23;79(2):783-9. Epub 2013 Dec 23.

Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1 , 263 Avenue du Général Leclerc, Campus de Beaulieu, Bâtiment 10A, 35042 Rennes Cedex, France.

The Borono-Mannich reaction of (Z)-1-alkene-1,2-diboronic esters proceeded regioselectively at the terminal C-B bond to afford (E)-γ-boronated unsaturated amino esters in good yields. These compounds were then subjected to Suzuki couplings for the creation of diversely substituted olefinic amino acid systems. Several other functional transformations were also carried out to illustrate the synthetic utility of the Petasis products.
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http://dx.doi.org/10.1021/jo402237tDOI Listing
January 2014

Synthesis and antibacterial activity of novel neamine derivatives: preponderant role of the substituent position on the neamine core.

Org Biomol Chem 2012 Jun 15;10(24):4720-30. Epub 2012 May 15.

Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes, France.

A series of neamine derivatives were prepared from the cyclic carbonate and sulfate of 1,3,2',6'-tetraazido-3',4',-di-O-acetylneamine. Ring opening reactions with diversely substituted amines result in the formation of the corresponding carbamates or sulfonic acids with good overall yields. The antibacterial activities of the synthesized products against E. coli (DH5α) and S. aureus (RN4220) were evaluated. With isolated single regioisomers, the preponderant effect of the 5-positions of the carbamate substituent on the neamine core was demonstrated.
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http://dx.doi.org/10.1039/c2ob07065kDOI Listing
June 2012

Antiviral effect of ribonuclease conjugated oligodeoxynucleotides targeting the IRES RNA of the hepatitis C virus.

Bioorg Med Chem Lett 2009 Jul 4;19(13):3581-5. Epub 2009 May 4.

Université de Rennes 1, UPRES JE 2311, INSERM U835, Biochimie Pharmaceutique, 2, Avenue du Prof. Léon Bernard, 35043 Rennes, France.

Hepatitis C virus (HCV) translation initiation is mediated by a highly structured and conserved RNA, termed the Internal Ribosome Entry Site (IRES), located at the 5'-end of its single stranded RNA genome. It is a key target for the development of new antiviral compounds. Here we made use of the recently developed HCV cell culture system to test the antiviral activity of artificial ribonucleases consisting of imidazole(s) linked to antisense oligodeoxynucleotides targeting the HCV IRES. Results from the cell culture model indicate that the naked antisense oligodeoxynucleotide displayed an efficient antiviral activity. Despite the increased activity observed with the addition of imidazole moieties when tested with the cell-free system, it appears that these improvements were not reproduced in the cellular model.
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http://dx.doi.org/10.1016/j.bmcl.2009.04.139DOI Listing
July 2009

Targeted inhibition of the hepatitis C internal ribosomal entry site genomic RNA with oligonucleotide conjugates.

Nucleic Acids Res 2007 5;35(20):6778-87. Epub 2007 Oct 5.

Biochimie Pharmaceutique, Inserm U835, Upres JE 2311, Université de Rennes 1, France.

Hepatitis C is a major public health concern, with an estimated 170 million people infected worldwide and an urgent need for new drug development. An attractive therapeutic approach is to prevent the 'cap-independent' translation initiation of the viral proteins by interfering with both the structure and function of the hepatitis C viral internal ribosomal entry site (HCV IRES). Towards this goal, we report the design, synthesis and purification of novel bi-functional molecules containing DNA or RNA antisenses attached to functional groups performing RNA hydrolysis. These 5' or 3'-coupled conjugates bind the HCV IRES with affinity and specificity and elicit targeted hydrolysis of the viral genomic RNA after short (1 h) incubation at low (500 nM) concentration at 37 degrees C in vitro. Additional secondary cleavage sites are induced and their mapping within the RNA structure indicates that functional domains IIIb-e are excised from the IRES that, based on cryo-EM studies, becomes incapable of binding the small ribosomal subunit and initiation factor 3 (eIF3). All these molecules inhibit, in a dose-dependent manner, the 'IRES-dependent' translation in vitro. The 5'-coupled imidazole conjugate reduces viral protein synthesis by half at a 300 nM concentration (IC50), corresponding to a 4-fold increase of activity when compared to the naked oligonucleotide. These new conjugates are now being tested for activity on infected hepatic cell lines.
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http://dx.doi.org/10.1093/nar/gkm770DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2175329PMC
December 2007

Boronated enynes as versatile sources of stereodefined and skeletally diverse molecules.

Org Lett 2007 Apr 5;9(9):1717-20. Epub 2007 Apr 5.

Ingéniérie Chimique et Molécules pour le Vivant, Sciences Chimiques de Rennes, UMR 6226, Rennes CEDEX, France.

[reaction: see text] The application of a one-pot palladium-catalyzed cycloisomerization of enynes 1/Diels-Alder cycloaddition/allylboration sequence efficiently generates tricyclic structures with complete control of the four stereogenic centers. Ruthenium and platinum catalysts perform distinct transformations providing other isomeric boron-substituted cyclic compounds.
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http://dx.doi.org/10.1021/ol070400sDOI Listing
April 2007

Synthesis of Anisolylated Aspartyl and Glutamyl Tripeptides.

J Org Chem 1996 Jan;61(2):715-721

Department of Chemistry, University of California, Berkeley, California 94720.

A process has been developed for transforming the beta-carboxyl of aspartate and the gamma-carboxyl of glutamate into anisolyl ketones. These ketones are occasional byproducts in peptide synthesis, resulting from deprotection or resin-removal processes in the presence of anisole as a scavenger. The ketone amino acids have been incorporated in a tripeptide by coupling with CBMIT. During peptide bond formation the keto group of the glutamyl residue required protection, which was provided as the ethylene dithioketal.
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http://dx.doi.org/10.1021/jo951754cDOI Listing
January 1996