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Accueil > Personnels > MESSAOUDI Samir

MESSAOUDI Samir

DIRECTEUR DE RECHERCHE CNRS (DR2)
Responsable de l’équipe CosMIT
Faculté de Pharmacie,
Université Paris-Sud 11
Equipe chimie Thérapeutique, Laboratoire BioCIS UMR 8076,
tel : +33.1.46.83.56.83
fax : +33.1.46.83.57.28
samir.messaoudi@u-psud.fr


Samir MESSAOUDI is a Director of Research at CNRS since 2017. He started learning chemistry (DEA, 2001) under the supervision of Prof. Pascale Moreau at Blaise Pascal University (Clermont Ferrand, France) and completed his PhD in 2004 under the supervision of Prof. Michelle Prudhomme (SEESIB, UMR 6296, Clermont Ferrand) on the synthesis of Rebecamycine, Staurosporine and Granulatimide analogues as anticancer agents. He then worked as a post-doctoral fellow with Prof. David. J. Aitken working on the total synthesis of Microsclerodermin C. Following a second post-doctoral fellowship working with Dr. Mouad Alami/ Prof. J.-D. Brion at the Pharmacy Faculty of Châtenay Malabry (Paris Sud University), he was appointed CNRS Researcher (2007) and joined the group of "Therapeutic Chemistry" at the University of Paris 11. He obtained his Habilitation diploma (HDR) in January 2011, working mainly on the transition-metal catalyzed C-C and C-heteroatom bond forming methodologies, Diversity-Oriented Synthesis (DOS) in sugars and heterocycles, as well as the preparation of molecules and molecular scaffolds of biological and therapeutic interest (Hsp90 inhibitors and vascular disrupting agents).

Samir is a member of the CoNRS (Comité National CNRS, Section 16, INC) for the period 2012-2016.


AWARD
/ He was the recipient of the "Prix d’Encouragement à la Recherche en Chimie Thérapeutique" award of the French Therapeutic Chemistry Society and SERVIER laboratories in 2012.

 RESEARCH INTERESTS

Heterocycles simultaneously constitute one of the most important building blocks in medicinal chemistry and one of the most challenging molecular scaffolds to functionalize. Functionalization of heterocycles under transition metal catalysis is of great interest, because it allows a direct access to original organic molecules, which are potentially useful for the discovery of new drugs. In this context, we are interested in a wide number of different transformations. these include :

 GLYCOCHEMISTRY UNDER TRANSITION-METAL CATALYSIS-

As a coordinator, Sam Messaoudi is the recipient of the ANR grants from the National Research Agency :
CarNuCat : 2015-2017
SelfSuCHi : 2018-2022

The Glycochemsitry topic deals with the use transition metal-catalyzed approaches to explore new ways to functionalize glycosides. The chemistry in this proposal involves the development of a series of processes concerning N-, S- , O- or C-glycosidic bonds functionalization under transition metal catalysis.

Based on the successful outcome of this project, an unlimited number of organic transformations will be possible in the future, and the development of such new sustainable methodologies will make a tremendous impact into routine organic synthesis of glycoconjugates and into selective late-stage modification of pharmaceuticals. This conceptually novel approach would provide chemists in both the academic and industrial worlds with new disconnection strategies that give access to molecules with original structures and properties in a simple, efficient, and ecological manner.

 C-HETEROATOM BONDS FORMING METHODOLOGIES

The design of new methods for the formation of carbon-nitrogen bonds. This works involves the use of metal catalysts, usually based on palladium and copper. We reported an efficient and general metal-catalyzed coupling reaction between 3-bromocoumarins, 3-bromoquinolin-2(1H)-ones, 3-iodo-2H-chromenes and 4-haloquinolones with a variety of nitrogen containing nucleophiles (azole, amide, lactam, sulfonamide, aniline, amine, and urea)

 C-C BONDS FORMING METHODOLOGIES : C-H Activations and Decarboxylative Goossen couplings

Within the field of heterocycles C-H functionalization, the majority of work has focused on a site selective C–H arylation of free-(NH2) adenines and application to the synthesis of 6,8-disubstituted adenines. The process based on the use of Pd(OH)2/C as
the catalyst and a stoichiometric amount of CuI under ligandless conditions allows the coupling to proceed with a variety of aryl halides, including for the first time cheaper and less reactive
aryl chlorides.

 TARGETING THE HEAT SHOCK PROTEIN 90 (hsp90) DESIGN OF NEW NOVOBIOCIN ANALOGUES

Hsp90 is an emerging therapeutic target of interest for the treatment of cancer and other diseases. As a chaperone protein, hsp90 is essential to ensure the correct conformation, activity, intracellular localization and proteolytic turnover of a range of proteins that are involved in cell growth, differentiation and survival.The hsp90 protein function may be inhibited by molecules competing with ATP binding, thereby freezing the chaperone cycle, which in turn decreases the affinity of hsp90 for client proteins and leads to proteasome-mediated oncogenic client protein degradation. Several structurally distinct hsp90 inhibitors, as single agents or in combination with other cancer drugs, are currently being evaluated for anticancer activity in numerous Phase II and several Phase III clinical trials.

A few years ago, a hypothesis had suggested the presence of two ATP binding sites on the hsp90 protein. The N-terminal ATP-binding pocket of hsp90 is the binding site of the structurally unrelated natural products geldanamycin (GA) and radicicol (RD). The C-terminal domain has been implicated biochemically as the site of a possible second, cryptic ATP-binding site on hsp90. Its contribution to the overall regulation of chaperone function is not clear, but the antibiotic novobiocin has been reported to bind this site and alter the conformation of the chaperone. Although it binds with poor affinity, Nvb destabilizes hsp90 client proteins at high concentrations ( 700 microM). A better understanding of the role of this putative hsp90 C-domain site in regulating the function of the chaperone, as well as its potential as an anticancer drug target, requires further investigations. Advantages of HSP90 inhibitors that target the C-terminal domain (C-terminal inhibitors) include less robust activation of heat shock factor 1 (HSF1), which induces HSP90 transcription. Thus,the identification of more potent site-specific inhibitors is needed and has led the development of specific C-terminal hsp90 inhibitors as potential anticancer drug modalities.

 PUBLICATIONS

2021

102. M. Zhu and S. Messaoudi "Diastereoselective Decarboxylative Alkynylation of Anomeric Carboxylic Acids Using Cu\/Photoredox Dual Catalysis" ACS Catalysis 2021, 11, 6334-6342.
link

101. D. Ryzhakov, G. Printz, B. Jacques, S. Messaoudi, F. Dumas, S. Dagorne and F. Le Bideau. "Organo-Catalyzed/Initiated Ring Opening Co-Polymerization of Cyclic Anhydrides and Epoxides : an Emerging Story". Polymer Chem. 2021, . link

100. J. Ghouilem, C. Tran, N. Grimblat, P. Retailleau, M. Alami, V. Gandon, S. Messaoudi. Diastereoselective Pd-Catalyzed Anomeric C(sp3)H Activation : Synthesis of (hetero)aryl C-Glycosides. ACS Catalysis 2021, 11, 1818–1826. link

99. J. Ghouilem, M. de Robichon, F. Le Bideau, A. Ferry, S. Messaoudi, "Emerging organometallic methods for the synthesis of C‐branched (hetero)aryl, alkenyl and alkyl glycosides : C–H functionalization and dual photoredox approaches", Chem. Eur.J 2021, 27, 491-511 . link

2020

98. T. Hadi, C. Ramseyer, T. Gautier, P-S. Bellaye, T. Lopez, A. Schmitt, F. Sarah, S. Yesylevskyy, T. Minervini, R. Douhard, L. Dondaine, L. Proukhnitzky, S. Messaoudi, M. Wendremaire, M. Moreau, F. Neiers, B. Collin, F. Denat, L. Lagrost, C. Garrido, and F. Lirussi, "Lipoproteins LDL versus HDL as nanocarriers to target either cancer cells or macrophages", JCI insight 2020, link

97. M. Zhu, M. Alami, S. Messaoudi, "Room Temperature Pd-Catalyzed Synthesis of 1-(Hetero)aryl Selenoglycosides", Org. Lett. 2020, 22, 6584-6589 . link

96. N. Bennai, N. Ibrahim, J. Marrot, M. Belkadi, M. Alami, E. Magnier, E. Anselmi, S. Messaoudi, "Synthesis of S-Trifluoromethyl S-Arylsulfoximine Thioglycosides through Pd-Catalyzed Migita Cross-Couling", Eur. J. Org. Chem. 2020, 4972-4981. link

95. M. Zhu, M. Alami, S. Messaoudi, "Electrochemical nickel-​catalyzed Migita cross-​coupling of 1-​thiosugars with aryl, alkenyl and alkynyl bromides", Chem. Chomm. 2020, 56, 4464-4467. link

94. B. Letribot, W. Redjdal, B. Benmerad, F. Le Bideau, M. Alami, S. Messaoudi, "Synthesis of N-​Glycosyl-​2-​oxindoles by Pd-​Catalyzed N-​Arylation of 1-​Amidosugars", Org. Lett. 2020, 22, 4201-4206. link

93. N. Ibrahim, P. Bonnet, J. D. Brion, J. F. Peyrat, J. Bignon, H. Levaique, B. Josselin, T. Robert, P. Colas, S. Bach, S. Messaoudi, M. Alami, A. Hamze, "Identification of a new series of flavopiridol-​like structures as kinase inhibitors with high cytotoxic potency", Eur. J. Med. Chem. 2020, 199, 112355. link

92. J. Ghouilem, R. Franco, P. Retailleau, M. Alami, V. Gandon, S. Messaoudi, "Regio- and diastereoselective Pd-​catalyzed synthesis of C2-​aryl glycosides", Chem. Chomm. 2020, 56, 7175-7178. link

91. M. Hassine, H. Ben Jannet, N. Ghermani, M. Alami, S. Messaoudi, "Synthesis of N-​(Hetero)​arylconvolvine Derivatives through a Palladium-​Catalyzed Buchwald-​Hartwig Cross-​Coupling", Synthesis 2020, 52, 450-458. link

90. N. Bennai, A. Chabrier, M. Fatthalla, C. Tran, E. Yen-Pon, M. Belkadi, M. Alami, L. Grimaud, S. Messaoudi, "Reversing Reactivity : Stereoselective Desulfurative β-O-Glycosylation of Anomeric Thiosugars with Carboxylic Acids Under Copper or Cobalt Catalysis", J. Org. Chem. 2020, ,85, 8893-8909. link

89. Messaoudi, S. "Les thiosucres : réactivités et applications", L’actualité chimique 2020. link

88. Zhao, G. ; Zhu, M. ; Alami, M. ; and Messaoudi, S.* "Synthesis of 2,3-Substituted β-N-Glycosyl Indoles through C–H Activation/Annulation Process under Rh(III)-Catalysis", Org. Lett. 2020, , 22, 57-61.
link

2019

87. Verdelet, T. ; Benmahdjoub, S. ; Benmerad, B. ; Alami, M. ; and Messaoudi, S.* "Copper-catalyzed anomeric O-arylation of carbohydrate derivatives at room temperature", J. Org. Chem. 2019, 84, 9226-9238.
link

86. Zhu, M. ; Dagousset, G. ; Alami, M. ; Magnier, E. ; and Messaoudi, S.* "Ni/Photoredox-Dual-Catalyzed Functionalization of 1-Thiosugars", Org. Lett. 2019, , 21, 5132-5137. In memory of Professor Françis COUTY
link

85. Mathieu, C. ; Messaoudi, S. ; Fattal, E. ; Vergnaud-Gauduchon,J. * "Cancer drug resistance : rationale for drug delivery systems and targeted inhibition of HSP90 family proteins", Cancer Drug Resist. 2019, accepted.

84. Montoir, D. ; Amoura, M. ; Ababsa, Z.E.-A. ; Vishwanath, T. M. ; Yen-Pon, E. ; Robert, V. ; Beltramo, M. ; Piller, V. ; Alami, M. ; Aucagne, A.* and Messaoudi, S.* "Synthesis of Aryl-Thioglycopeptides Through Chemoselective Pd-Mediated Conjugation", Chem.Sci. 2018, 9, 8753-8759, link

83. Ibrahim, N. ; Alami, M. ; Messaoudi, S.* "Recent Advances in Transition Metal‐Catalyzed Functionalization of 1‐Thiosugars", Asian. J. Org. Chem. 2018, 7, 2026-2038 ].
link

82. Probst, N., Grelier, G., Dahaoui, S., Alami, M. ; Gandon,* V., Messaoudi, S.* "Palladium(II)-Catalyzed Diastereoselective 2,3-trans C(sp3)-H Arylation of Glycosides", ACS. Catal. 2018, [DOI : 10.1021/acscatal.8b01617].
link

81. S. Benmahdjoub, N. Ibrahim, B. Benmerad, M. Alami, S. Messaoudi* "One-Pot Assembly of Unsymmetrical Biaryl Thioglycosides through Chemoselective Palladium-Catalyzed Three-Component Tandem Reaction", Org. Lett. 2018, 20, 4067–4071.
link

80. F. Sauvage, E. Fattal ; W. Alshaer ; S. Denis ; E. Brotin ; C. Denoyelle ; C. Blanc-Fournier ; B. Toussaint ; S. Messaoudi ; M. Alami ; G. Barratt and J. Vergnaud* " Antitumor activity of nanoliposomes encapsulating the novobiocin analogue 6BrCaQ in a triple-negative breast cancer model in mice", Cancer Lett. 2018, 432, 103-111.

79. F. Malard, N. Assir, M. Alami, S. Messaoudi, E. Lescop,* T. Ha-Duong* " Conformational Ensemble and Biological Role of the TCTP Intrinsically Disordered Region : Influence of Calcium and Phosphorylation", J. Mol. Bio 2018, 430, 1621-1639. link

78. K. H. Vardhan Reddy, E. Yen-Pon, S. Cohen-Kaminsky, S. Messaoudi*, M. Alami* " Convergent strategy to dizocilpine MK-801 and derivatives", J. Org. Chem 2018, 83, 4264-4269. 2018, 430, 1621-1639. link

77. Redjdal, W. ; Ibrahim, N. ; Alami, M. ; Messaoudi, S.* " Convergent Synthesis of N,S-bis Glycosylquinolin-2-ones via a Pd-G3-XantPhos Precatalyst Catalysis", Molecules 2018, 23,519. Invited contribution for Special Issue Glycomimetics : Design, Synthesis and Therapeutic Applications
link

76. Probst, N. ; Lartia, R. ; Théry, O. ; Alami, M. ; Defrancq, E. ; Messaoudi, S.* " Efficient Buchwald–Hartwig–Migita Cross-Coupling for DNA Thioglycoconjugation", Chem. Eur. J 2018, 24, 1795-1800. link

2017

75. AL-Shuaeeb, R.-A.-A. ; Dejean. C. ; Alami, M. ; Messaoudi, S.* "Controllable Activation of Pd-G3 Palladacycle Precatalyst in the Presence of Thiosugars : Rapid Access to 1-Aminobiphenyl Thioglycoside Atropoisomers at Room Temperature", Chem. Asian. J 2017, xx, DOI : 10.1002/asia.201701415. link

74. Probst, N., Grelier, G., Ghermani, N., Gandon, V., Alami, M. ; Messaoudi, S.* "Intramolecular Pd-Catalyzed Anomeric C(sp3)–H Activation of Glycosyl Carboxamides", Org. Lett. 2017, 19, 5038–5041. link

73. AL-Shuaeeb, R.-A.-A. ; Montoir, D. ; Alami, M. ; Messaoudi, S.* "Synthesis of (1 → 2)-S-Linked Saccharides and S-Linked Glycoconjugates via a Palladium-G3-XantPhos Precatalyst Catalysis", J. Org. Chem. 2017, 82, 6720–6728. link

72. Luong,T. T. H. ; Touchet, S. ; Alami, M. ; Messaoudi, S.* "Selective Palladium-Catalyzed Domino Heck/Buchwald-Hartwig Arylations of N-Glycosylcinnamamides : An Efficient Route to 4-Aryl N-Glycosyl Quinolin-2-ones", Adv. Synth. Catal. 2017, 359, 1320–1330. link

71. Galvani, G. ; Reddy, K. H. V. ; Beauvineau, C. ; Ghermani, N. ; Mahuteau-Betzer, F. ; Alami, M.* ; Messaoudi, S.* "Conversion of 3-bromo-2H-coumarins to 3-(benzofuran-2-yl)-2H-coumarins under palladium catalysis : Synthesis and Photophysical Properties Study", Org. Lett. 2017, 19, 910–913. link

70. F. Sauvage, S. Messaoudi, E. Fattal, G. Barratt, J. Vergnaud-Gauduchon* "Heat shock proteins and cancer : how can nanomedicine be harnessed ?", J. Control. Release, 2017, 248, 133-143.
link

2016

69. E. Defrancq, S. Messaoudi* "Pd-mediated labeling of nucleic acids", ChemBioChem, 2017, 18, 426 –431. link

68. A. Chabrier, A. Bruneau, S. Benmahdjoub, B. Benmerad, S. Belaid , J.-D. Brion, M. Alami, and S. Messaoudi* "Stereoretentive copper catalyzed directed thioglycosylation of C(sp2)-H bonds of benzamides ", Chem. Eur. J, 2016, 22, 15006-15010 (VIP). link

67. R. Ahmed Atto Al-Shuaeeb, S. Kolodych, O. Koniev, S. Delacroix, S. Erb, S. Nicolaÿ, J-C. Cintrat, J.-D. Brion, S. Cianférani, M. Alami, A. Wagner and S. Messaoudi* "Palladium Catalyzed Chemoselective and Biocompatible Functionalization of Cysteine-Containing Molecules at Room Temperature", Chem. Eur. J, 2016, 22, 11365 –11370 . link

66. Luong, T. T. H. ; Brion, J.-B. ; Lescop, E. ; Alami, M.* ; Messaoudi, S.* "Intramolecular Pd-Catalyzed Arylation of 1-Amidosugars : A New Route to N-Glycosyl Quinolin-2-ones", Org. Lett. 2016, 18, 2126–2129 link

65. F. Sauvage, S. Franzè, A. Bruneau, M. Alami, S. Denis, V. Nicolas, S. Lesieur, F.-X. Legrand, G. Barratt, S. Messaoudi, Vergnaud-Gauduchon J. “Formulation and in vitro efficacy of liposomes containing the hsp90 inhibitor 6BrCaQ in prostate cancer cells”. Int. J. Pharmaceut. 2016, 499, 101– 109. link

64. K. H. Vardhan Reddy, J.-D. Brion, S. Messaoudi*, M. Alami*. "Synthesis of Biheterocycles Based on Quinolinone, Chromone, and Coumarin Scaffolds by Palladium-Catalyzed Decarboxylative Couplings". J. Org. Chem. 2016, 81, 424– 432.
link

2015

63. Al-Shuaeeb, R. A. A. ; Galvani, G. ; Bernadat, G. ; Alami, M.* ; Messaoudi, S*. "Diversty-oriented synthesis of fused thioglycosyl benzo[e][1,4]oxathiepin-5-ones and benzo[f][1,4]thiazepin-5(2H)-ones by a sequences of palladium-catalyzed glycosyl thiol arylation and deprotection-lactonization reactions". Org. Biomol. Chem. . 2015. 13, 10904– 10916.
link

62. Soussi, M. A. ; Provot, O. ; Bernadat, G. ; Bignon, J. ; Lenoir, C. ; Dubois, J. ; Brion, J. D. ; Messaoudi, S* ; Alami A*. "IsoCombretaQuinazolines : Potent Cytotoxic Agents with Antitubulin Activity". ChemMedChem. 2015. 10, 1392– 1402.
link

61. Bruneau, A. ; Roche, M. ; Hamze, A. ; Brion, J.-D. ; Alami, M*. ; Messaoudi, S.* "Stereoretentive Palladium-Catalyzed Arylation, Alkenylation and Alkynylation of 1-Thiosugars and Thiols Using Aminobiphenyl Palladacycle Precatalyst at Room Temperature", Chem. Eur. J, 2015, 21, 8375 – 8379. link

60. Bruneau, A. ; Roche, M. ; Alami, M*. ; Messaoudi, S.* "2-Aminobiphenyl Palladacycles : the “Most Powerful” Precatalysts in C−C and C−heteroatom Cross-Couplings", ACS Catal. 2015, 5, 1386–1396. link

59. Luong, T. T. H. ; Brion, J.-B. ; Alami, M.* ; Messaoudi, S.* "Synthesis of Fused 1-aminoindole Polycycles by a Sequence of Palladium-Catalyzed N-H and C(sp2)-H Arylations", J. Org. Chem. 2015, 80, 751-761. link

58. Luong, T. T. H. ; Brachet, E. ; Brion, J.-B. ; Messaoudi, S.*, Alami, M.* ; "Palladium-Catalyzed Coupling of N-Aminoazoles with 3-Haloquinolin-2(1H)-ones, -Coumarins, -Quinoxalin-2(1H)-ones and -Chromenes", Eur. J. Org. Chem.. 2015, 1771–1780 . link

2014

57. Alami, M. ; Hamze, A. ; Messaoudi, S. Coupling reactions between sp Carbon Centers. In Comprehensive Organic Synthesis, Molander, G. ; Knochel, P., 2nd Eds. ; Pergamon Press : Oxoford, UK, 2014, UK, 3, 528–579
(book chapter on invitation)
link

56. Aziz, J. ; Messaoudi, S.* ; Alami, M.* ; Hamze, A. "Sulfinate Derivatives : Dual and Versatile Partners in Organic Synthesis" Org. Biomol. Chom.. 2014. 12, 9743-9759 . link

55. Carrër, A ; Brion, J.-B. ; Alami, M.* ; Messaoudi, S.* "Assisted tandem Pd(II)/Pd(0)-catalyzed C- and N-arylations of quinoxalin-2(1H)-ones in water", Adv. Synth. Catal. 2014, 356, 3821 – 3830. link

54. Bruneau, A. ; Brion, J.-B. ; Messaoudi, S.* ; Alami, M.* "A General Pd/Cu-Catalyzed C-H Heteroarylation of 3-Bromoquinolin-2(1H)-ones" Org. Biomol. Chom.. 2014. 12, 8533 - 8541.
link

53. D. Audisio, D-. Methy-Gonnot, C. Radanyi, J.-M. Renoir,
S. Denis, F. Sauvage, J. Vergnaud-Gauduchon, J.-D. Brion, S. Messaoudi,* M. Alami* "Synthesis and antiproliferative activity of novobiocin analogues as potential hsp90 inhibitors", Eur. J. Med. Chem.. 2014, 83, 498–507.
link

52. M. A. Soussi, O. Provot, G. Bernadat, J. Bignon, J. Wdzieczak-Bakala, D. Desravines, J. Dubois, J.-D. Brion, S. Messaoudi,* M. Alami* "Discovery of Azaisoerianin Derivatives as Potential Antitumors Agents", Eur. J. Med. Chem.. 2014, 78, 178–189.
link

2013

51. Carrër, A ; Brion, J.-B. ; Messaoudi, S.* ; Alami, M.* "Palladium(II)-Catalyzed Oxidative Arylation of Quinoxalin-2(1H)-ones with Arylboronic acids", Org. Lett.. 2013, 15, 5606–5609.
link

50. Brachet. E ; Brion, J.-B. ; Alami, M.* ; Messaoudi, S.* "Nickel Catalyzed Arylation, Alkenylation and Alkynylation of Unprotected Thioglycosides at Room Temperature" Chem. Eur. J. 2013, 2013, 19, 15276 – 15280. link

49. Bruneau, A. ; Brion, J.-B. ; Alami, M.* ; Messaoudi, S.* "Stereoselective copper-catalyzed Chan-Lam-Evans N-arylation of glucosamines with arylboronic acids at room temperature" Chem. Commun. 2013. 49, 8359-8361. Link

48. Brachet. E ; Brion, J.-B. ; Alami, M.* ; Messaoudi, S.* "Stereoselective Palladium-Catalyzed Alkenylation and Alkynylation of Thioglycosides" Adv. Synth. Catal. 2013, 355, 2627 – 2636. link

47. Carrër, A ; Brion, J.-B. ; Messaoudi, S.* ; Alami, M.* "Synthesis of 3,4-Disubstituted Quinolin-2-(1H)-ones via Palladium Catalyzed Decarboxylative Arylation Reactions", Adv. Synth. Catal. 2013, 355, 2044 – 2054. link.

46. Brachet. E ; J. F. Peyrat, Brion, J.-B. ; Messaoudi, S.* ; Alami, M.* "Palladium-Catalyzed Coupling of 3-Chloroquinoxalinones with Various Nitrogen-Containing Nucleophiles". Org. Biomol. Chem. 2013, 11, 3808-3816. Selected for cover picture link

45. Brachet. E ; Brion, J.-B. ; Messaoudi, S.* ; Alami, M.* "Palladium-Catalyzed Cross-Coupling Reaction of Thioglycosides with (Hetero)aryl Halides", Adv. Synth. Catal. 2013, 355, 477–490. Link

44. Messaoudi, S.* ; Gabillet, M. ; Brion, J.-B. ; Alami, M.* "An efficient synthesis of 3-triazolyl-2(1H)-quinolones by CuTC-catalyzed azide-alkyne cycloaddition reaction", Appl. Organomet. Chem. 2013, 27, 155–158. Link.

43. Messaoudi, S.* ; Peyrat, J.-F. ; Brion, J.-D. ; Alami, M. Recent Advances in Hsp90 Inhibitors as Antitumor Agents. In Advances in Anti-Cancer Agents in Medicinal Chemistry Ed. M. Prudhomme, Bentham Sciences Publishers 2013, 1, 107-183 (book chapter on invitation)

link

Advances in Anticancer Agents in Medicinal Chemistry is an exciting eBook series comprising a selection of updated articles previously published in the peer-reviewed journal Anti-Cancer Agents in Medicinal Chemistry. The first volume gathers reviews of many classes of drugs of contemporary interest for cancer therapy and is devoted to small molecules inhibitors of various proteins involved in cancer development such as Casein kinase 2 (CK2), Protein kinase B (PKB), mTOR, Hsp90, P-glycoprotein (P-gp), Kinesin spindle protein (KSP), Cyclooxygenase 2 (COX-2), Histone deacetylase enzymes (HDACs) and Topoisomerase I.

2012

42. Giessrigl, B. ; Krieger, S. ; Rosner, M. ; Huttary, N. ; Saiko, P. ; Alami, M. ; Messaoudi, S. ; Peyrat, J.-F. ; Maciuk, A. ; Gollinger, M. ; Kopf, S. ; Kazlauskas, E. ; Mazal, P. ; Szekeres, T. ; Hengstschla¨ger, M. ; Matulis, D. ; Ja¨ger, W. ; Krupitza, G.* “Hsp90 stabilizes Cdc25A and counteracts heat shock-mediated Cdc25A degradation and cell-cycle attenuation in pancreatic carcinoma cells”
Hum. Mol. Genet. 2012, 21, 4615-4627

Link : http://hmg.oxfordjournals.org/content/21/21/4615.long

41. Brachet. E ; Messaoudi, S.* ; Peyrat, J.-F. ; Brion, J.-B. ; Alami, M.* "Palladium-Catalyzed Cross-Coupling of 1-Aminoazoles with Aryl Chlorides : Application to the Synthesis of Unsymmetrical N,N′-Diaryl-1-Aminoindoles", Adv. Synth. Catal. 2012, 354, 2829 – 2839

Link : http://onlinelibrary.wiley.com/doi/10.1002/adsc.201200440/abstract

40. Sahnoun, S. ; Messaoudi, S.* ; Peyrat, J.-F. ; Brion, J.-B. ; Alami, M.* "Cs2CO3 in pyrrolidinone promoted hydration of functionalized (hetero)aryl nitriles under metal-free conditions", Tetrahedron Lett. 2012. 53, 2860-2863.
http://www.sciencedirect.com/science/article/pii/S0040403912005448

39. Audisio, D. ; Messaoudi, S.* ; Cojean, S.* ; Peyrat, J.-F. ; Brion, J.-B. ; Bories, C. ; Huteau, F. ; Loiseau, M.-P. ; Alami, M. "Synthesis and antikinetoplastid activities of 3-substituted quinolinones derivatives" Eur. J. Med. Chem. 2012, 52, 44-50.
http://www.sciencedirect.com/science/article/pii/S022352341200147X

38. Messaoudi, S.* ; Brion, J.-B. ; Alami, M.* "Palladium-Catalyzed Decarboxylative Coupling of Quinolinone-3-Carboxylic Acids and Related Heterocyclic Carboxylic Acids with (Hetero)aryl Halides". Org. Lett., 2012, 14 , 1496–1499. http://pubs.acs.org/doi/abs/10.1021/ol300235k

2011

37. Messaoudi, S. ; Peyrat, J.-F.* ; Brion, J.-B. ; Alami, M.* “Heat-shock protein 90 inhibitors as antitumor agents : a survey of the literature from 2005 to 2010Expert. Op. Th. Pat. 2011, 21, 1501–1542.

link : http://informahealthcare.com/toc/etp/21/10.

36. Soussi, M. A. ; Aprile,S. Messaoudi, S. ; Provot, O. ; Del Grosso,E. ; Bignon, J. ; Dubois, J. ; Brion, J.-B. ; Grosa, G. ;* Alami, M.* “Metabolic Fate of isoCombretastatin A-4 in Human Liver Microsomes : Identification, Synthesis and Biological Evaluation of MetabolitesChemMedChem. 2011, 6, 1781–1788
link : http://onlinelibrary.wiley.com/doi/10.1002/cmdc.201100193/abstract

35. Audisio, D. ; Messaoudi, S.* ; Peyrat, J.-F. ; Brion, J.-B. ; Alami, M.* "A General Copper Powder-Catalyzed Ullmann-Type Reaction of 3-Halo-4(1H)-quinolones With Various Nitrogen-Containing Nucleophiles" J. Org. Chem. 2011, 76, 4995–5005

34. Soussi, M. A. ; Audisio, D. ; Messaoudi, S. ;* Provot, O. ; Brion, J.-B. ; Alami, M.* “Palladium-Catalyzed Coupling of 3-Halo-Substituted Coumarins, Chromenes, and Quinolones with Various Nitrogen-Containing Nucleophiles” Eur. J. Org. Chem. 2011, 5077-5088

33. Messaoudi, S.* ; Brion, J.-B. ; Alami, M.* “Copper-Catalyzed Direct Amination of Halo(hetero)arenes With Sodium Azide As The Amino SourceMini Rev. Org. Chem. 2011, 8, 448-454.

link : http://www.benthamscience.com/contents-JCode-MROC-Vol-00000008-Iss-00000004.htm#13170945

32. Sahnoun, S. ; Messaoudi, S.* ; Brion, J.-B. ; Alami, M.* “Pd-Catalyzed Direct benzylation of XanthinesChemCatChem. 2011, 3, 893-897.

31. Messaoudi, S.* ; Brion, J.-D. Alami, M.* "Palladium-catalyzed selective N-(hetero)arylation or N,N’-di(hetero)arylation of 1-aminoindoles" Tetrahedron. Lett. 2011, 52, 2687-2691

30. Audisio, D. ; Messaoudi, S. ; Cegielkowski, L. ; Peyrat, J.-F. ; Brion, J.-D. ; Methy-Gonnot, D. ; Radanyi, C. ; Renoir, J.-M. ; and Alami, M.* ChemMedChem. 2011, 6, 804-816.
link : http://onlinelibrary.wiley.com/doi/10.1002/cmdc.201000489/abstract

29. Messaoudi, S. ; Hamze, A. ; Provot, O. ; Tréguier, B. ; Rodrigo De Losada, J. R. ; Bignon, J. ; Liu, J.-M. ; Wdzieczak-Bakala, J. ; Thoret, S. ; Dubois, J. ; Brion, J.-D. ; Alami, M.* "Discovery of Novel isoErianin Analogues as Promising Anticancer Agents" ChemMedChem. 2011. 6, 488-497

2010

28. Sahnoun, S. ; Messaoudi, S. ; Brion, J.-B. ; Alami, M.* “Pd/Cu-Catalyzed Direct Alkenylation of Azole Heterocycles with Alkenyl Halides” Eur. J. Org. Chem. 2010, 6097-6102.

27. Messaoudi, S. ;* Brion, J.-B. ; Alami, M.* “Transition Metal-Catalysed Direct Alkenylation, Alkynylation, Benzylation and alkylation of (Hetero)arene C–H Bonds” Eur. J. Org. Chem. 2010, 6495-6516. Hottest article in the field of catalysis

Most Accessed 12/2011–09/2012

Most Accessed 12/2010–11/2011

26. Peyrat, J.-F. ; Messaoudi, S*. ; Brion, J.-B. ; Alami, M.* “Inhibitors of the Heat Shock Protein 90 : From Cancer Clinical Trials to Neurodegenerative Diseases”. (Invited review)“Atlas Genet Cytogenet Oncol Haematol. 15, 89-105 2010, URL : http://AtlasGeneticsOncology.org/De...

25. Messaoudi, S*. ; Brion, J.-D. ; Alami, M.* “An Expeditious Copper-Catalyzed Access to 3-Amino-quinolinones, 3-Aminocoumarins and Anilines using Sodium Azide” Adv. Synth. Catal. 2010, 352, 1677-1687.

24. Audisio, D.* ; Messaoudi, S. ; Ijjaali, I. ; Dubus, E. ; Petitet, F. ; Peyrat, J.-F. ; Brion, J.-B. ; Alami, M.* “Assessing the Chemical Diversity of an Hsp90 Database” Eur. J. Med. Chem. 2010, 45, 2000-2009

Cover Picture

23. Audisio, D. ; Messaoudi, S*. ; Brion, J.-B. ; Alami, M.* “A Straighfort Synthesis of Functionalized 3-Bromocoumarins via a One Pot Multi-Compenent Reaction” Eur. J. Org. Chem. 2010, 1046-1051.

2009

22. Alami, M. ; Messaoudi, S. ; Hamze, A. ; Provot, O. ; Brion, J.-D ; Bignon, J. ; Bakala-Wdzieczak, J. ; Liu, Jian-Miao."Dihydro-Iso-CA-4 and Analogues : Potent Cytotoxics, Inhibitors of Tubulin Polymerization" Brevet-CNRS-UPS N° FR 08/53694 ; étendu a l’international PCT N° EP2009/056885 du 4 juin 2009 (WO2008122620)

21. Hamze, A. ; Giraud, A. ; Messaoudi, S. ; Provot, O. ; Peyrat, J.-F. ; Liu, J.-M. ; Bignon, J. ; Bakala- Wdzieczak, J. ; Thoret, S. ; Dubois, J. ; Brion, J.-D. and Alami, M.* “Isocombretastatins A versus Combretatstatins A : The forgotten iso-CA-4 Isomer as a Highly Promissing Cytotoxic and Antitubilin Agent” ChemMedChem 2009, 4, 1912-1924

20. Sahnoun, S. ; Messaoudi, S. ; Brion, J.-B. ; Alami, M.* “A Site Selective C-H Arylation of Free-(NH2) Adenines with Aryl Chlorides : Application to the Synthesis of 6,8-Disubstituted Adenines” Org. Biomol. Chem. 2009, 7, 4271-4278

19. Messaoudi, S. ; Tréguier, B. ; Hamze, A. ; Provot, O. ; Peyrat, J.-F. ; Liu, J.-M. ; Bignon, J. ; Bakala- Wdzieczak, J. ; Thoret, S. ; Dubois, J. ; Brion, J.-D. and Alami, M.* “Isocombretastatins A versus Combretatstatins A : The forgotten iso-CA-4 Isomer as a Highly Promissing Cytotoxic and Antitubilin Agent” J. Med. Chem. 2009, 52, 4538–4542

18. Radanyi, C. ; Le Bras, G. ; Bouclier, C., Messaoudi, S., Peyrat, J.-F. ; Brion, J.-D. ; Alami, M. ; Renoir, J.-M. Radanyi, C. ; « Tosylcyclonivobiocic Acids Promote Cleavage Of The Hsp90-Associated Cochaperone p23 » Biochem and Biophys. Res. Comm. 2009, 379, 514-518.

17. Radanyi, C. ; Le Bras, G. ; Marsaud, V. ; Messaoudi, S. ; Peyrat, J.-F. ; Brion, J.-B. ; Alami, M and Renoir, J.-M. “Antiproliferative and apoptotic activities of tosylcyclonovobiocic acids as potents hsp90 inhibitors in humain cancer cells”. Cancer Lett., 2009, 274, 88-94.

2008

17. Sahnoun, S. ; Messaoudi, S. ; Peyrat, J.-F. ; Brion, J.-B. ; Alami, M. “Microwave Assisted Pd(OH)2–Catalyzed Direct C8 Arylation of Free-(NH2) –Adenines” Tetrahedron Lett. 2008, 49, 7279-7283 Highlighted in Org. Chem. Highlights, November 2008

16. Messaoudi, S*. ; Peyrat, J.-F. ; Brion, J.-B. ; Alami, M. “Recent Advances in Hsp90 Inhibitors as Antitumors Agents”. (Invited review) Anti-cancer Agents in Med. Chem. 2008, 8, 761-782. Highlighted as “Most Accessed Articles”

15. Hénon, H. ; Conchon, E. ; Hugon, B. ; Messaoudi, S. ; Golsteyn, R.-M. ; Prudhomme, M. “Pyrrolocarbazoles as Checkpoint 1 Kinase Inhibitors”. Anti-cancer Agents in Med. Chem. 2008, 8, 577-597.

14. Le Bras, G. ; Hamze, A. ; Messaoudi, S. ; Provot, O. ; Le Calvez, P.-B. ; Brion, J.-B. ; Alami, M. “Synthesis of isocoumarin via PTSA-catalyzed annulation of diarylalkynes”. Synthesis, 2008, 10, 1607-1611

13. Radanyi, C. ; Le Bras, G. ; Messaoudi, S. ; Bouclier, C. ; Peyrat, J.-F. ; Brion, J.-B. ; Marsaud, V. ; Renoir, J.-M. ; and Alami, M. “Synthesis and biological activity of simplified denoviose coumarins related to novobiocin as potent inhibitors of heat shock protein 90 (hsp90)”. Bioorg. Med. Chem. Lett., 2008, 18, 2495-2498.

12. Alami, M. ; Brion, J.-D ; Provot, O. ; Peyrat, J.-F. ; Messaoudi, S. ; Hamze, A. ; Giraud, A. ; Bignon, J. ; Bakala- Wdzieczak, J. ; Liu, Jian-Miao. "IsoCA4 and Analogues and Thereof as Potent Cytotoxics agents Inhibiting Tubulin Polymerization" Brevet-CNRS-UPS N° 0754280 ; dépose le 04 avril 2007 ; étendu a l’international PCT N° EP2008/054118 du 4 avril 2008 (WO2008122620).

2007

11. Audisio, D. ; Messaoudi, S. ; Peyrat, J.-F. ; Brion, J.-D. ; Alami, A.“ A Convenient and Expeditious Synthesis of 3-(N-Substituted) Aminocoumarins via Palladium-Catalyzed Buchwald-Hartwig Coupling Reaction”. Tetrahedron Lett., 2007, 48, 6928-6932.

10. Olivi, N. ; Messaoudi, S. ; Russo, O. ; Hamze, A. ; Peyrat, J.-F. ; Brion, J.-D. ; Sicsic, S. ; Berque-Bestel, I. ; Alami, A. “Tandem Williamson-Sonogashira reaction : new three Component Nitrogen propargelation / alkynylation of organic halides” Tetrahedron, 2007, 63, 10671-10683

9. Messaoudi, S. ; Audisio, D. ; Brion, J.-D. ; Alami, A.“Rapid Access to 3-(N-Substituted) Aminoquinolin-2(1H)-ones using Palladium-Catalyzed C-N bond Coupling Reaction”. Tetrahedron, 2007, 63, 10202-10210.

8. Hénon, H. ; Messaoudi, S. ; Anizon, A. ; Aboab, B. ; Kucharczyk, N. ; Léonce, S. ; Golsteyn, M. G. ; Pfeiffer, B. ; Prudhomme, M. "Bis-imide granulatimide analogues as potent Checkpoint 1 kinase inhibitors". Eur. J. Pharmacology, 2007, 554, 106–112.

2006

7. Messaoudi, S. ; Anizon, F. ; Peixoto, P. ; David-Cordonnier, M-H. ; Golsteyn, R. ; Léonce, S. ; Pfeiffer, B. ; Prudhomme, M. ; "Synthesis and biological activities of 7-aza rebeccamycin analogues bearing the sugar moiety on the nitrogen of the pyridine ring". Bioorg. Med. Chem., 2006, 14, 7551–7562

6. M, Sassatelli. ; F. Bouchikki. ; S, Messaoudi. ; F, Anizon. ; E. Debitonb, C. Barthomeufb, M, Prudhomme. ; P, Moreau. "Synthesis and antiproliferative activities of diversely substitued glycosyl-isoindego derivattives". Eur. J. Med. Chem. ; 2006, 41,88–100.

2005

5. Henon, H. ; Messaoudi, S. ; Hugon, B. ; Anizon, F. ; Pfeiffer, B. ; Prudhomme, M. ; "Synthesis of granulatimide bis-imide analogues" Tetrahedron, 2005, 61, 5599-5614.

4. Messaoudi, S. ; Anizon, F. ; Léonce, S. ; Pierré, A. ; Pfeiffer, B. ; rudhomme, M. ; "Synthesis and in vitro cytotoxicities of 7-aza rebeccamycin analogues bearing various substituents on the sugar moiety, on the imide nitrogen and on the carbazole framework". Eur. J. med.Chem , 2005, 40, 961-971

3. Messaoudi, S. ; Anizon, F. ; Léonce, S. ; Pierré, A. ; Pfeiffer, B. ; Prudhomme, M. ; "Synthesis and in vitro cytotoxicities of bridged aza-rebeccamycin derivatives". Tetrahedron, 2005, 61, 7304-7316

2004

2. Messaoudi, S. ; Anizon, F. ; Pfeiffer, B. ; Golsteyn, R. ; Prudhomme, M. ; "Synthesis of a staurosporine analogue possessing a 7-azaindole unit instead of an indole moiety". Tetrahedron lett. ; 2004, 45, 4643-4647

1. Messaoudi, S. ; Sancelme, M. ; Polard-Housset, V. ; Aboab, B. ; Moreau, P. ; Prudhomme M. ; "Synthesis and biological evaluation of oxindoles and benzimidazolinones derevatives" Eur. J. Med.Chem, 2004, 39, 453-458.


Chargé de Recherche CNRS (CR1)

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Samir Messaoudi est lauréat du "Prix d’encouragement à la recherche en chimie thérapeutique"

Samir Messaoudi (Chargé de Recherche CNRS) est lauréat du "Prix d’encouragement à la recherche en chimie thérapeutique" 2012 décerné par les laboratoires SERVIER en partenariat avec la Société de Chimie Thérapeutique SCT.

Ce prix a été remis à la fin de la conférence qui a été donnée par le bénéficiaire lors de la journée d’automne de la SCT qui a eu lieu en Novembre 2013.

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