Breakthroughs in Medicinal Chemistry: New Targets and Mechanisms, New Drugs, New Hopes-​4

Mangoni A. A; Guillou, C.; Vanden Eynde, J-J.; Hulme, C; Jampilek, J.; Li, W.; Prokai-Tatrai, K.; Rautio, J.; Collina, S.; Tuccinardi, T.; Sousa, M.E.; Sabatier, J-M; Galdiero, S.; Karaman, R.;  Kokotos, G.; Torri, G.; Luque, F-J. Vasconcelos, M-H.; Hadjipavlou- Litina, D.; Siciliano, C.; Gutschow, M.; Ragno, R.; Gomes, P.A.C; Agrofoglio, L-A.;   Munoz-Torrero, D.

Molecules 2019, 24, 130

Mild Rhodium(III)-Catalyzed Intramolecular Annulation of Benzamides with Allylic Alcohols to Access  Azepinone Derivatives

Peneau, A.; Tricart, Q. ; Guillou, C.; Chabaud, L.

Chem. Comm. 2018, 54, 5891-5894

Rhodium(III)-Catalyzed Synthesis of Spiropiperidine Derivatives via C-H Activation

Peneau, A.; Retailleau, P.; Guillou, C.; Chabaud, L.

J. Org. Chem.2018, 83, 2324-2340

Breakthroughs in Medicinal Chemistry: New Targets and Mechanisms, New Drugs, New Hopes-3

Mangoni, A. A.; Tuccinardi, T.; Collina, S.; Vanden, Eynde, J-J.; Munoz-Torrero, D.;* Karaman, R.;        Karaman, R.; Siciliano, C.; de Sousa Maria, E.; Prokai-Tatrai, K. ; Rautio, J. ; Guillou, C. ; Gütschow,          M. ; Galdiero , S. ; Liu, H. ; Agrofoglio, L.A. ; Sabatier, J.M. ; Hulme, C. ; Kokotos, G. ; You, Q. ; Gomes, P.A.C.

Molecules 2018, 23 , 1596

Recent Advances in [Cp*M(III)] (M = Co, Rh, Ir)-Catalyzed Intramolecular Annulation Through C–H Activation

Peneau, A.; Guillou, C.; Chabaud, L.

Eur. J. Org. Chem. 2018, 5777-5794

Breakthroughs in Medicinal Chemistry: New Targets and Mechanisms, New Drugs, New Hopes-2

Munoz-Torrero, D.; Mangoni, A.A.; Liu, H.; Hulme, C.; Rautio, J.; Karaman, R.; Karaman, R.; de Sousa Maria, E.; Prokai-Tatrai, K.; Sabatier, J.M.; Siciliano, C.; Luque, F.J.; Kokotos, G.; Ragno, R.; Collina, S.; Guillou, C.; Gutschow, M.; Agrofoglio, L.A.

Molecules 2018, 23, 65

Coupling fission and exit of RAB6 vesicles at Golgi hot spots through kinesin-myosin interactions

Miserey-Lenkei, S.; Bousquet, H.; Pylypenko, O.; Bardin, S.; Dimitrov, A.; Bressanelli, G.; Bonifay, R.; Fraisier, V.; Guillou, C.; Bougeret, C.; Houdusse, A.; Echard, A.; Goud, B.

Nat. Commun. 2017, 8, 1254

A direct label-free MALDI-TOF mass spectrometry based assay for the characterization of   inhibitors of protein lysine    methyltransferase

Guitot, K.; Drujon, T.; Burlina, F.; Sagan, S.; Beaupierre, S.; Pamlard, O.; Guillou, C.; Bolbach, G.; Sachon, E.; Guianvarc’h, D.

Anal. Bioanal. Chem. 2017, 409, 3767-3777

Breakthroughs in Medicinal Chemistry: New Targets and Mechanisms, New Drugs, New Hopes

Muñoz-Torrero, D.; Mangoni, A. A.; Guillou, C.; Collina, S.; Vanden Eynde, J.J.; Rautio, J.; Keserü, .M.; Hulme, C.; Chibale, K.; Luque, F.J.; Karaman, R.; Gutschow, M.; Hong Liu, H.; Ragno, R.

Molecules 2017, 22, 743

Holaphyllamine, a steroid, is able to induce defense responses in Arabidopsis thaliana and increases  resistance against bacterial infection

Abderrakib, Z.; Laggoun, F; Lehner, A.; Remy-Jouet, I.; Pamlard, O.; Beaupierre, S.; Leprince, J.; Latour, X.; Richard, V.; Guillou, C.; Lerouge, P.; Azeddine Driouich, A.; Mollet, J. C.

Planta, 2017,246, 1109 -1124

New MKLP-2 Inhibitors in the Paprotrain Series: Design, Synthesis and Biological Evaluation

Labriere, C. ; Talapatra, S. K., Thoret, S., Bougeret, C., Kozielski, F., Guillou, C.

Bioorg. Med. Chem. 2016, 24, 721-734

Further investigation of Paprotrain: Towards the conception of selective and multi-targeted CNS kinase inhibitors

Labriere, C.; Olivier Lozach, O.; Blairvacq, M.; Meijer, L.; Guillou, C.

Eur. J. Med. Chem. 2016, 124, 920-934

Rhodium(III)-Catalyzed Synthesis of Aryl Spirocycles by Aromatic C-H Activation/Intramolecular Heck-Type Reaction
Chabaud, L.; Raynal, Q.; Barre, E.; Guillou, C.
Adv. Synth. Catal., 2015, 357, 3880-3884

Hypervalent-Iodine-Mediated Synthesis of 1,2-Dispirodienones: Experimental and Theoretical Investigations
Hromjakova, T.; Retailleau, P.; Grimaud, L.; Gandon, V.; Chabaud, L.; Guillou, C.
Eur. J. Org. Chem., 2015, 7494-7503.

Iminosugars as a new class of cholinesterase inhibitors
Decroocq, C.; Stauffert, F.; Pamlard, O.; Oulaïdi, F.; Martin, O. R.; Guillou, C.; Compain, P.
Bioorg. Med. Chem. Lett., 2015, 25, 830-833.

Enantioselective Synthesis of Spiroimines by Asymmetric Decarboxylative Alkylation/Isomerization/[3+2]-Cycloaddition Reaction of Azidoalkenes
Rambla, M. ; Leslie Duroure, L. ; Chabaud, C. ; Guillou, C.
Eur. J. Org. Chem. 2014, 24, 7716-7720

Shogaol-huprine hybrids: dual antioxidant and anticholinesterase agents with β-amyloid and tau anti-aggregating properties
Pérez-Areales, F. J.; Di Pietro, O.; Espargaró, A.; Vallverdú-Queralt, A.; Galdeano, C.; Ilaria Ragusa, M.; Viayna, E.; Guillou, C.; Victòria Clos, M.; Pérez, B.; Sabaté, R.; Lamuela-Raventós, R. M.; Javier Luque, F.; Muñoz-Torrero, D.
Bioorg. Med. Chem. 2014, 22, 5298-5307

Synthesis of γ-butenolides and α,β-unsaturated γ-butyrolactams by addition of vinylogous nucleophiles to Michael acceptors Review on invitation.
Jusseau, X.; Chabaud, L.; Guillou, C.
Tetrahedron 2014, 70, 2595-2615

Hypervalent Iodine-Mediated Oxidative Cyclisation of p-Hydroxy Acetanilides to 1,2-Dispirodienones
Chabaud, L. ; Hromjakova, T. ; Matt Rambla, M. ; Retailleau, P. ; Guillou, C.
Chem. Comm. 2013, 49, 11542-11544

Catalytic Enantioselective Vinylogous Mukaiyama-Michael Addition of 2-Silyloxyfurans to Cyclic Unsaturated Oxo Esters: A Rapid Access to Optically Active γ-Butenolides.
Jusseau, X.; Retailleau, P.; Chabaud, L.; Guillou, C.
J. Org. Chem. 2013, 78, 2289-2300 Highlights : Synfacts 2013, 6, 645. Synfacts 2013, 7, 761.

Bioavailability of 13-desmethyl spirolide-C and improvement of Alzheimer disease markers in vivo observed by Proton magnetic resonance spectroscopy and immunoblotting analysis.
Alonso, E.; Otero, P.; Vale, C.; Alfonso, A.; Antelo, A.; Giménez-Llort, L.; Chabaud, L.; Guillou, C.; Botana, L. M.
Curr. Alzheimer Res. 2013, 10, 279-289

Studies on the Asymmetric Birch Reductive Alkylation to Access Spiroimines.
Jousseaume, T.; Retailleau, P.; Chabaud, L.; Guillou, C.
Tetrahedron Lett. 2012, 11, 1370-1372

6,6-Spiroimine Analogs of (–)-Gymnodimine A : Synthesis and Biological Evaluation on Nicotinic Acetylcholine Receptors.
Duroure, L.; Jousseaume, T.; Aráoz, R.; Barre, E.; Retailleau, P.; Chabaud, L.; Molgó,J.; Guillou, C.
Org. Biomol. Chem. 2011, 23, 8112-8118

Kinetic Study of Deuterium-labelled 4’-O-methylnorbelladine Rearrangement in Leucojum aestivum Shoot Cultures by Mass Spectroscopy. Influence of Precursor Feeding on Amaryllidaceae Alkaloid Accumulation.
El Tahchy, A.; Ptak, A.; Boisbrun, M.; Barre, E.; Guillou, C.; Dupire, F.; Chrétien, F.; Henry, M.; Chapleur, Y.; and Laurain-Mattar, D.
J. Nat. Prod. 2011, 74, 2356-2361

New Potent Acetylcholinesterase Inhibitors in the Tetracyclic Triterpene Series with inhibitory potency on β-amyloid aggregation.
Rouleau, J.; Iorga, B. ; Guillou, C.
Eur. J. Med. Chem. 2011, 46, 2193-2205

Effect of Sucrose and Growth Regulators on Acetylcholinesterase Inhibitory Activity of Alkaloids Accumulated in Amaryllidaceae Tissue Cultures.
El Tahchy, A.; Bordage,S.; Ptak, A.; Dupire, F.; Barre, E.; Guillou, C.; Henry, M.; Chapleur, Y.; Laurain-Mattar, D.
Plant Cell, Tissue and Organ Culture (PCTOC) 2011, 106, 381-390

Spiroimine toxins in complex with nicotinic acetylcholine receptors: structure and dynamics.
Araoz R., Chabaud L., Guillou C., Molgo J., Iorga B.
Biophys. J 2011, 100(3 suppl. 1, 347a

Molecular dynamics studies of acetylcholine binding protein with spiroimine toxins.
Araoz R., Chabaud L., Guillou C., Molgo J., Iorga B.
Advances and new technologies in Toxinology 2010, 109-114

Relocation of Aurora B and Survivin from Centromeres to the Central Spindle Impaired by a Kinesin-Specific MKLP-2 Inhibitor.
Tcherniuk, S.; Skoufias, D.A.; Labriere, C.; Rath, O.; Gueritte, F.; Guillou, C.; Kozielski, F.
Angew. Chem. Int. Ed. Engl. 2010, 49, 8228-8231

Catalytic Vinylogous Mukaiyama-Michael Reaction of Silyloxyfurans with Cyclic Enones.
Chabaud, L.; Jousseaume, T.; Retailleau, P.; Guillou, C.
Eur. J. Org. Chem. 2010, 5471-5481

Diastereoselective Total Synthesis of (±)-Codeine.
Varin, M.; Barré, E.; Iorga, B.; Guillou, C.
Chem-Eur. J. 2008, 14, 6606-6608 Highlight : Synfacts 2009, 2, 126.

Synthesis of deuterium-labelled (-)-galanthamine.
Rouleau, J.; Guillou, C.
J. Labelled Compd. Rad. 2008, 51, 236-238

Formal Total Syntheses of Aspidosperma Alkaloids via a Novel and General Synthetic Pathway Based on an Intramolecular Heck Cyclization.
Pereira, J.; Barlier, M.; Guillou, C.
Org. Lett. 2007, 9, 3101-3103

New Potent Acetylcholinesterase Inhibitors in the Tetracyclic Triterpene Series.
Sauvaître, T.; Barlier, M.; Herlem, D.; Gresh, N.; Chiaroni, A.; Guenard, D.; Guillou, C.
J. Med. Chem. 2007, 50, 5311-5323

A New Access to Dihydrotropones through Ring Expansion of Spirocyclohexadienones: Synthesis and Mechanism.
Varin, M.; Chiaroni, A.; Lallemand, J. Y.; Iorga, B.; Guillou, C.
J. Org. Chem. 2007, 27, 6421-6426

Structural features of neutral and protonated galanthamine : A crystallographic database and computational investigation
Kone, S. ; Galland, N. ; Graton, J. ; Illien, B. ; Laurence, C. ; Guillou, C. ; Le Questel, J.Y.
Chem. Phys. 2006, 328, 307-317.

Total syntheses of crinine and related alkaloids
Bru, C. ; Guillou, C.
Tetrahedron 2006, 62, 9043-9048.

An Unexpected Double-Bond Isomerization Catalyzed by Crabtree’s Iridium (I) Catalyst
Krel, M. ; Lallemand, J.Y. ; Guillou, C.
Synlett 2005, 13, 2043-2046.

Acetylcholine Nicotinic Receptors : Finding the Putative Binding Site of Allosteric Modulators Using the “Blind Docking” Approach
Iorga, B. ; Herlem, D. ; Barré, E. ; Guillou, C.
J. Mol. Model. 2005, 12, 366-372.

The complex of a bivalent derivative of galanthamine with Torpedo Acetylcholinesterase displays drastic deformation of the active-site gorge : Implications for structure-based drug design
H. M. Greenblatt, C. Guillou, D. Guenard, A. Argaman, S. Botti, B. Badet, C. Thal, I. Silman, J. L. Sussman
J .Am. Chem. Soc. 2004, 126, 15405-15411.

Synthesis and structure-activity relationships of open D-ring galanthamine analogues
D. Herlem, M.-T. Martin, C. Thal, C. Guillou
Bioorg. Med. Chem. Lett. 2003, 13, 2389-2391.

Concise total synthesis of (±)-maritidine
C. Bru, C. Thal, C. Guillou
Org. Lett. 2003, 5, 1845-1846.

Combined treatment with galanthaminium bromide, a new cholinesterase inhibitor, and RS 67333, a partial agonist of 5-HT4 receptors, enhances place and object recognition in young adult and old rats
L. Lamirault, C. Guillou, C. Thal, H. Simon
Progress in Neuro-Psychopharmacology & Biological Psychiatry 2003, 27, 185-195.

(-)-9-Dehydrogalanthaminium bromide, a new cholinesterase inhibitor, enhances place and object recognition memory in young and old rats
L. Lamirault, C. Guillou, C. Thal, H. Simon
Neurobiology of Learning and Memory 2003, 80, 113-122.

An efficient total synthesis of (±)-galanthamine
C. Guillou, J.-L. Beunard, E. Gras, C. Thal
Angew. Chem. Int. Ed. 2001, 40, 4745-4746.

Potent acetylcholinesterase inhibitors : Design, synthesis and structure-activity relationships of alkylene linked bis-galanthamine and galanthamine-galanthaminium salts
C. Guillou, A. Mary, D. Z. Renko, E. Gras, C. Thal
Bioorg. Med. Chem. Lett. 2000, 10, 637-639.

A formal synthesis of (±)-lycoramine via an intramolecular Heck reaction
E. Gras, C. Guillou, C. Thal
Tetrahedron Lett. 1999, 40, 9243-9244.

Reaction of cationic 1-substituted (η5-4-methoxycyclohexadienyl)(tricarbonyl)iron complexes with anilines : A revised mechanism
C. Guillou, F. Bintein, J.-P. Biron, C. Thal
Tetrahedron Lett. 1999, 40, 4331-4334.

Synthesis of 4-substituted-tricarbonyl(η4-cyclohexa-2,4-dien-1-one)iron complexes
V. Reboul, C. Guillou, C. Thal
Tetrahedron Lett. 1999, 40, 8355-8358.

Potent acetylcholinesterase inhibitors : Design, synthesis, and structure-activity relationships of bis-interacting ligands in the galanthamine series
A. Mary, D. Z. Renko, C. Guillou, C. Thal
Bioorg. Med. Chem. 1998, 6, 1835-1850.

Unexpected hydroxylation of galanthamine during the course of a Polonovski-Potier reaction
D. Renko, A. Mary, C. Guillou, P. Potier, C. Thal
Tetrahedron Lett. 1998, 39, 4251-4254.

Reactivity of cationic 1-substituted dicarbonyl (η5-4-methoxycyclohexadienyl)(triphenylphosphine)iron complexes
N. Millot, C. Guillou, C. Thal
Tetrahedron Lett. 1998, 39, 2325-2326.

Selective N-demethylation of galanthamine to norgalanthamine via a non classical Polonovski reaction
A. Mary, D. Z. Renko, C. Guillou, C. Thal
Tetrahedron Lett. 1997, 38, 5151-5152.

First synthesis and reactivity of phosphinite and phosphine bridge chelate dicarbonyl (η5-4-methoxycyclohexadienyl)iron complexes
N. Millot, C. Guillou, C. Thal
Tetrahedron 1997, 53, 12553-12564.

Trophic action of pharmacological substances with a guanidine group on mouse neuroblastoma cells and chick ganglionic neurons in culture
B. Pettmann, M. Escurat, C. Quirosa-Guillou, C. Thal, M.-M. Portier, M. Sensenbrenner
Neurosci. Lett. 1997, 230, 167-170.

Synthesis of cationic 1-substituted-dicarbonyl(η5-4-methoxycyclohexadienyl)(triphenylphosphine)iron complexes
C. Guillou, N. Millot, V. Reboul, C. Thal
Tetrahedron Lett. 1996, 37, 4515-4518.

A new etherification reaction in the η4-dienyltricarbonyliron series : Access to the 2,5-disubstituted-1,4-dioxane core
J. P. Lellouche, C. Quirosa-Guillou
Synth. Commun. 1995, 25, 977-993.

Increased axonal regrowth of lesioned rat sciatic nerve by veratrylguanidine methane sulfonate
U. Becherer, S. Kuchler-Bopp, F. Aubert, B. Rousseau, B. M. Riederer, D. Renko, C. Quirosa-Guillou, C. Thal, J.-P. Zanetta
Neurochem. Int. 1995, 26, 245-254.

Acyclic (η5-dienyl)tricarbonyliron(1+) cations generated in situ in the presence of molecular sieves : Modified reactivity with primary and secondary alcohols
C. Quirosa-Guillou, J.-P. Lellouche
J. Org. Chem. 1994, 59, 4693-4697.

Neurite outgrowth of neurons of rat dorsal root ganglia induced by new neurotrophic substances with guanidine group
S. Lehmann, C. Quirosa-Guillou, U. Becherer, C. Thal, J. P. Zanetta
Neurosci. Lett. 1993, 152, 57-60.

Reaction of guanidines with vicinal tricarbonyl compounds : Novel access to 2-aminoimidazole skeleton
C. Quirosa-Guillou, D. Z. Renko, C. Thal
Tetrahedron 1992, 48, 6385-6392.