A5053505581- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Alkaloids: synthesis and pharmacology
- Asymmetric Synthesis and Catalysis
- Click Chemistry and Applications
- Traditional and Medicinal Uses of Annonaceae
- Chemical Synthesis and Analysis
- Marine Sponges and Natural Products
- Chemical synthesis and alkaloids
- Carbohydrate Chemistry and Synthesis
- Crystallography and molecular interactions
- Synthetic Organic Chemistry Methods
- Synthesis and Biological Evaluation
- Synthesis and biological activity
- Synthesis and Biological Activity
- Axial and Atropisomeric Chirality Synthesis
- Synthesis and Catalytic Reactions
- Metabolomics and Mass Spectrometry Studies
- Computational Drug Discovery Methods
- Bioinformatics and Genomic Networks
- Cancer therapeutics and mechanisms
- Photoreceptor and optogenetics research
- Analytical Chemistry and Chromatography
- Bioactive Compounds and Antitumor Agents
- Natural product bioactivities and synthesis
Université Paris-Saclay
2016-2025
Centre National de la Recherche Scientifique
2015-2025
Institut de Chimie des Substances Naturelles
2009-2021
Université Paris-Sud
2012-2020
Laboratoire d'Excellence en Recherche sur le Médicament et l'Innovation Thérapeutique
2012-2020
Laboratoire d'Énergétique Moléculaire et Macroscopique, Combustion
2014-2020
Laboratoire de Chimie Physique
2020
Laboratoire des Biomolécules
2016-2020
Pharmac
2014-2019
Laboratoire de Chimie
2014-2019
Chiral phosphoric acid-catalyzed asymmetric nitroso-Diels-Alder reaction of nitrosoarenes with carbamate-dienes afforded cis-3,6-disubstituted dihydro-1,2-oxazines in high yields excellent regio-, diastereo-, and enantioselectivities. Interestingly, we observed that the catalyst is able not only to control enantioselectivity but also reverse regioselectivity noncatalyzed reaction. The regiochemistry reversal asynchronous concerted mechanism were confirmed by DFT calculations.
As demonstrated by earlier successes with enamines, nitrogen-activated C=C double bonds have considerable potential for use in the construction of various nitrogen-containing products. To expand applications this class substrates, we focused on studying reactivity enamides and enecarbamates as promising representatives. Starting from well-known Povarov reaction, gradually developed other cycloaddition reactions and, more generally, an extended range methods α,β-difunctionalization. Our most...
The synthesis and structure–activity relationships associated with a series of 1,1-diarylethylene tubulin polymerization inhibitors 3 4 are described. key step for their preparation involves palladium-catalyzed coupling N-arylsulfonylhydrazones aryl halides, thus providing flexible convergent access to tri- tetrasubstituted 1,1-diarylolefins related isocombretastatin A-4 (isoCA-4). These compounds have been evaluated inhibitory activity as well cytotoxic activity. most potent...
Abstract A series of novel iso combretaquinazolines ( CoQ) 4 were quickly prepared by coupling N ‐toluenesulfonylhydrazones with 4‐chloroquinazolines under palladium catalysis. These compounds, which can be regarded as combretastatin A‐4 CA‐4) analogues that lack the 3,4,5‐trimethoxyphenyl ring, displayed nanomolar‐level cytotoxicity against various human cancer cell lines and observed to effectively inhibit tubulin polymerization. The CoQ compounds...
Three new monoterpene indole alkaloids (1-3) have been isolated from the bark of Geissospermum laeve, together with known (-)-leuconolam (4), geissolosimine (5), and geissospermine (6). The structures 1-3 were elucidated by analysis their HRMS NMR spectroscopic data. absolute configuration geissolaevine (1) was deduced comparison experimental theoretically calculated ECD spectra. isolation workflow guided a molecular networking-based dereplication strategy using an in-house database...
A highly efficient catalytic enantioselective [4+2] cycloaddition was developed between 2-benzothiazolimines and enecarbamates. wide range of benzothiazolopyrimidines bearing three contiguous stereogenic centers obtained in high to excellent yields with diastereo- enantioselectivities (d.r. > 98 : 2 up >99% ee). Furthermore, this chiral phosphoric acid-catalyzed strategy scalable enabled access a new class optically pure Lewis base isothiourea derivatives.
Dibenzopyrrocoline alkaloids, found in lauraceous and hernandiaceous plants, have been studied since the 1950s. The absolute configuration of these including cryptaustoline, has a topic debate due to conflicting studies. Having our laboratory some authentic samples dibenzopyrrocoline-type Cryptocarya we decided reinvestigate their using modern spectroscopic techniques along with TDDFT calculations. NMR reinvestigation sample cryptowolinol led us revise its relative ML-J-DP4 DP4+ analyses....
Abstract Guided by biosynthetic considerations, the total synthesis of dictazole B is reported for first time. Experimental evidence an easy access to challenging cyclobutane alkaloids marine origin, which are often postulated be precursors more complex structures, provided.
An efficient enantioselective construction of tetrahydronaphthalene-1,4-diones as well dihydronaphthalene-1,4-diols by a chiral phosphoric acid catalyzed quinone Diels-Alder reaction with dienecarbamates is reported. The nature the protecting group on diene key to success achieving high enantioselectivity. divergent "redox" selectivity controlled using an adequate amount quinones. Reversible redox switching without erosion enantioselectivity was possible from individual isomers.
Asymmetric synthesis of lemonomycinone amide (2) was accomplished from readily accessible starting materials. Enantioselective alkylation N-(diphenylmethylene)glycine tert-butyl ester (11) by 5-tert-butyldimethylsilyloxy-2,4-dimethoxy-3-methylbenzyl bromide (10) in the presence Corey-Lygo's phase transfer catalyst [O-(9)-ally-N-(9′-anthracenylmethyl) cinchonidium bromide, 0.1 equiv] afforded, after chemoselective hydrolysis imine function (THF/H2O/AcOH), substituted l-tert-butyl...
Theionbrunonines A and B (1 2), the first examples of monoterpene bisindole alkaloids linked by a thioether bridge, were isolated from stems Mostuea brunonis, guided molecular networking-based dereplication strategy. Their structures elucidated combination spectroscopic data ECD calculations. plausible biosynthetic pathway for 1 2 was postulated. 2) showed moderate antiplasmodial activities in micromolar range against strain FcB1 Plasmodium falciparum no cytotoxic activity MRC-5 cell line at 20 μM.
Five new monoterpene indole alkaloids (1–5), including four serpentinine-related bisindoles and one alstonine derivative monomer, have been isolated from the aerial parts of Picralima nitida. Their structures were elucidated by analysis their HRMS NMR spectroscopic data, absolute configurations deduced comparison experimental simulated ECD spectra. In addition, two known compounds (6 7), previously undescribed P. nitida, also purified. The compound isolation workflow was guided a molecular...
A library of functionalized 3-(α-styryl)-benzo[b]thiophenes, endowed with a high level molecular diversity, was efficiently synthesized by applying synthetic sequence that allowed introduction various substituents on aromatic A, B, and C-rings. The strategy developed involves the synthesis 3-bromobenzo[b]thiophene derivatives through bromocyclization step methylthio-containing alkynes using N-methylpyrrolidin-2-one hydrotribromide reagent (MPHT). Further coupling 3-bromobenzothiophenes under...
The synthesis of acetoxyendoperoxyacetal derivatives allowed the formation functionalized 3,5-disubstituted 1,2-dioxolanes through reactive peroxycarbenium species under Lewis acid mediation. introduction a neutral nucleophile such as allylsilane, silane, or silyl enol ether was accomplished with moderate to good yields. two studied acids, TiCl4 and SnCl4, gave contrasting results. higher diastereoselectivity toward trans diastereomer in experiments explained by faster degradation cis isomer...
Inaequalisines A and B (1 2), the first examples of hybrid alkylated phenylpropane monoterpene indole alkaloids, were isolated from roots Callichilia inaequalis, guided by combined use molecular networking substructure annotation. Their structures, including absolute configuration, elucidated spectroscopic methods ECD calculations. possible biosynthetic pathway for 1 2 was postulated.
Melonine is a basic monoterpene indole alkaloid (MIA) skeleton from Melodinus philliraeoides that was reported in 1983. The scarcity of its spectroscopic data questioned the validity structure. This prompted us to reisolate this molecule and revise structure into an unprecedented MIA scaffold. DFT-validated biosynthetic paths both new core originally form are proposed. pathway original melonine seems be thermodynamically feasible, compound may exist as natural product.
Functionalized 3-trifluoromethyl-2-isoxazolines and 3-trifluoromethylisoxazoles were easily prepared from trifluoromethyl aldoxime 2 under mild conditions by using DIB as oxidant. Theoretical studies of the reactivity trifluoroacetonitrile oxide 4 toward olefins alkynes carried out. The ring-opened with NaBH NiCl to yield corresponding trifluoromethylated γ-amino alcohols.
Macrophage migration inhibitory factor (MIF) is a key pleiotropic mediator and promising therapeutic target in cancer as well several inflammatory cardiovascular diseases including pulmonary arterial hypertension (PAH). Here, novel series of N-(phenylmethyl)-benzoxazol-2-thiones 5–32 designed to the MIF tautomerase active site was synthesized evaluated for its effects on cell survival. Investigation structure–activity relationship (SAR) particularly at 5-position benzoxazole core led...
Abstract Chemokines play critical roles in numerous physiologic and pathologic processes through their action on seven-transmembrane (TM) receptors. The N-terminal domain of chemokines, which is a key determinant signaling via its binding within pocket formed by receptors’ TM helices, can be the target proteolytic processing. An illustrative case this regulatory mechanism natural processing CXCL12 that generates chemokine variants lacking first two residues. Whereas such truncated behave as...