A5071730193- Catalytic C–H Functionalization Methods
- Catalytic Cross-Coupling Reactions
- Catalytic Alkyne Reactions
- Chemical Synthesis and Reactions
- Synthesis and biological activity
- Cyclopropane Reaction Mechanisms
- Organoboron and organosilicon chemistry
- Sulfur-Based Synthesis Techniques
- Synthesis and Biological Evaluation
- Synthesis and Catalytic Reactions
- Synthetic Organic Chemistry Methods
- Chemical Synthesis and Analysis
- Oxidative Organic Chemistry Reactions
- Cancer therapeutics and mechanisms
- Malaria Research and Control
- Synthesis and Biological Activity
- Marine Sponges and Natural Products
- Asymmetric Synthesis and Catalysis
- Synthesis of Indole Derivatives
- Crystallization and Solubility Studies
- Bioactive Compounds and Antitumor Agents
- X-ray Diffraction in Crystallography
- Multicomponent Synthesis of Heterocycles
- Vanadium and Halogenation Chemistry
- Synthesis of Organic Compounds
Université Paris-Saclay
2016-2025
Centre National de la Recherche Scientifique
2015-2024
Laboratoire des Biomolécules
2008-2022
Laboratoire d'Énergétique Moléculaire et Macroscopique, Combustion
1997-2021
Pharmac
2021
Université Paris-Sud
2010-2019
La Ligue Contre le Cancer
2014-2019
Laboratoire de Chimie
1993-2017
Institut Galien Paris-Saclay
2005-2014
Laboratoire de Chimie Physique
2007-2013
Herein is reported a convergent synthesis of isocombretastatins A, novel class potent antitubulin agents. These compounds having 1,1-diarylethylene scaffold constitute the simplest isomers natural Z-combretastatins A that are easy to synthesize without need control Z-olefin geometry. The discovery isoCA-4 with biological activities comparable CA-4 represents major progress in this field.
Abstract The cytotoxic activity of a series 23 new isoerianin derivatives with modifications on both the A and B rings was studied. Several compounds exhibited excellent antiproliferative at nanomolar concentrations against panel human cancer cell lines. most compound, ( 3 ), strongly inhibits tubulin polymerization in micromolar range. Moreover, leads to G 2 /M phase cell‐cycle arrest H1299 K562 cells, induces apoptosis. Isoerianin also disrupts vessel‐like structures formed by umbilical...
Drug delivery of combined cytotoxic and antivascular chemotherapies in multidrug nanoassemblies may represent an attractive way to improve the treatment experimental cancers. Here we made proof concept this approach on LS174-T human colon carcinoma xenograft nude mice model. Briefly, have nanoprecipitated anticancer compound gemcitabine conjugated with squalene (SQ-gem) together isocombretastatin A-4 (isoCA-4), a new isomer combretastatin (CA-4). It was found that these molecules...
In this Review, we present an overview of hydrostannation alkynes until the end 2018. The mechanism tin hydride addition on a triple bond in presence metal catalysts as Pd, Ru-based complexes, Lewis acids, and under radical conditions is discussed at beginning Review. Then, discuss stereoselectivity well regioselectivity aspects carbon using metal-catalysis, conditions, or acids. each these items, reactions will be studied for terminal then internal alkynes. Applications metal-catalysis...
The cytotoxic activities of 23 new isocombretastatin A derivatives with modifications on the B-ring were investigated. Several compounds exhibited excellent antiproliferative activity at nanomolar concentrations against a panel human cancer cell lines. Compounds isoFCA-4 (2 e), isoCA-4 k) and isoNH(2)CA-4 s) most cytotoxic, strongly inhibited tubulin polymerization IC(50) values 4, 2 1.5 microM, respectively. These found to be 10-fold more active than phenstatin colchicine respect growth...
The first platinum-catalyzed selective silylation of aryl halides including iodides and bromides having an electron-withdrawing group is described. reaction takes place rapidly in NMP with triethylsilane as a silicon source sodium acetate to provide functionalized aryltriethylsilanes moderate good yields. Heteroaromatic also were found be readily silylated triethylsilane. procedure chemoselective tolerates wide variety functional groups.
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...
We report the synthesis and metabolic biological evaluation of a series 17 novel heterocyclic derivatives isocombretastatin-A4 (iso-CA-4) their structure-activity relationships. Among these derivatives, most active compound, 4f, inhibited growth panel seven cancer cell lines with an IC50 in low nanomolar range. In addition, 4f showed interesting activity against CA-4-resistant colon-carcinoma cells multidrug-resistant leukemia cells. It also induced G2/M cell-cycle arrest. Structural data...
[chemical reaction: see text]. PtO2- and H2PtCl6-catalyzed hydrosilylation of internal aryl alkynes having a para or an ortho substituent with triethylsilane are discussed compared. The regioselectivity the H-Si bond addition was found to be controlled by rather than nature platinum catalyst. Arylalkynes substituent, regardless its electronic nature, directed silyl mainly alpha-position. PtO2 proved versatile powerful catalyst compared H2PtCl6 since it prevents alkyne reduction.
The reactivity of sterically hindered N-tosylhydrazones 2 featuring ortho/ortho′-substituents on the aromatic ring with various ortho-, meta-, and para-substituted aryl halides 3 was investigated. To accomplish successfully this challenging coupling, fine-tuning reaction conditions were required. newly established PdCl2(MeCN)2/Xphos/NaO-t-Bu/F-benzene system in a sealed tube is compatible broad spectrum both coupling partners, regardless their electronic steric nature. This protocol has been...
Unveiling a Mo-catalyzed synthesis, unprecedented anticancer dihydroindolo[1,2- c ]-quinazolines and dihydroindolo[3,2- b ]-indoles were discovered from N -vinylazoles.
The development of novel therapeutic strategies enabling the selective destruction tumors while sparing healthy tissues is great interest to improve efficacy cancer chemotherapy. In this context, we designed a β‐glucuronidase‐responsive albumin‐binding prodrug programmed release potent Isocombretastatin A‐4 analog within tumor microenvironment. When injected at non‐toxic dose in mice bearing orthotopic triple‐negative mammary tumors, produced significant anticancer activity, therefore...