A5072804567- Oxidative Organic Chemistry Reactions
- Chemical Synthesis and Analysis
- Synthetic Organic Chemistry Methods
- Asymmetric Synthesis and Catalysis
- Marine Sponges and Natural Products
- Chemical synthesis and alkaloids
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Carbohydrate Chemistry and Synthesis
- Microbial Natural Products and Biosynthesis
- Synthesis and Catalytic Reactions
- Bioactive Compounds and Antitumor Agents
- Chemical Synthesis and Reactions
- Synthesis and Biological Evaluation
- Synthesis and Reactions of Organic Compounds
- Catalytic C–H Functionalization Methods
- RNA Interference and Gene Delivery
- Cancer therapeutics and mechanisms
- Traditional and Medicinal Uses of Annonaceae
- Alkaloids: synthesis and pharmacology
- Cyclopropane Reaction Mechanisms
- Fluorine in Organic Chemistry
- Catalytic Cross-Coupling Reactions
- Advanced Synthetic Organic Chemistry
- Synthesis and biological activity
University of British Columbia
2015-2024
iCo Therapeutics (Canada)
2024
Université de Sherbrooke
2024
Centre de Recherche en Cancérologie de Marseille
2023
Okanagan University College
2023
University of British Columbia Hospital
2021-2022
Université de Montpellier
2018
Universitat de València
2018
Universidad de Costa Rica
2018
University College Dublin
2018
The stem cell factor receptor, KIT, is a target for the treatment of cancer, mastocytosis, and inflammatory diseases. Here, we characterise in vitro vivo profiles masitinib (AB1010), novel phenylaminothiazole-type tyrosine kinase inhibitor that targets KIT.In vitro, had greater activity selectivity against KIT than imatinib, inhibiting recombinant human wild-type with an half inhibitory concentration (IC(50)) 200+/-40 nM blocking factor-induced proliferation phosphorylation IC(50) 150+/-80...
Iodobenzene diacetate in MeOH containing a catalytic amount of TFA efficiently oxidizes aldoximes to nitrile oxides. The latter may be trapped situ with olefins bimolecular or an intramolecular mode. new method enables the execution tandem oxidative dearomatization phenols/intramolecular oxide cycloaddition sequences leading useful synthetic intermediates.
This contribution reviews a family of reactions devised in our laboratory that effect the oxidative conversion phenols into 4-amido-dienones. A salient feature this chemistry is use hypervalent iodine reagents, especially diacetoxyiodobenzene (DIB), as uniquely capable oxidants context new transformation. The advent methodology has created opportunities alkaloid synthesis. Our efforts toward FR-901483, TAN-1251C, cylindricine C, and other nitrogenous natural products illustrate some...
All hyper: Recent advances in the area of chiral hypervalent iodine reagents, notably by groups Kita, Ishihara, and Fujita, enable some oxidative transformations to be conducted an enantioselective manner with asymmetric inductions range 86–95 % ee (see scheme, Mes=mesityl). This contribution highlights representative reactions, reagent/catalyst design, mechanistic aspects reported transformations.
Lipid nanoparticles (LNPs) are currently the most effective in vivo delivery systems for silencing target genes hepatocytes employing small interfering RNA. Antigen-presenting cells (APCs) also potential targets LNP siRNA. We examined uptake, intracellular trafficking, and gene potency primary bone marrow macrophages (bmMΦ) dendritic of siRNA formulated LNPs containing four different ionizable cationic lipids namely DLinDAP, DLinDMA, DLinK-DMA, DLinKC2-DMA. DLinKC2-DMA were potent...
A solution to the long-standing problem presented by oxidative cyclization of a phenolic 3-arylpropionamide spirolactam has been developed in this laboratory via oxazoline chemistry. This research was motivated our interest some novel tricyclic azaspirane natural products formally derived from tyrosine, such as FR901483 and TAN1251C. In paper, we disclose full details total synthesis these substances.
A common intermediate was used in the total syntheses of (−)-cylindricine C and (−)-2-epicylindricine (see picture) a process that involves initial oxidative spirocyclization phenolic sulfonamide. The remainder molecules is constructed through interesting sulfonamide chemistry. Supporting information for this article available on WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z460178_s.pdf or from author. Please note: publisher not responsible content functionality any supporting...
The androgen receptor (AR) plays a critical role in the progression of prostate cancer. Silencing this protein using short-hairpin RNA (shRNA) has been correlated with tumor growth inhibition and decreases serum specific antigen (PSA). In our study, we have investigated ability lipid nanoparticle (LNP) formulations small-interfering (siRNA) to silence AR human cell lines vitro LNCaP xenograft tumors following intravenous (i.v.) injection. screening studies panel cationic lipids showed that...
Abstract Successfully employing small interfering RNA (siRNA) therapeutics requires the use of nanotechnology for efficient intracellular delivery. Lipid nanoparticles (LNPs) have enabled approval various nucleic acid therapeutics. A major advantage LNPs is interchangeability its building blocks and payload, which allow it to be a highly modular system. In addition, drug derivatization approaches can used synthesize lipophilic molecule prodrugs that stably incorporate in LNPs. This provides...
The furan nucleus may be considered as a latent 1,4-dicarbonyl group. Expression of this functional equivalence within generic 2-furylamide results in formation nitrogen heterocycles reaction that termed the "Aza-Achmatowicz rearrangement", by analogy with similar transformations furylcarbinols. Aza-Achmatowicz products created enantioselective form chemoenzymatic methods, and are useful intermediates synthesis novel carbacephems, unusual aminoacids, azasaccharides, piperidine izidine...
The oxidative cyclization of a phenolic amide to spirolactam has long been regarded as an "impossible" reaction, because exposure the substrates variety oxidants results in formation spirolactones with consequent loss amine segment. We recently communicated that this heretofore unknown transformation may be achieved by oxidation oxazoline analogues and indolic amides. Herein, we provide full details our work.
An efficient iterative synthesis of oxazoles involves the cyclization 2-alkynyl glycinates (see scheme) formed from reaction 1-alkynyl aluminum reagents with α-chloroglycinates. This approach was used in total bisoxazole natural product, (−)-muscoride A.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTIntramolecular arylations of soft enolates catalyzed by zerovalent palladiumMarco A. Ciufolini, Hong Bo Qi, and Margaret E. BrowneCite this: J. Org. Chem. 1988, 53, 17, 4149–4151Publication Date (Print):August 1, 1988Publication History Published online1 May 2002Published inissue 1 August 1988https://pubs.acs.org/doi/10.1021/jo00252a064https://doi.org/10.1021/jo00252a064research-articleACS PublicationsRequest reuse permissionsArticle...
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTChemoenzymic synthesis of chiral furan derivatives: useful building blocks for optically active structuresDale G. Drueckhammer, Carlos F. Barbas III, Kenji Nozaki, Chi Huey Wong, Cynthia Y. Wood, and Marco A. CiufoliniCite this: J. Org. Chem. 1988, 53, 8, 1607–1611Publication Date (Print):April 1, 1988Publication History Published online1 May 2002Published inissue 1 April...
Upon reaction with PhI(OAc)2, α-oxo-aldoximes are oxidized to α-oxo-nitrile oxides, while α-oxo-ketoximes converted into nitrile oxides via the oxidative cleavage of carbonyl−imino σ bond. The thus formed were trapped norbornene or styrene in good yield. α,α′-Dioxo-ketoximes react less efficiently.
Fifty years after the discovery of thiopeptide antibiotic micrococcin P1, constitutional and stereochemical uncertainties concerning its structure have been lifted with total synthesis absolute assignment (see picture).
A full account of the oxidative dearomatization para- and ortho-phenolic sulfonamides is provided together with an overview chemistry products their elaboration to building blocks for spirocyclic alkaloids. concise total synthesis putative lepadiformine complements discussion.
Abstract The catalytic, enantioselective oxidative cyclization of naphthol‐derived carboxylic acids mediated by chiral hypervalent iodine reagents has been studied extensively in the recent past, but analogous reactions non‐carboxylic substrates are yet unknown. This paper describes a enantioselective, iodine‐promoted cycloetherification reaction naphtholic alcohols. new process relies on variant Uyanik–Ishihara catalyst, which stereogenic centers have relocated closer to atom. catalyst...
This paper describes a synthesis of ALC-0315 by sequence that more than doubles the overall yield relative to published one, and employs much cleaner reactions, thereby facilitating purifications considerable extent.
Lipid nanoparticles (LNPs) have proven to be promising delivery vehicles for RNA-based vaccines and therapeutics, particularly in LNP formulations containing ionizable cationic lipids that undergo protonation/deprotonation response buffer pH changes. These are typically formulated using a rapid mixing technique at low pH, followed by return physiological triggers LNP-LNP fusion. A detailed understanding of these dynamic processes is crucial optimize the overall performance efficiency LNPs....