|GROUP HOMEPAGE: http://tsvelikhovskyresearchgroup.shteeble.com
SYNTHETIC - MEDICINAL CHEMISTRY
MULTIPLE TARGETS VIA SELECTIVE TRANSFORMATIONS FROM A COMMMON MOLECULAR UNIT:
The unifying theme of our group is discovery and design of advanced molecular intermediates able to serve as common platforms for synthesis of various, structurally related (proceeding from same key subunit) compounds – potential therapeutic agents and drug candidates. Unlike existing classic synthetic “target-directed” methods, our constructing methodology will offer conceptually new perspective, enabling to deliver multiple targets via sequence of controlled, simple and atom economy reactions from a single common molecular unit; thus, providing simplified access to a wide variety of important classes of biologically active and structurally interesting molecules.
The presence of similar fundamental core structures is not exclusive to chemical compounds extracted from the same natural source. Common or highly resembling structures can be identified throughout various forms of life, such as different (and often distantly related) families of plants, as well as fungi and even bacteria. The cores (building blocks) will be identified, designed and synthesized, ultimately, to have an access to different classes of natural products and important biologically active compounds, as well as new techniques for the preparation of structurally unique novel molecules. All targets and transformations will be selected on the basis of novel molecular architecture, important biological activity, and the potential for mechanistic studies.
The list of simple elements of which one organism is primarily constructed - is not different from similar lists for all others
PROGRAM AND DESCIPLINES: Building upon the foundations of synthetic organic chemistry, the research program of our group will invoke a broad interdisciplinary collaboration with other fields such as, medicinal chemistry, organometallic chemistry, biochemistry, pharmacology and medicine.
1. Design and development of new reactions/transformations, catalysts, and synthetic methodologies.
2. Application of novel methodology through the synthesis of biologically important compounds, target-oriented total synthesis of natural products, and diversity oriented synthesis of natural product-like molecules and drug candidates. Molecules thus built will be employed in the investigation of biologically significant processes.
3. Mechanistic studies of novel synthetic transformations.
M.Sc. and Ph.D. Students, Postdocs
Students should have excellent background (M.Sc. or B.Sc.) in organic chemistry (prior research experience is an advantage). Applicants are required to submit a resume and copy of record of studies.
Students joining our laboratory will acquire extensive expertise in organic synthesis, spectroscopy (multinuclear NMR for characterization of organic compounds, IR, UV), and modern chromatographic systems and processing techniques (GC, GC/MS, LC, LC/MS, chiral chromatography, and many others). The goal of our group is to ensure that each student develops fully as a scientist, makes an impact on the forefront of science, and is successful in pursuing a career beyond the Hebrew University.
Dr. Dmitry Tsvelikhovsky
The Institute for Drug Research
School of Pharmacy, Room 416-a
Faculty of Medicine, Ein Karem
The Hebrew University of Jerusalem
Jerusalem, 91120 Israel
POSTDOCTORAL ASSOCIATE (2009 – 2011):
Department of Chemistry, Massachusetts Institute of Technology (MIT), Cambridge MA, USA.
(Research Advisor: Prof. Stephen L. Buchwald)
INDUSTRY (2004 – 2008):
Analytical R&D, Rafa Laboratories, Jerusalem, Israel.
EDUCATION (2000 – 2009):
Department of Chemistry, Faculty of Science, The Hebrew University of Jerusalem, Israel.
Ph.D. (2008, Research Advisor: Prof. Jochanan Blum)
M.Sc. (2005, Research Advisor: Prof. Jochanan Blum)
B.Sc. in Chemistry (2003) The Hebrew University of Jerusalem, Israel.
Tsvelikhovsky, D.; Buchwald, S. L., J. Am. Chem. Soc. 2011, 133, 14228
Concise Palladium-Catalyzed Synthesis of Dibenzodiazepines and Structural Analogues
Tsvelikhovsky, D.; Buchwald, S. L., J. Am. Chem. Soc. 2010, 132, 14048
Synthesis of Hetrocycles via Pd-Ligand Controlled Cyclization of 2-Chloro-N-(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines and Acridines
Publication Highlight: Science and Technology Concentrate in C&N News: “Ligands Dial in Ring Size”, Nov.1, 2010.
Rozin-Ben Baruch, A.; Tsvelikhovsky, D.; Schwarzeb, M.; Schomäckerb R.; Fanun, M.; Blum, J. J. Mol. Catal. A-Chem. 2010, 323, 65
Dependence of the Heck coupling in aqueous microemulsion by supported palladium acetate on the surfactant and on the hydrophobicity of the support
Tsvelikhovsky, D.; Popov, I.; Gutkin, V.; Rozin, A.; Shvartsman, A.; Blum, J. Eur. J. Org. Chem. 2008, 98
On the Involvement of Palladium Nanoparticles in the Heck and Suzuki Reactions
Tsvelikhovsky, D.; Pessing, D.; Avnir, D.; Blum J., Adv. Syn. Catal. 2008, 350, 2856
Forcing a cis-Product by Matrix Imprinting: Heck Reaction Catalyzed by Palladium Acetate Entrapped within cis-Imprinted Sol-Gel Derived Silicates
Tsvelikhovsky, D.; Blum, J., Eur. J. Org. Chem. 2008, 2017
Three Phase Microemulsion/Sol-Gel System for Aqueous C-C Coupling of Hydrophobic Substrates
Tsvelikhovsky, D.; Schumann, H.; Blum, J., Synthesis, 2006, 11, 1819
Cerium(IV)-Promoted Ethylation of Schiff Bases by Triethylaluminum
Tsvelikhovsky, D.; Gelman, D.; Molander, G. A.; Blum, J., Org. Lett. 2004, 6, 1995
Lanthanide-Promoted Ethylation of Schiff Bases by Triethylaluminum
Gelman, D.; Tsvelikhovsky, D.; Molander, G. A.; Blum, J. J. Org. Chem. 2002, 67, 6287
Palladium-Catalyzed Cross-Alkynylation of Aryl Bromides by Sodium Tetraalkynylaluminates