We investigated how many cases of the same chemical sold as different products (at possibly different prices) occurred in a prototypical large aggregated database and simultaneously tested the tautomerism definitions in the chemoinformatics toolkit CACTVS. We applied the standard CACTVS tautomeric transforms plus a set of recently developed ring–chain transforms to the Aldrich Market Select (AMS) database of 6 million screening samples and building blocks. In 30 000 cases, two or more AMS products were found to be just different tautomeric forms of the same compound. We purchased and analyzed 166 such tautomer pairs and triplets by ¹H and ¹³C NMR to determine whether the CACTVS transforms accurately predicted what is the same “stuff in the bottle”. Essentially all prototropic transforms with examples in the AMS were confirmed. Some of the ring–chain transforms were found to be too “aggressive”, i.e. to equate structures with one another that were different compounds.

Experimental and Chemoinformatics Study of Tautomerism in a Database of Commercially Available Screening Samples

Laura Guasch^†, Waruna Yapamudiyansel^†, Megan L. Peach^§, James A. Kelley^†, Joseph J. BarchiJr.^†, and Marc C. Nicklaus^*^†

^† Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Frederick, Maryland 21702, United States

^§ Basic Science Program, Chemical Biology Laboratory, Leidos Biomedical Inc., Frederick National Laboratory for Cancer Research, Frederick, Maryland 21702, United States

J. Chem. Inf. Model., Article ASAP

DOI: 10.1021/acs.jcim.6b00338, http://pubs.acs.org/doi/full/10.1021/acs.jcim.6b00338

Publication Date (Web): September 26, 2016

*E-mail: mn1@helix.nih.gov.

Laura Guasch
Chemoinformatics Data Scientist
National Institutes of Health
National Cancer Institute (NCI): National Institute of Health
Bethesda, MD, United States
https://www.researchgate.net/profile/Laura_Guasch, https://uk.linkedin.com/in/lguasch
a highly motivated computational chemist and cheminformatician that employ, analyze, and develop computer-based methods to aid in the drug discovery. I enjoy working with experimentalists from the fields of biology, pharmacy, medicine and chemistry on answering relevant questions in drug discovery.
Specialties: CADD; Virtual screening; Pharmacophores; Docking; Homology modeling; Quantum chemistry; SAR/QSAR; ADME/Tox modeling; Drug metabolism; Chemoinformatics; Data mining; Molecular informatics.

Research experience
Feb 2012–present PostDoc Position
National Institutes of Health · National Cancer Institute (NCI): National Institute of Health · Chemical Biology Laboratory
United States · Frederick
Development of novel approaches for tautomerism analysis. Structure-based and ligand-based identification and design of anti-cancer and anti-viral agents.
Jan 2009–Jun 2009 Research Intern
University of Innsbruck · Institute of General, Inorganic and Theoretical Chemistry · Theoretical Chemistry
Austria · Innsbruck
Discovery of Natural Product PPAR-gamma Partial Agonists by a Pharmacophore-Based Virtual Screening Workflow.
Sep 2007–Dec 2011 PhD Student
Universitat Rovira i Virgili · Department of Biochemistry and Biotechnology · Nutrigenomics Research Group
Spain · Tarragona
Identification of natural products as antidiabetic agents using computer-aided drug design methods.
Jan 2007–Jun 2007 Research Fellow
Universitat Rovira i Virgili · Department of Physical and Inorganic Chemistry · Quantum Chemistry Group
Spain · Tarragona
Prediction of enantiomeric excesses in asymmetric catalysis using a new QSSR approach based on three-dimensional DFT molecular descriptors
Jul 2006–Aug 2006 Summer Intership
Barcelona Science Park · Quantum Simulation of Biological Processes
Spain · Barcelona
Structure and electronic configuration of compound I intermediates Penicillium vitale catalases using techniques of molecular dynamics simulation


Education
Sep 2007–Jun 2008 Universitat Rovira i Virgili
Nutrition and Metabolism · Master of Science
Spain · Tarragona
Sep 2004–Jun 2007 Universitat Rovira i Virgili
Biochemistry · BSc
Spain · Tarragona
Sep 2002–Jun 2007 Universitat Rovira i Virgili
Chemistry · Bachelor of Science
Spain · Tarragona


Awards & achievements
Dec 2011 Award: European Doctorate Mention
Dec 2011 Award: PhD Extraordinary Award

Marc C. Nicklaus, Ph.D.
Senior Scientist
Chemical Biology Laboratory
Head, Computer-Aided Drug Design (CADD) Group
Dr. Nicklaus received his Ph.D. in applied physics from the Eberhards-Karls-Universitat, Tubingen, Germany, and then served as a postdoctoral fellow in the Molecular Modeling Section of the then called Laboratory of Medicinal Chemistry, NCI. He became a staff fellow in 1998, and a Senior Scientist in 2002. In 2000, he founded, and has been heading since then, the Computer-Aided Drug Design (CADD) Group.
Dr. Nicklaus pioneered work on making large small-molecule databases and related chemoinformatics tools available to the scientific public on the CADD Group’s web server. He also pioneered the analysis of conformational energies of small molecule ligands bound to proteins. As Head of the CADD Group, he oversees the group’s research program in chemoinformatics, fundamentals of protein-ligand interactions, and in silico screening for targets of high interest to NCI. He makes the latter resources available in collaborative projects to improve NCI’s efforts in hit identification and drug design.
Link to additional information about Dr. Nicklaus’ research.
Areas of Expertise
1) chemoinformatics, 2) small-molecule databases, 3) protein-ligand interactions, 4) (quantitative) structure-activity relationships, 5) computer-aided drug design, 6) computational chemistry
CONTACT INFO
Marc C. Nicklaus, Ph.D.

Center for Cancer Research

National Cancer Institute

Building 376, Room 207

Frederick, MD 21702-1201

Ph: 301-846-5903
mn2z@nih.gov(link sends e-mail)
PERMALINK


Research
Publications
Biography
Team

Computer-Aided Drug Design. The Computer-Aided Drug Design (CADD) Group is a research unit within the Chemical Biology Laboratory (CBL) that employs, analyzes, and develops computer-based methods to aid in the drug discovery, design, and development projects of the CBL and other researchers at the NIH. We split our efforts about evenly between support-type projects and research projects initiated and conducted by CADD staff members. We are implementing many projects, and making available resources developed by the CADD Group, in a Web-based manner. This offers three advantages: (1) it frees all users, including the group members themselves, from platform restraints and the concomitant expenses for specific software/hardware, (2) it makes resources and results immediately available for sharing among all collaborators regardless of their location, and (3) helps, without additional effort, further the mission of the NCI as a publicly funded institution by providing data and services directly to the (scientific) public.
Chemical Identifier Resolver (CIR). CIR works as a resolver for many different chemical structure identifiers (e.g. chemical names, InChI, SMILES etc.) and allows one to convert the given structure identifier into a full structure representation or another structure identifier including references to particular databases in which the corresponding structure or structure identifier occurs. CIR offers a simple to use, programmatic application programming interface (API) based on URLs requested by HTTP. This allows easy linking of CIR and its content to other scientific web services and program packages. CIR currently provides access to 120 million structure records.
Enhanced NCI Database Browser. The Enhanced NCI Database Browser can be used to search the 250,000-compound Open NCI Database. This dataset is the publicly available part of the half-million structure collection assembled by the NCI’s Developmental Therapeutics Program during the program’s 50+ years of screening compounds against cancer and, more recently, AIDS. Visit the CADD Group’s home page or the Enhanced NCI Database Browser service for more information.
Fundamentals of Protein-Ligand Interactions. The non-covalent binding of a drug to the binding site of an enzyme (or other biomacromolecule) is the fundamental process of most drug actions. In spite of a vast body of experimental data available on protein-ligand complexes, mostly obtained by X-ray crystallography, there are still open questions of how this binding process occurs at the atomic and quantitative energetic level. One of the issues is the range of conformational energies one can expect to find for the small-molecule ligand bound to proteins, which we found to be higher than generally assumed. This has led us to broader questions regarding x-ray crystallographic methodologies, such as whether quantum-mechanical refinement (or re-refinement) of protein ligand structures may improve structural quality in various ways.
HIV Integrase. A long-standing interest of our group has been HIV integrase (IN) as a drug development target. This enzyme catalyzes the integration of the viral DNA into the human DNA, which is an essential step in the viral replication cycle. Only a handful of approved drugs so far are based on IN inhibition. We have been utilizing all available experimental results, be they structural, mechanistic, or biochemical, to model and better understand inhibition of IN by small molecules. A recent expansion of these efforts is our work aimed at developing HIV microbicides for the prevention of infection with HIV by topical application such as vaginal gels.
Among our main collaborators are Stephen Hughes and Yves Pommier, NCI; Wolf-Dietrich Ihlenfeldt, Xemistry, Germany; Vladimir Poroikov, Russian Academy of Medical Sciences, Moscow; and Raul Cachau, Leidos, FNLCR.
Scientific Focus Areas:
Biomedical Engineering and Biophysics, Chemical Biology, Computational Biology, Structural Biology

/////////////Experimental, Chemoinformatics, Tautomerism, Database, Commercially Available, Screening Samples

ARKIVOC Volume 2006
Part (v): Commemorative Issue in Honor of
Facilitator: Luba Ignatovich
Scientific Editor: Mikael Begtrup

2. The structure of Omeprazole in the solid state: a 13C and 15N NMR/CPMAS study (EL-1719AP)
Rosa M. Claramunt, Concepción López and José Elguero
Full Text: PDF (193K)
pp. 5 – 11

The structure of Omeprazole in the solid state: a 13C and 15N NMR/CPMAS study

Rosa M. Claramunt,a Concepción López,a and José Elguero b *

a Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Senda del Rey 9, E-28040 Madrid, Spain

b Instituto de Química Médica, CSIC, Juan de la Cierva, 3. E-28006 Madrid, Spain E-mail: iqmbe17@iqm.csic.es

To our friend Professor Edmunds Lukevics on his 70th anniversary

Edmunds Lukevics

Abstract

The 13C and 15N CPMAS spectra of a solid sample of Omeprazole have been recorded and all the signals assigned. The sample consists uniquely of the 6-methoxy tautomer. For analytical purposes, the signals of the other tautomer, the 5-methoxy one, were estimated from the data in solution (Magn. Reson. Chem. 2004, 42, 712).

Keywords: Omeprazole, NMR, 13C, 15N, CPMAS, tautomerism, benzimidazole

see at

http://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/2006/5/graphical-abstracts/

http://www.arkat-usa.org/get-file/22955/

Edmunds LUKEVICS

(14.12.1936 – 21.11.2009)

Professor Edmunds LUKEVICS
Latvian Institute of Organic Synthesis,
Head of the Laboratory of Organometallic ChemistryAizkraukles iela 21,
Riga, LV-1006
Latvia

Born: December 14, 1936, Liepaja, Latvia
Departed: November 21, 2009, Riga, Latvia

Interests:

Organometallic Compounds
Heterocyclic Compounds
Biological Activity of Organic Compounds

Main Research:

Development of methods for the synthesis of organosilicon and -germanium derivatives of furan, thiophene and nitrogen-containing heterocycles ; study of the influence of organosilicon ,-germanium and -tin substituents on the direction of substitution and addition reactions of furan and thiophene derivatives ; study of hydrosilylation and hydrogermylation reactions, synthesis and investigation of properties of penta- and hexacoordinated organosilicon and -germanium derivatives; application of alkenyl silanes and germanes in the synthesis of nitrogen-containing heterocycles; application of phase-transfer catalysis and ultrasonic irradiation in organometallic synthesis; synthesis of biologically active organosilicon and organogermanium compounds and studies of their properties.

Education:

University of Latvia (Faculty of Chemistry), 1958
Dr.chem. (Candidate of Science in former USSR, Ph.D. in Western countries), Latvian Academy of Sciences, Riga, 1966
Dr.habil.chem. (Doctor of Science in former USSR), Latvian Academy of Sciences, Riga, 1973

Experience:

Latvian Institute of Organic Synthesis –

Junior Researcher, 1958-1967
Senior Researcher, 1968-1970
Head, Laboratory of Organometallic Chemistry, 1970 – 2009
Vice-director, 1980-1982
Director, 1982 – 2003

Honours and Awards:

Corresponding Member, Latvian Academy of Sciences , 1982
Full Member, Latvian Academy of Sciences , 1987
Member, New York Academy of Sciences, 1993
The Latvian Academy of Sciences Gustavs Vanags Prize (in Chemistry), 1986
Latvian SSR State Prize, 1974, 1989
S.Hiller Medal (Latvian Institute of Organic Synthesis), 1990
G.Vanags Medal (Riga Technical University), 1991
D.H.Grindel Medal (company ‘Grindex’, Latvia), 1995
L.Liepina Medal (Institute of Inorganic Chemistry, Riga), 1996
The Latvian Academy of Sciences Grand Medal, 1996
Silver Medal of Milan University, 1996
Schmiedebergs Medal (Latvian Pharmacological Society), 1998
The Latvian Academy of Sciences and Company “GRINDEX” Prize, 1999
Paul Walden’s Medal (Riga Technical University), 2000
Latvian Academy of Sciences Presidium Award, 1971, 1973, 1977, 1981, 1982, 1985,1987, 1989, 1992
International Man of the Year (The International Biographic Centre of Cambridge, England), 1992-1993, 1994-1995
Man of the Year (The American Biographical Institute), 1994, 2005
The first-level Badge of Honour of the Order of Three Stars, 1997
Company “Grindex” gold badge of honour, 2001
The Cabinet of Ministers of the Republic of Latvia Prize , 2004
American Medal of Honor (ABI), 2005
Gold Medal for Latvia (ABI), 2006
The Plato Award (IBC), 2006
Man of Achievement (ABI), 2007

Professional Activities:

Member of Presidium and Senate, Latvian Academy of Sciences, 1987-1991
Member of Board, Division of Chemical and Biological Sciences, Latvian Academy of Sciences, 1983-1993
Member, Latvian Academy of Sciences Commission on Terminology, 1987- 1999
Chairman, Habilitation and Promotion Council (Chemistry and Pharmacy), Latvian Institute of Organic Synthesis, 1994 -1999
Member (Chairman,1991-1993, 1997-2002), Latvian Council of Science Expert Committee for Chemistry, 1991 – 2006
Vice-chairman, Habilitation and Promotion Council (Chemistry), University of Latvia, 1998- 2009
Member of Editorial Board for:

Khimiya Geterotsikicheskikh. Soedinenii (Chemistry of Heterocyclic Compounds, Springer), 1980-1985; Editor-in-chief, 1985 – 2009
Proceedings of Latvian Academy of Sciences, 1982-1990
Latvian Journal of Chemistry, 1991 – 2009
Bioorganicheskaya Khimiya, 1989 – 1993
Applied Organometallic Chemistry, 1990 – 2009
Main Group Metal Chemistry, 1992 – 2009
Metal-Based Drugs, 1993 – 2003
Mendeleev Communications, 1994 – 2009
Advances in Heterocyclic Chemistry, 1994 – 2009
Silicon Chemistry, 2001-2007
Arkivoc, 2001 – 2009
Bioinorganic Chemistry and Applications, 2003 – 2006
Heterocyclic Communications, 2005 – 2009
Molecules, 2008 – 2009
Journal of Organic and Pharmaceutical Chemistry (Ukraine), 2009 – 2009

Chairman, Scientific Council “Chemistry and Technology of Sulfur Organic Compounds”, USSR State Committee of Science and Technics, 1982-1987
Chairman, Council “Application of Organometallic Compounds in National Economy”, USSR (Russian) Academy of Sciences, 1984-1992
Member, United Libraries Informative Council, USSR Academy of Sciences, 1985-1990
Member, Scientific Council “Physiologically Active Compounds”, USSR Academy of Sciences, 1986-1992
Member, Scientific and Technical Council, USSR Ministry of Medical and Microbiological Industry, 1987-1990
Member, Soviet National Committee on collecting and estimating information in science and technics “CODATA”, 1987-1990
Member of Council for Coordination of scientific work, Department of Biochemistry, Biophysics and Physiologically Active Compounds, USSR Academy of Sciences, 1988-1991
Member of International Organizing Committees
– International Conference on the Coordination and Organometallic Chemistry of Germanium, Tin and Lead, 1992, 1995, 1998, 2001
– International Symposium on Organosilicon Chemistry, 1993, 1996, 1999, 2002, 2005, 2008.

Memberships:

Member of Organometallic Chemistry Division, Federation of European Chemical Societies, 1995-2005
Member of Organometallic Chemistry Division, European Association for Chemical & Molecular Sciences, 2006
Member, Latvian Chemical Society, 1995
Member, American Chemical Society, 1997
Member, National Geographic Society, 1997
Honorary Member, Pharmacological Society of Latvia, 1998

Lectures

Invited Lectures at Universities

Indian Institute of Science, Bangalore (India), 1989
Indian Institute of Technology, Bombay (India), 1989
University of Dresden (Germany), 1989
Universities of Bordeaux, Tolouse, Montpellier, Marseilles (France), 1990, 1994
University of Lund (Sweden), 1992
University of Alcala de Henares ( Spain), 1993
Tohoku University (Sendai, Japan), 1991, 1992
Tokyo University of Science (Japan), 1997
Kyoto University (Japan), 1997
Universities of Kyoto and Kanagawa, Japan, 2002.

Invited Lectures and Symposium’s Plenary Lectures:

40th Nobel Symposium (Lidingö, Sweden), 1977
VI Symposium on Chemistry of Heterocyclic Compounds (Brno, Czechoslovakia), 1978
7th International Symposium on Organosilicon Chemistry (Kyoto, Japan), 1984
VI FECHEM Conference on Organometallic Chemistry (riga, Latvia), 1985
II Soviet-Indian Symposium on Organometallic Chemistry( Irkutsk, Russia), 1989
17th DDR-Poland Colloquy on Organometallic Chemistry (Holzhau, Germany), 1989
6th International Conference on Organometallic and Coordination Chemistry of Germanium, Tin and Lead (Brussels, Belgium), 1989
Huang Minlon Symposium on Organic Chemistry (Shanghai, China), 1989
International Chemical Conference on Silicon and Tin ( Kuala Lumpur, Malaisia), 1989
9th International Symposium on Organosilicon Chemistry (Edinburgh, UK), 1990
1st Meeting of the European Society of Sonochemistry, Autrans (Grenoble, France), 1990
11th International Symposium on Medicinal Chemistry (Jerusalem, Israel), 1990
S.Hiller Memorial Lectures (Riga, Latvia), 1990
1st Meeting of Japanese Germanium Discussion Group (Tokyo, Japan), 1991
International Conference on Environmental and Biological Aspects of Maingroups Organometals (Padua, Italy), 1991
3rd Swedish-German workshop: Nucleic Acid Synthesis, Structure and Function (Uppsala, Sweden), 1992
2nd ANAIC Conference on Materials Science and Environmental Chemistry of Main Group Elements (Kual Lumpur, Malaysia), 1993
Todai Symposium “Ge-Sn-Pb Tokyo’93”: International Symposium on Organic, Bioorganic and Bioinorganic Chemistry of Compounds of higher row Group 14-elements (Tokyo, Japan), 1993
10th International Symposium on Organosilicon Chemistry (Poznan, Poland), 1993
3rd Meeting of the European Society of Sonochemistry (Figueira da Foz, Portugal), 1993
14th Nordic Meeting of Structural Chemists (Helsinki, Finland), 1993
8th International Conference on the Organometallic Chemistry of Germanium, Tin and Lead (Sendai, Japan), 1995
8th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (Santa Barbara, USA), 1995
8th Symposium Heterocycles in Bioorganic Chemistry (Como, Italy), 1996
9th International Conference on the Coordination and Organometallic Chemistry of Germanium, Tin, and Lead (Melbourne, Australia), 1998
12th International Conference on Organosilicon Chemistry (Sendai, Japan), 1999
International Conference on Organic Synthesis “Balticum Organicum Sinteticum-2000″(Vilnius, Lithuania), 2000
X International Symposium “Jubilee Krka Prizes” (Novo Mesto, Slovenia), 2000

Recent/Representative Publications:

E.Ya. Lukevits, M.G.Voronkov. Organic Insertion Reactions of Group IV Elements, 1966, New York: Consultants Bureau, 413 pp.
S.N.Borisov, M.G.Voronkov, E.Ya.Lukevits. Organosilicon Heteropolymers and Heterocompounds, 1970, NewYork: Plenum Press, 633 pp.
S.N.Borisov, M.G.Voronkov, E.Ya.Lukevits. Organosilicon Derivatives of Phosphorus and Sulfur, 1971, NewYork; London: Plenum Press, 343 pp.
M.G.Voronkov, G.I..Zelchan, E.Ya.Lukevits. Silizium und Leben, 1975, Berlin: Akademie-Verlag, 370 pp.
E.Lukevics, O.Pudova, R.Sturkovich. Molecular Structure of Organosilicon Compounds, 1989, Chichester: Ellis Horwood Ltd., 359 pp.
E.Lukevics, T.Gar, L.Ignatovich, V.Mironov. Biological Activity of Germanium Compounds, 1990, Riga: Zinatne, 191 pp. (in Russian).
E.Lukevics, A.Zablocka. Nucleoside Synthesis: Organosilicon Methods, 1991, Chichester: Ellis Horwood, 496 pp.
E.Lukevics, L.Ignatovich. Biological activity of organogermanium compounds. – In: The Chemistry of Organic Germanium, Tin and Lead Compounds/Ed. Z.Rappoport/, Wiley, Chichester, 2002, vol. 2, pt. 2, pp. 1653-1683.
E.Lukevics, O.Pudova. Biological activity of organogermanium compounds. – In: The Chemistry of Organic Germanium, Tin and Lead Compounds/Ed. Z.Rappoport/, Wiley, Chichester, 2002, vol. 2, pt. 2, pp. 1685-1714.

E.Lukevics, O.Pudova. Silyl imidic esters. – In: Science of Synthesis, Thieme, 2002, vol. 4, pp. 305-315.
E. Lukevics, P. Arsenyan, S. Belyakov, O. Pudova. Synthesis, structure and chemical transformations of ethynylgermatranes – Eur. J. Inorg. Chem., 2003, Iss.17, pp.3139-3143.
R. Abele, E. Abele, M. Fleisher, S. Grinberga, E. Lukevics. Novel fluoride ion mediated synthesis of unsymmetrical siloxanes under phase transfer catalysis conditions. – J. Organomet. Chem., 2003, vol.686, N 1/2, pp.52-57.
E. Lukevics, L. Ignatovich, I.Shestakova. Synthesis, psychotropic and anticancer activity of 2,2-dimethyl-5-[5-trialkylgermyl(silyl)-2’-hetarylidene]-1,3-dioxane-4,6-diones and their analogues. – Appl.Organomet. Chem., 2003, vol. 17, N 12, pp.898-905.
P. Arsenyan, K. Rubina, I. Shestakova, E. Abele, R. Abele, I. Domracheva, A. Nesterova, J. Popelis, E. Lukevics. Synthesis and cytotoxicity of silylalkylthio-substituted N-heterocycles and their hydroselenites. – Appl. Organomet. Chem., 2003, vol. 17, N 11, pp.825-830.
E. Lukevics, L. Ignatovich, T. Shul’ga, S. Belyakov. The crystal structure of 2-benzo[b]thienylgermatrane. – Appl. Organomet. Chem., 2003, vol. 17, N 9, pp.745-746.
K. Rubina, E. Abele, P. Arsenyan, M. Fleisher, J. Popelis, A. Gaukhman, E. Lukevics. The role of palladium catalyst and base in stereoselective tranformations of (E)-2-chlorovinylsulfides. –Tetrahedron, 2003, vol.59, N 38, pp.7603-7607.
I. Iovel, L. Golomba, J. Popelis, S. Grinberga, E. Lukevics Catalytic hydrosilylation of furan, thiophene, and pyridine aldimines. – Chem. Heterocycl. Comp., 2003, vol.39, N 1, pp.49-55.
G. Veinberg, M. Vorona, I. Shestakova, I. Kanepe, E. Lukevics. Design of ß-lactams with mechanism based nonbacterial activities. – Current Medicinal Chemistry, 2003, vol.10, N 17, pp.1741-1757.
E. Lukevics, P. Arsenyan, O. Pudova. Methods for the synthesis of oligothiophenes. – Heterocycles, 2003, vol.60, N 3, pp.663-687.
V.Dirnens, V.Klusa, J.Skuyins, S.Svirskis, S.Germane, A.Kemme, E.Lukevics. Synthesis and pharmacological activity of silyl isoxazolines-2. – Silicon Chemistry, 2003 (publ. 2004), vol. 2, N 1/2, pp. 11-25.
I.Iovel, L.Golomba, M.Fleischer, J.Popelis, S.Grinberga, E.Lukevics. Hydrosilylation of (hetero)aromatic aldimines in the presence of Pd(I) complex. – Chem.Heterocycl. Comp., 2004, vol. 40, N 6, pp. 701-714.
P.Arsenyan, O.Pudova, J.Popelis, E.Lukevics. Novel radial oligothienylsilanes. – Tetrahedron Lett., 2004, vol. 45, N 15, pp. 3109-3111.
E.Lukevics, L.Ignatovich, S.Belyakov. Crystallographic report: 2-furfurylgermatrane. – Appl. Organomet. Chem., 2004, vol. 18, N 4, p. 203.
G. Veinberg, I. Shestakova, M. Vorona, I. Kanepe, E. Lukevics. Synthesis of antitumor 6-alkylidenepenicillanate sulfones and related 3-alkylidene-2-azetidinones. – Bioorg. Med. Chem. Letters, 2004, vol. 14, No 1, 147-150.
E.Lukevics, L.Ignatovich, T.Shulga, S.Belyakov. 1-[4-(2-Thienyl)phenyl]germatrane. – Appl. Organomet. Chem., 2005, vol. 19, N 1, pp. 167-168.
E.Lukevics, L.Ignatovich. Biological activity of organosilicon compounds. – In: Metallotherapeutic Drugs and Metal-Based Diagnostic Agents. The Use of Metals in Medicine / Eds. M.Gielen, E.R.T.Tiekink/, 2005, J.Wiley & Sons, Ltd. Chichester, pp. 83-107.
E.Lukevics, L.Ignatovich. Biological activity of organogermanium compounds. – In: Metallotherapeutic Drugs and Metal-Based Diagnostic Agents. The Use of Metals in Medicine / Eds. M.Gielen, E.R.T.Tiekink/, 2005, J.Wiley & Sons, Ltd. Chichester, pp. 279-295.
Yu.Melnik, M.Vorona, G.Veinberg, J.Popelis, L.Ignatovich, E.Lukevics. Synthesis and stereoisomerization of 2-(1-alkoxyimino-2,2,2-trifluoroethyl)-5-trimethylsilylfurans. – Chem. Heterocycl. Comp., 2005, vol. 41, N 6, pp. 718-721.
L.Ignatovich, J.Popelis, E.Lukevics. Synthesis and NMR spectra of diaryl- and dihetarylsilacycloalkanes. – In: Organosilicon Chemistry VI / Eds. N.Auner and J.Weis/, Wiley-VCH Weinheim, 2005, vol. 1, pp. 559-562.
L.Ignatovich, D.Zarina, I.Shestakova, S.Germane, E.Lukevics. Synthesis and bological activity of silicon derivatives of 2-trifluoroacetylfuran and their oximes. – In: Organosilicon Chemistry VI / Eds. N.Auner and J.Weis/, Wiley-VCH Weinheim, 2005, vol. 1, pp. 563-568.
E.Lukevics, L.Ignatovich, I.Sleiksha, I.Shestakova, I.Domrachova, J.Popelis. Synthesis and cytotoxic activity of silacycloalkylsubstituted heterocyclic aldehydes. – Appl. Organomet. Chem., 2005, vol. 19, N 10, pp. 1109-1113.
S.Belyakov, E.Alksnis, V.Muravenko, I.Turovskis, J.Popelis, E.Lukevics. Crystal structure and conformation of 8-(2-hydroxyethylamino)- and 8-(pyrrolidin-1-yl)adenosines. – Nucleosides, Nucleotides & Nucleic Acid, 2005, vol. 24, N 8, pp. 1199-1208.
A. Zablotskaya, I.Segal, S.Belyakov, E.Lukevics. Silyl modification of biologically active compounds. 11. Synthesis, physico-chemical and biological evaluation of N-(trialkoxysilylalkyl)tetrahydro(iso,silaiso)quinoline derivatives. Appl. Organomet. Chem. 2006, vol.20, N 2, 149-159.
A.Zablotskaya, I.Segal, J.Popelis, E.Lukevics, S.Baluja, I.Shestakova, I.Domracheva. Silyl modification of biologically active compounds. 12. Silyl group as true incentive to antitumour and antibacterial action of choline and colamine analogues. – Appl. Organomet. Chem. 2006, vol. 20, N 11, 721-728.
E.Lukevics, L.Ignatovich, I.Sleiksha, V.Muravenko, I.Shestakova, S.Belyakov, J.Popelis. Synthesis, structure and cytotoxic activity of 2-acetyl-5-trimethylsilylthiophene(furan) and their oximes. – Appl. Organomet. Chem. 2006, vol 20, N 7, 454-458.
L.Ignatovich, V.Muravenko, S.Grinberga, E.Lukevics. Novel reactions to form an Si-O-Ge group. – Chem.Heterocycl. Comp., 2006, vol. 42, N 2, 268-271.
E.Lukevics, I.Shestakova, I.Domrachova, A.Nesterova, Y.Ashaks, D.Zaruma. Synthesis of complex compounds of methyl derivatives of 8-quinolineselenol with metals and their cytotoxic activity. – Chem.Heterocycl. Comp., 2006, vol. 42, N 1, 53-59.
E.Lukevics, L.Ignatovich, I.Sleiksha, V.Romanov, S.Grinberga, J.Popelis, I.Shestakova. A New method for the synthesis of silicon- and germanium-containing 2-acetylfurans and 2-acetylthiophenes. –Chem.Heterocycl. Comp., 2007, vol. 43, N 2, 143-150.
V.Dirnens, I.Skrastina, J.Popelis, E.Lukevics. Synthesis of isoxazolinylxanthines. – Chem.Heterocycl. Comp., 2007, vol. 43, N 2, 193-196.
E.Lukevics, L.Ignatovich, S.Belyakov. Disordering in the crystal structure of thienylgermatranes. – Chem.Heterocycl. Comp., 2007, vol. 43, N 2, 243-249.
E.Lukevics, I.Shestakova, I.Domrachova, E. Yashchenko, D.Zaruma. Y.Ashaks. Cytotoxic di(8-quinolyl)disulfides. – Chem.Heterocycl. Comp., 2007, vol. 43, N 5, 629-633.
V.M.Vorona, I.Potorocina, G.Veinberg, I.Shestakova, I.Kanepe, M.Petrova, E. Liepinsh, E.Lukevics. Synthesis and structural modification of tert-butyl ester of 7a-chloro-2-(N,N-dimethylaminomethylene)-3-methyl-1,1-dioxoceph-3-em carboxylic acid.- Chem.Heterocycl. Comp., 2007, vol. 43, N 5, 646-652.
A.Zablotskaya, I.Segal, E.Lukevics, S.Belyakov, H.Spies. Tetrahydroquinoline and tetrahydroisoquinoline mixed ligand rhenium complexes with the SNS/S donor atom set.- Appl.Organomet.Chem.,2007, vol.21, N 4, 288-293.
A.Zablotskaya, I.Segal, M. Maiorov, D. Zablotsky, A. Mishnev E.Lukevics, I.Shestakova, I. Domracheva. Synthesis and characterization of nanoparticles with an iron oxide magnetic core and a biologically active trialkylsilylated aliphatic alkanolamine shell. J. Magn. Magn. Mater. 2007, 311, pp. 135-139.
Zablotskaya A., Segal I., Lukevics E., Maiorov M., Zablotsky D., Blums E., Shestakova I., Domracheva I. Synyhesis, physico-chemical and biological study of trialkylsiloxyalkylamine coated iron oxide/oleic acid magnetic nanoparticles for the treatment of cancer. – Appl. Organomet. Chem. 2008, vol. 22, pp. 82-88.
E.Lukevics, E.Abele. Four-membered rings with three heteroatoms not including oxygen, sulfur or nitrogen atom. – In: Comprehensive Heterocyclic Chemistry III., 2008, 2. Four-membered heterocycles together with all fused systems containing a four-membered heterocyclic ring (Exec. Ed. A. Katritzky, FRS: Eds Ch.A. Ramsden, E.V.Scriven, R.J.Taylor), pp. 973-989.
Soualami S., Ignatovich L., Lukevics E.,Ourari A., Jouikov V. Electrochemical oxidation of benzylgermatranes. – J. Organomet. Chem., 2008, vol.693 (7), pp. 1346-1352.
Lukevics E., Ignatovich L., Shul’ga T., Belyakov S. Synthesis and crystal structure of 1-(4-fluorophenyl)- and 1-(4-dimethylamino)phenylgermatranes. – Chem. Heterocycl.Comp. (Engl.Ed.), 2008, vol. 44 (5), pp. 615-620.
Abele E., Lukevics E. Synthesis of Heterocycles from Oximes. – In: The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids. (Eds. Z.Rapoport, J.F.Liebmann ), J.Wiley, Chichester, 2009, Part I, pp. 233-302.
Erchak N., Belyakov S., Kalvinsh I., Pypowski K., Valbahs E., Lukevics E. Two polymorphic modifications of 1-(N-morpholiniomethyl)spirobi(3-oxo-2,5-dioxa-1-silacyclopentan)ate hydrate. –Chem.Heterocycl. Comp.(Engl. Ed.), 2009, vol. 45, N 9, pp.1137-1143..
Zablotskaya A.,Segal I., Lukevics E., Maiorov M., Zablotsky D., Blums E., Shestakova I., Domracheva I. Water-soluble magnetic nanoparticleswith biologically active stabilizers. – J.Magn.Mater.,2009, 321, pp. 1428-1432.
Ignatovich L., Muravenko V., Shestakova I., Domracheva I, Popelis J., Lukevics E. Synthesis and Cytotoxic activity of new 2-[(3-aminopropyl)- dimethylsilyl]-5-triethylsilylfurans. – Appl. Organomet. Chem. 2009, DOI 10.1002, aoc, 1538.
Vorona M., Veinberg G.,Liepinsh E., Kazoka H., Andrejeva G., Lukevics E. Enzymatic synthesis of amoxycilloic acids. – Chem.Heterocycl. Comp.(Engl. Ed.), 2009, vol. 45, N 6, pp.782-754.
Zablotskaya A.,Segal I., Lukevics E. Iron oxide-based magnetic nanostructures bearing cytotoxic organosilicon molecules for drug delivery and therapy. – Appl. Organomet. Chem. 2010, vol. 24, N 3, pp. 150-157.
Ignatovich L., Muravenko V., Shestakova I., Domracheva I, Popelis J., Lukevics E. Synthesis and Cytotoxic activity of new 2-[(3-aminopropyl)- dimethylsilyl]-5-triethylsilylfurans. – Appl. Organomet. Chem. 2010, vol. 24, N 3, pp. 158-161.
Segal I., Zablotskaya A.,Lukevics E., Maiorov M., Zablotsky D., Blums E., Mishnew A., Georgieva R., Shestakova I., Gulbe A. Preparation and cytotoxic properties of goethite-based nanoparticles covered with decyldimethyl(dimethylaminoethoxy)silane metoxyde. – Appl. Organomet. Chem. 2010, vol. 24, N 3, pp. 193-197.
Ignatovich L., Muravenko V., RomanovsV, Sleiksha I., Shestakova I., Domracheva I, Belyakov S., Popelis J., Lukevics E. Synthesis, structure and cytotoxic activity of new 1-[5-organylsilyl(germyl)-2-furyl(thienyl)]nitroethenes. – Appl. Organomet. Chem. 2010, vol. 24, N 12, pp. 858-864.
Lukevics E., Abele E., Ignatovich L. Biologically Active Silacyclanes. – Adv. Heterocycl. Chem., 2010, vol. 99, pp. 107-141.
Abele E., Lukevics E. Synthesis, structure and reactions of organometallic derivatives of oximes. – In: The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids. Eds. by Zvi Rapoport, J.F.Liebman. 2011, Vol.2, Part 1 (Chapter 4), pp. 145-203.
Katkevics M., Kukosha T., Lukevics E. Heterocycles from hydroxylamines and hydroxamic acids. – In: The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids. Eds. by Zvi Rapoport, J.F.Liebman. 2011, Vol.2, Part 1 (Chapter 5), pp. 205-293.

Research Projects:

E.Lukevics (Head of Project). Silylheterocycles in Organic Chemistry. Latvian Council of Science (1993-1995).
E.Lukevics (Head of Project). Bifunctional Organosilicon Compounds. Latvian Council of Science (1993-1995).
E.Lukevics (Head of Project). Synthesis of Heterocyclic Organosilicon and Organogermanium Compounds, Investigation of their Physical and Chemical Properties. Latvian Council of Science (1997-2000 ).
E.Lukevics (Head of Project). Asymmetric and Catalytic Synthesis of Heteroaromatic Compounds. Latvian Council of Science (1997-2000 ).
E.Lukevics (Head of Program). The Development of Modern Methods of Organic Chemistry Directed towards the Development of Pharmaceutical Industry in Latvia. Latvian Council of Science (1997-2000 ).
E.Lukevics (Head of Project). Experimental and Theoretical Aspects of the Catalytical Synthesis of Heteroaromatic Compounds. Latvian Council of Science (2001 –2004 ).
E.Lukevics (Head of Project). Comparative Study of the Structure and Biological Activity of Organosilicon and Organogermanium Compounds. Latvian Council of Science (2001 – 2004).
E.Lukevics (Head of Project). Heterocyclic Derivatives of Tetra- and Hypercoordinated Germanium and Silicon. Latvian Council of Science (2005 -).
E.Lukevics ( Programme Director). Development of Organic Synthesis Methods for Obtaining of Biologically Active Compounds. Latvian Council of Science (2002 -2005 ).
E.Lukevics ( Programme Director). Development of Heteroatom Chemistry for Preparation of Biologically Active Compounds. Latvian Council of Science (2006 – 2009 ).
E.Lukevics (Head of Project). Carbofunctional Silylheterocycles. Latvian Council of Science (2009 ).

Hobbies:

Opera, Basketball, Mountains.

Edmunds LUKEVICS

Edmunds LUKEVICS
Head of Laboratory of Organometallic Chemistry

Latvian Institute of Organic Synthesis

Aizkraukles iela 21,
Riga, LV-1006
http://www.lza.lv/scientists/lukevics.htm

Born: December 14, 1936, Liepaja, Latvia
Departed: November 21, 2009, Riga, Latvia

Interests in inventing:

Development of medicament synthesis and technology
Development of the synthesis and technology of agricultural chemicals

Main invention:

In the sphere of medicament synthesis:

Acylete derivatives of aminobenzylpenicillin with antimicrobe activity.
Co-authors: G.Veinbergs, G.Kvitsors a.o.
Authors’ certificate of USSR Nr.1829360, 1992
Substituted 3-hydrazinopropionates and their pharmaceutically available salts with antiarythmic activity.
Co-authors: G.Bremanis, I. Kalvins, I.Ancena a.o.
Authors’ certificate of USSR Nr.1247012, 1986.
Patent of USA Nr. 4633014
Patent of England Nr. 2144121
Patent of France Nr. 2549050
Patent of Italy Nr.1175577

In the sphere of the synthesis of agricultural chemicals:

2,2 –dimethyl-6-alkyl–1,3-dioxa-6-aza-2-silacyclooctanes with antiinsect activity.
Co-authors: V.Markina, N.Smirnova a.o.
Authors’ certificate of USSR Nr.687855, 1978.
Lucerne productivity stimulator.
Co-authors: L.Sermans, V.Janisevska, G.Zelcans a.o.
Authors’ certificate of USSR Nr. 1161056, 1985

Selection of patent documents:

Totally: 104 authors’ certificates of USSR, 11 patents of Latvia, 3 patents of Germany, 3 patents of Canada, 3 patents of France, 3 patents of Italy, 1 patent of Japan, 1 patent of Switzerland, 4 patents of Great Britain, 5 patents of USA.

Patents of Latvia:

E.Lukevics, D.Feldmane, H.Kazoka, I.Turovskis. Method for obtaining metoxi-alpha-methylbenzyl alcohol. Patent of Latvia Nr. 11864, C 07 C 29/58, 1997;
E.Lukevics, V.Slavinska, Dz.Sile, M.Katkevics, E.Korcagova. Method for obtaining 2-oxo-4-phenylbutane acid ethylester. Patent of Latvia Nr. 11891, C 07 C 69/716, 1998;
E.Lukevics, V.Slavinska, Dz.Sile, M.Katkevics, E.Korcagova, V.Belikovs. Method for obtaining 2-oxo-4-phenylbutane acid ethylester. Patent of Latvia Nr. 11892, C 07 C 69/716, 1998;
E.Lukevics, I.Kalvins, A.Birmans. Cardioprotector “Mildronate”. Patent of Latvia Nr. 5402, A 61 K 31/205, 1994;
E.Lukevics, G.Veinbergs, I.Sestakova, I.Kalvins. Cephalosporin derivatives with citostatic activity. Patent of Latvia Nr. 11953, C 07 D 501/02, 1998.