Jacek Morzycki
Full Professor
Jacek W. Morzycki (head),
phone: (+48) (85) 745-75-85,
Ph.D. 1977, D.Sc. 1986,Professor 1998

15-443 Białystok, al. J. Piłsudskiego 11/4


Stanisław Witkowski, Ph.D. 1987, phone: (+48) (85) 745-75-86,
Zenon Łotowski, Ph.D. 1995, phone: (+48) (85) 745-76-04,
Agnieszka Z. Wilczewska, Ph.D. 1998, phone: (+48) (85) 745-75-88,
Leszek Siergiejczyk, Ph.D., 1999, phone: (+48) (85) 745-75-76,
Agnieszka Wojtkielewicz, Ph.D. 2002, phone: (+48) (85) 745-76-04,
Izabella Jastrzębska, M.Sc., phone: (+48) (85) 745-75-88,
Piotr Wałejko, Ph.D., phone: (+48) (85) 745-75-86.

Technical research assistants:
Barbara Lachowska, M.Sc., phone: (+48) (85) 745-75-76,
Jadwiga Maj, M.Sc. phone: (+48) (85) 745-75-95.
RESEARCH INTEREST
Design and development of new strategies for the synthesis of biologically active natural products and their analogs. Partial synthesis of aza analogs of steroid hormones, vitamin D, cholesterol etc. Design and synthesis of 5alpha-reductase inhibitors. Chemical and spectral properties of steroidal enamides. Heterocyclic chemistry; biologically active 1-(2-pyrimidyl)piperazine derivatives. Synthesis of some dimeric steroids, as components of artificial lipid bilayer membranes. Dimeric steroid-pyrazine marine alkaloids, bis-steroidal pyrazines, analogs of cephalostatins. Cytotoxic steroidal saponins, cholestane glycosides. Synthesis of a highly potent antitumor natural product OSW-1 and its analogs. Structure determination by spectroscopic methods. Vitamin E studies including some new reactions of alpha-tocopherol, synthesis of new derivatives of alpha-tocopherol (e.g. glycosides) with increased amphiphylic properties and better permeability through biological membranes. Conformational analysis of chroman skeleton by dynamic NMR and other techniques. Synthesis and structural investigations of alpha-tocopherol derivatives (NMR in solution and solid state). Chiral pesticides. Development of new methods for determination of selected pesticide residues.

PUBLICATIONS

Bavouzet B., Destarac M., Herve P., Wilczewska A. Z. 2003. Cosmetic composition comprising a block copolymer. Patent docket No. DRN01046.

Cadena N., Herve P., Destarac M., Wilczewska A. Z. 2003. Method for depositing polymer onto a surface by applying a composition onto said surface. Patent docket No. DRN01045.

Gryszkiewicz-Wojtkielewicz A., Jastrzębska I., Morzycki J. W., Romanowska D. B. 2003. Approaches towards the synthesis of cephalostatins, ritterazines and saponins from Ornithogalum saundersiae – new natural products with cytostatic activity. Current Organic Chemistry 7: 1-22.

Herve P., Destarac M., Anthony O., Bavouzet B., Joanicot M., Wilczewska A. Z. 2003. Formulation comprising an ionic compound, a polyionic polymer, and a block copolymer. Patent docket No. DRN01044.

Anulewicz-Ostrowska R., Jastrzębska I., Morzycki J. W., Wójcik J. 2002. An assisted solvolysis of 23-spirostanyl bromides and tosylates. A new rearrangement of spirostanes to the bisfuran systems. J. Org. Chem. 67: 6916-6924.

Destarac M.,  Brochon C., Catala J-M., Wilczewska A. Z., Zard S. Z. 2002. Macromolecular design via the interchange of xanthates (MADIX). Polymerization of styrene with O‑ethyl xanthates as controlling agents. Macromol. Chem. Phys. 203: 2281-2289.

Jastrzębska I., Katryński K. S., Morzycki J. W. 2002. Further study on oxidation of pseudosapogenins. Arkivoc IX: 46-54.

Kroszczyński W., Morzycka B., Morzycki J. W. 2002. Nie kończąca się historia witaminy D. Wiadomości Chemiczne 56: 793-809.

Krysiński P., Żebrowska A., Pałys B., Łotowski Z. 2002. Spectroscopic and electrochemical studies of bilayer lipid membranes tethered to the surface of gold. Journal of the Electrochemical Society 149: 189-194.

Łotowski Z., Morzycki J. W., Niewczas I. S., Zdanowicz M. 2002. Synthesis of cis and trans isomers of D-ring linked bis-steroid pyrazines from 16alpha-bromo-17-oxosteroids. Collect. Czech. Chem. Commun. 67: 47-54.

Morzycki J. W., Wawer I., Gryszkiewicz A., Maj J., Siergiejczyk L., Zaworska A. 2002. 13C‑NMR study of 4-azasteroids in solution and solid state. Steroids 67: 621-626.        

Morzycki J. W., Wojtkielewicz A. 2002. Synthesis of a cholestane glycoside OSW-1 with potent cytostatic activity. Carbohydrate Research 337: 1269-1274.

Witkowski S. 2002. Działanie destrukcyjne wolnych rodników na błony komórkowe. Rola ochronna witaminy E. Farmacja Polska 56: 922-28.

Witkowski S., Knaś M., Wałejko P., Zwierz K., Dudzik D. 2002. Badanie szybkości rozpadu glikozydów alfa-tokoferolu w homogenatach tkanek szczura. Farmacja Polska 56: 977-8.

Witkowski S., Wałejko P. 2002. Studies in the acid catalysed glycosylation of alpha-tocopherol. Z. Naturforsch., 57b: 571-78.

Witkowski S., Wałejko P., Jóźwik M. 2002. Badanie wpływu rozpuszczalników na peroksydację lipidów w homogenacie mózgu wołowego. Farmacja Polska 56: 979-80.

Witkowski S., Wawer I. 2002. 13C NMR Studies of conformational dynamics in alpha-tocopherol esters in solution and solid state. J. Chem. Soc., Perkin Trans. 2: 433-436.

Tarasów E., Siergiejczyk L., Panasiuk A., Kubas B., Prokopowicz D., Walecki J. 2002. Zastosowanie spektroskopii protonowej MR do badań wątroby  in vivo u osób zdrowych. Med. Sci. Monit. 8: 36-40.

Żebrowska A., Krysiński P., Łotowski Z. 2002. Electrochemical studies of blocking properties of solid supported tethered lipid membranes on gold. Bioelectrochemistry 56: 179-184.

Łotowski Z., Maj J., Morzycki J. W. 2001. 3-Bromomethylcholest-2-ene and its reactions. Chem. Papers 55: 118-120.

Morzycki J. W., Gryszkiewicz A. 2001. Synthesis of the potent antitumor saponin OSW-1 aglycone. Polish J. Chem. 75: 983-989.

Morzycki J. W., Gryszkiewicz A., Jastrzębska I. 2001. Neighboring group participation in epoxide ring cleavage in reactions of some 16alpha,17alpha-oxidosteroids with lithium hydroperoxide, Tetrahedron 57: 2185-2193.

Morzycki J. W., Jastrzębska I. 2001. Novel transformation of  23-bromosapogenins. Synthesis of  (22S,23R)-22-hydroxy-23,26-epoxyfurostanes. Tetrahedron Letters 42: 5989-5991.

Morzycki J. W., Maj J., Nikitiuk A., Kwolek G., Malinowska B. 2001. Three new derivatives of 3-amino-1,2-propanediol; their spectral properties and biological evaluation. Acta Poloniae Pharmaceutica 58: 249-256.

Taton D., Wilczewska, A. Z. Destarac M. 2001. Direct synthesis of double hydrophilic statistical di- and triblock copolymers comprised of acrylamide and acrylic acid units via the MADIX process. Macromol. Rapid Commun. 22: 1497-1503.

Wałejko P., Żołek T., Witkowski S., Wawer I. 2001. Investigation of conformational effects in glycosides of alpha-tocopherol derivatives by means of NMR spectroscopy and Molecular Modelling. Molecular Physics Reports 33: 70-73.

Wawer I., Witkowski S. 2001. Analysis of solid state 13C NMR spectra of biologically active compounds, Curr. Org. Chem. 5: 191-203.

Witkowski S. 2001. Strukturalne aspekty aktywności biologicznej witaminy E. Farmacja Polska 57: 714-718.

Witkowski S., Anulewicz-Ostrowska R., Krygowski T. M. 2001. Water molecules as a gluing factor in organic crystals. Part 2. Crystal and molecular structure of 6-acetoxy-2,5,7,8-tetramethylchroman-2-carboxylic acid monohydrate. Pol. J Chem. 75: 883-888.

Witkowski S., Wałejko P. 2001. Synthesis of alpha-tocopheryl glycosides. Z. Naturforsch. 56b: 411-415.

Witkowski S., Wawer I. 2001. Cross-polarisation MAS 13C NMR in 2,2,5,7,8-pentamethylchroman-6-ol, alpha-tocopherol model compound. Molecular Physics Reports 33: 74-77.

Wilczewska A., Destarac M., Zard S. Z., Kalai Ch., Mignani G. Procédé de réduction radicaler de fonctions dithiocarbonylées ou dithiophosporylées portées par un polymère. Zgłoszenie patentowe RHODIA CHIMIE  France 01,  11496 (05.09.2001).

Wilczewska A., Destarac M., Zard S. Z., Kalai Ch., Mignani G. Procédé de synthèse de polymères a functions thiols. Zgłoszenie patentowe RHODIA CHIMIE France 01, 11494 (05.09.2001).

Kalinowski S., Łotowski Z., Morzycki J. W. 2000. The influence of bolaamphiphilic steroid dimer on the formation and structure of bilayer lipid membranes. Cellular & Molecular Biology Letters 5: 107-128.

Łotowski Z., Dubis E. N., Morzycki J. W. 2000. Functionalization of dimeric cholestanopyrazines at the quasi-benzylic position. Monatsh. Chem. 131: 65-71.

Morzycki J. W., Gryszkiewicz A., Chilmonczyk Z., Cybulski J., Szelejewski W. Sposób otrzymywania pochodnych 16alfa,17beta-dihydroksy-steroidowych do syntez saponin OSW. Zgłoszenie patentowe P-338496 (18.02.2000).

Morzycki J. W., Gryszkiewicz A., Jastrzębska I. 2000. Some reactions of 16alpha,17alpha-oxido-steroids: a study related to the synthesis of the potent anti-tumor saponin OSW-1 aglycone. Tetrahedron Letters 41: 3751-3754.

Popławski J., Łozowicka B., Dubis A. T., Lachowska B., Witkowski S., Siluk D., Petrusewicz J., Kaliszan R., Cybulski J., Chilmonczyk Z. 2000. Synthesis and hypolipidemic antiplatelet activities of alpha-asarone isomers in humans (in vitro), mice (in vivo), and rats (in vivo). J. Med. Chem. 43: 3671-3676.

Siergiejczyk L., Popławski J., Łozowicka B., Dubis A., Lachowska B. 2000. 1H and 13C NMR spectral analysis of (E)-asarone and its isomers, Magn. Reson. Chem., 38: 1037-1038.

Wałejko P., Witkowski S., Wawer I., Szczepanik T. 2000. 1H and 13C NMR studies of vitamin E glycosides stereochemistry,  Mol. Phys. Rep. 29: 192-194.

Witkowski S., Maciejewska D., Wawer I. 2000. 13C NMR studies of conformational dynamics in 2,2,5,7,8-pentamethylchroman-6-ol derivatives in solution and the solid state. J. Chem. Soc., Perkin Trans. 2: 1471-1776.

Quiclet-Sire B., Wilczewska A. Z., Zard S. Z. 2000. A practical process for polymer-supported synthesis. Tetrahedron Lett. 41: 5673-5677.

Dubis E. N., Dubis A. T., Morzycki J. W. 1999. Comparative analysis of plant cuticular waxes using HATR FT-IR reflection technique. Journal of Molecule Structure: 173-179.

Koronkiewicz S., Bryl K., Witkowski S., Wałejko P. 1999. Changes of structural and dynamic properties of model lipid membranes induced by tocopherols. Natural Sciences: 19-33.

Łotowski Z., Gryszkiewicz A., Borowiecka J. B., Nikitiuk A., Morzycki J. W. 1999. A facile synthesis of symmetrical dimeric steroid-pyrazines. J. Chem. Research (S): 662-663.

Morzycki J. W., Chilmonczyk Z., Cybulski J., Zaworska A., Szelejewski W., Dzikowska J. Sposób otrzymywania 17-podstawionych pochodnych 3-okso-4-aza-5-androstanu. Patent PL 177095 B1 (30.09.1999).

Dubis A. T., Łotowski Z., Siergiejczyk L., Wilczewska A. Z., Morzycki J. W. 1998. Study of hydrogen bonding in nitro enamides. J. Chem. Research (S): 170-171; (M): 813-821.

Grzegorzewski P., Koladkiewicz I., Morzycki J. W., Sicinski R. R. 1998. Synthesis and photochemical transformations of 19-phenylsulfonyl provitamin D analogue. Collect. Czech. Chem. Commun. 63: 1597-1612.

Łotowski Z., Morzycki J. W. 1998. Preparation of 7alpha- and 7beta-methylcholestane derivatives by kinetic separation of the diastereomeric mixture. Tetrahedron: Asymmetry 9: 1627-1633.

Morzycki J. W., Gryszkiewicz A., Łotowski Z., Szczepek W. J. 1998. Reduction of 2-nitro-5alpha-cholestan-3-one, its enol tautomer and 2-nitro-5alpha-cholest-2-en-3-amine derivatives. Synthesis of bis-steroidal pyrazines. Collect. Czech. Chem. Commun. 63: 1589-1596.

Witkowski S., Wałejko P. 1998. Bromination of alpha-tocopherol acetate. Bull. Pol. Acad. Sci. 46: 349-352.

Witkowski S., Wałejko P., Wawer I. 1998. 13C CP MAS NMR study of 6-O-(beta-D-glucopyranosyl)- and 6-O-(beta-D-mannopyranosyl)-d-alpha-tocopherols. Solid State Nuclear Magnetic Resonance 10: 123-128.

Plesnar Z., Malanowski S., Łotowski Z., Morzycki J. W., Frelek J., Wójcik J. 1997. Stereospecific association of C-20 epimers of  3beta-hydroxy-16-oxo-24-nor-17-azachol-5-eno-23-nitrile. Z. Naturforsch. 52b: 749-756.

Morzycki J. W., Kalinowski S., Łotowski Z., Rabiczko J. 1997. Synthesis of dimeric steroids as components of lipid membranes. Tetrahedron 53: 10579-10590.

Morzycki J. W., Łotowski Z., Stępniowska M., Gryszkiewicz A., Wilczewska A. Z. 1997. Nitration of N-acetyl enamines with acetyl nitrate. Tetrahedron 53: 16161-16168.

Morzycki J. W., Wilczewska A. Z. 1997. Electrophilic reactions of 4-methyl-A-homo-4-azacholest-4a-en-3-one. Tetrahedron 53: 10565-10578.

Witkowski S., Markowska A., Wałejko P. 1997. Preparation and reactions of 5-nitromethyl-g-tocopheryl acetate. Pol. J. Chem. 71: 449-453.

Morzycki J. W., Dąbrowski Z., Trusewicz M., Wilczewska A. Z. 1996. Unusual oxidation reactions of 7alpha-methyl- and 7alpha-phenylcholest-5-ene-3beta,7beta-diol. Monatsh. Chem. 127: 1283-1289.

Morzycki J. W., Łotowski Z., Wilczewska A. Z., Stuart J. D. 1996. Synthesis of 4,17-diazasteroid inhibitors of human 5alpha)-reductase. Bioorganic & Medicinal Chemistry 4: 1209-1215.

Morzycki J. W., Wilczewska A. Z. 1996. Reactions of 4-azacholest-5-en-3-one, 6-azacholest-4-en-7-one, and their N-methyl derivatives with electrophilic reagents. Tetrahedron 52:14057-14067.

Morzycki J. W., Wilczewska A. Z., Łotowski Z. 1996. On reaction of enamides with acetyl nitrate. Tetrahedron Lett. 37: 2079-2082.

Witkowski S., Popławski J. 1996. Oxidation of alpha-tocopherol with dioxane dibromide. Pol. J. Chem. 70: 1448-1452.

Witkowski S., Markowska A. 1996. Nitration of alpha-tocopherol acetate. Pol. J. Chem. 70: 656-657.

Morzycki J. W. 1995. Partial synthesis of azasteroids. Praca przeglądowa. Polish J. Chem. 69: 321-340.

Morzycki J. W., Łotowski Z. 1995. Studies on the construction of the 2-isooctyl side chain in 17-azasteroids. Monatsh. Chem. 126: 119-128.

 Morzycki J. W., Łotowski Z. 1995. Synthesis of 17-azacholesterol. Heterocycles 41: 931-936.

Morzycki J. W., Łotowski Z., Siergiejczyk L., Lipkowski J., Tabaszewska A., Wójcik J. 1995. Structure of 3beta-hydroxy-16-oxo-24-nor-17-azachol-5-eno-23-nitrile and its 20S

Epimer. Steroids 60: 195-203.

Morzycki J. W., Wilczewska A. Z., Żochowska E., Łotowski Z. 1995. Stereoselective reduction of the double bond in delta5-3-oxo-4-azasteroids. Heterocycles 41: 2729-2736.

Back T. G., Baron D. L., Morzycki J. W. 1994. Preparation of 6-azaandrost-4-ene-3,7,17-trione and some related 3-oxygenated 6-azaandrostanes. Heterocycles 38: 1053-1060.

Morzycki J. W., Łotowski Z. 1994. N-Alkylation of 17-azasteroids. Steroids 59: 30-33.

Morzycki J. W., Krupska A., Sołowiej M. 1993. Reakcje octanu 7-oksocholesterolu z odczynnikami Grignarda. Badania nad syntezą pochodnych prowitaminy D3 podstawionych w pozycji 7. Zeszyty FUW 74: tom XI, 25-39.

Morzycki J. W., Obidzińska J. 1993. Reakcja retroaldolowa  w układzie 3beta,6beta-diacetoksy-5beta-metylo-9,10‑secocholestano-9,10-dionu. Zeszyty FUW 74: tom XI, 5-23.

Popławski J., Lux S., Witkowski S., Dubis E., Dubis A., Wróbel J. T., Dmoch J. 1993. Preliminary Isolation Study of the Colorado Beetle Leptinotarsa Decemlineata Say Body Components and Their Influence on the Male Behaviour. Bull. Pol. Acad. Sci. 41: 243-248.

Popławski J., Różański A., Siergiejczyk L. 1993. Determination of anomeric configuration of 3-acetyl-5-[2-(3,4-dihydroxytetrahydrofuryl)]-2-methylpyrrole by NMR spectroscopy based on the spectral analysis of a single isomer. Bull. Pol. Ac. Sci., Chem. 41/4: 195-203.

Back T. G., Chau J. H.-L., Codding P. W., Gladstone P. L., Jones D. H., Morzycki J. W., Roszak A. W. 1992. A novel stereospecific rearrangement of 3-substituted B-homo 5-azasteroids to their A-nor analogs. Preparation, stereochemistry and conformational studies. J. Org. Chem. 57: 4110-4121.

Morzycki J. W., Benedysiuk A., Łaźny R. 1992. Reactions of beta-keto ester enol ethers with 3‑chloro-peroxybenzoic acid. Polish J. Chem. 66: 1191-1193.

Witkowski S., Rao Y. K., Premchandran R. H., Halushka P. V., Fried J. 1992. Total synthesis of (+)-10,10-difluorothromboxane A2 and its 9,11 and 15 stereoisomers. J. Am. Chem. Soc. 114: 8464-72.


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