Research

 

Main research interests

1. Synthesis, structure determination of azaphenothiazines and evaluation of their biological activities.

2. Synthesis, structure determination and evaluation of anticancer activity for new derivatives of betulin.

3. Synthesis of new sulfur derivatives of azines: quinoline, pyridine and purine, and evaluation of their pharmacological activities.

 

Research techniques

1. Synthesis, isolation and identification of organic compounds.

2. Application of NMR (1H, 13C, 14N, 15N, one- and two-dimensional) and IR spectroscopy, MS and HRMS spectrometry, and single-crystal X-ray diffraction in the structural analysis of organic compounds.

3. Identification and separation with use of chromatography TLC, LC and flash.

4. Application of electrochemical and microwave techniques and pressure reactors in organic synthesis.

5. Molecular modeling of organic compounds.

6. Correlation of physical, chemical and biological properties of organic chemistry.

 

Selected papers of the last 5 years

1. K. Marciniec, A. Maślankiewicz, „From 2,3-, 2,6-, 3,4- and 4,6-dichloroquinolines to isomeric chloroquinolinesulfonyl chlorides”, Heterocycles, 81, 305-316 (2010).

2. K. Pluta, M. Jeleń, B. Morak-Młodawska, M. Zimecki, J. Artym, M. Kocięba – “Anticancer activity of newly synthesized azaphenothiazines in NCI’s anticancer screening”, Pharmacol. Reports, 62, 319-332 (2010).

3. B. Morak-Młodawska, K. Pluta, A.N. Matralis, A.P. Kourounakis – “Antioxidant activity of newly synthesized 2,7-diazaphenothiazines”, Archiv. Pharm. Chem. Life Sci. 343, 268-273 (2010).

4. B. Morak-Młodawska, K. Pluta, K. Suwińska, M. Jeleń – „Alkylations of 10H-2,7-diaza-phenothiazine to alkyl-2,7-diazaphenothiazinium salts and 7-alkyl-2,7-diazapheno-thiazines, Heterocycles, 81, 2511-2522 (2010).

5. E. Chrobak, M. Wlekliński, A. Maślankiewicz, J. Kusz, M. Zubko, A. Zięba, „2-Methyl- and 2-dimetylaminoquino[4,3-e]-1,2,4-thiadiazine 4,4-dioxides – synthesis, structure and N-methylation”, Heterocycles, 81, 1799-1810 (2010)

6. S. Boryczka, M. Jastrzębska, M. Nowak, J. Kusz, R. Wrzalik, J. Wietrzyk, M. Matyja, „Synthesis, X-ray structure and antiproliferative activity of 3-benzylthio-4-propargylselenoquinoline”, Med. Chem. Res., 19, 551-564 (2010).

7. A. Zięba, A. Sochanik, A. Szurko, M. Rams, A. Mrozek, P. Cmoch, “Synthesis and in vitro antiproliferative activity of 5-alkyl-12(H)-quino[3,4-b] [1,4]benzothiazinium salts”, Eur. J. Med. Chem., 45, 4733-4739 (2010).

8. K. Pluta, M. Jeleń, B. Morak-Młodawska, M. Zimecki, J. Artym, M. Kocięba “Anticancer activity of newly synthesized azaphenothiazines in NCI’s anticancer screening”, Pharmacol. Reports, 62, 319-332 (2010).

9. S. Boryczka, M. Mól, M. Milczarek, J. Wietrzyk, E. Bębenek, „Synthesis and in vitro antiproliferative activity of novel (4-chloro-and 4-acyloxy-2-butynyl)thioquinolines”, Med. Chem. Res., 20, 1402-1410 (2011).

10. P. Zajdel, K. Marciniec, A. Maślankiewicz, M.H. Paluchowska, G. Satała, A. Partyka, M. Jastrzębska-Więsek, D. Wróbel, A. Wesołowska, B. Duszyńska, A.J. Bojarski, M. Pawłowski, "Arene- and guinoline-sulfonamides as novel 5-HT7 receptor ligands", Bioorg. Med. Chem., 19, 6750-6759 (2011).

11. L. Skrzypek, A. Maślankiewicz, K. Suwińska, “Synthesis of 3-alkanesulfonyl-4(1H)-quinolinones from 3-alkanesulfonyl-4-alkylsulfanylquinolines”, Heterocycles, 83, 777- 787 (2011).

12. E. Chrobak, M. Wlekliński, A. Maślankiewicz, J. Kusz, M. Zubko, E. Michalik, “Pyrido- and quino-1,2,4-thiadiazine S,S-dioxides from reactions of 4-chloro-3-pyridinesulfonyl- and 4-chloro-3-quinolinesulfonyl chlorides with O-methylisourea”, Heterocycles, 83, 1819-1830, (2011).

13. M. Jeleń, B. Morak-Młodawska, K. Pluta „Thin-layer chromatographic detection of new azaphenothiazines”, J. Pharm. Biomed. Anal., 55, 466-471 (2011).

14. K. Pluta, B. Morak-Młodawska, M. Jeleń “Recent progress in biological activities of synthesized phenothiazines”, Eur. J. Med. Chem., 46, 3179-3189 (2011).

15. P. Zajdel, K. Marciniec, A. Maślankiewicz, G. Satała, B. Duszyńska, A.J. Bojarski, A. Partyka, M. Jastrzębska-Więsek, D. Wróbel, A. Wesołowska, M. Pawłowski, “Quinoline- and isoquinoline-sulfonamide derivatives of LCAP as potent CNS multi-receptor–5-HT1A/5-HT2A/5-HT7 and D2/D3/D4–agents: the synthesis and pharmacological evaluation”, Bioorg. Med. Chem, 20, 1545-1556 (2012).

16. B. Morak-Młodawska, K. Suwińska, K. Pluta, M.Jeleń, „10-(3’-Nitro-4’-pyridyl)-1,8-diazaphenothiazine as the double Smiles rearrangement”, J. Mol. Struct., 1015, 94-98 (2012).

17. K. Marciniec, A. Maślankiewicz, M.J. Maślankiewicz, R. Kurczab, „Synthesis, 15N NMR spectra and GIAO calculated data of the seven positional isomers of 15N-labeled N,N-dimethylsulfamoylquinoline”, J. Mol. Struct., 1015, 46-50 (2012).

18. M. Jeleń, K. Suwińska, C. Besnard, K. Pluta, B. Morak-Młodawska, “The structures of 8- and 10-trifluoromethylquino[3,2-b]benzo[1,4]thiazines and their benzyl derivatives”, Heterocycles, 85, 2281-2290 (2012).

19. A. Kowalska, K. Pluta, „Synthesis of 2- and 6-(dialkylaminoalkylthio)- and 2,6-bis(dialkyl-aminoalkylthio)-7-methylpurines”, Heterocycles, 85, 2473-2483 (2012).

20. S. Boryczka, M. Jastrzębska, E. Bębenek, J. Kusz, M. Zubko, M. Kadela, E. Michalik, “X-Ray diffraction and infrared spectroscopy of N,N-dimethylformamide and dimethyl sulfoxide solvatomorphs of betulonic acid”, J. Pharm. Sci., 101, 4458-4471 (2012).

21. E. Chrobak, A. Maślankiewicz, M .Chyćko, L. Skrzypek, M. Szmielew, M.J. Maślankiewicz, J. Kusz, M. Zubko, “Preparation and oxidative-chlorination splitting of nitro derivatives of 1,4-dithiino[2,3-C:5,6-C′]diquinoline as a source of 4-substituted 5- and 8-nitro-3-quinolinesulfonic acid derivatives”, Phosphorus, Sulfur Silicon Relat. Elem., 187, 1208–1225 (2012).

22. A. Zięba, M. Latocha, A. Sochanik, “Synthesis and in vitro antiproliferative activity of novel 12(H)-quino[3,4-b][1,4]benzothiazine derivatives”, Med. Chem. Res., 22, 4158-4163 (2013).

23. M. Jeleń, K. Pluta, M. Zimecki, B. Morak-Młodawska, J. Artym, M. Kocięba „Synthesis and selected immunological properties of substituted quino[3,2-b]benzo[1,4]thiazines”, Eur. J. Med. Chem. 63, 444-456 (2013).

24. M. Jeleń, K. Pluta, M. Zimecki, B. Morak-Młodawska, J. Artym, M. Kocięba, „6-Substituted 9-fluoroquino[3,2-b]benzo[1,4]thiazines display strong antiproliferative and antitumor properties”, Eur. J. Med. Chem. 89, 411-420 (2015).

25. M. Jastrzębska, S. Boryczka, M. Kadela, R. Wrzalik, J. Kusz, M. Nowak, „Synthesis, crystal structure and infrared spectra of new 6- and 7-propylamine-5,8-quinolinediones”, J. Mol. Struct. 1067, 160-168, 2014.

26. E. Chrobak, E. Michalik, J. Kusz, M. Nowak, S. Boryczka, „Polymorphic forms of lupane triterpenoid betulonic aldehyde (betulonal)”, Acta Cyst. C70, 847-851, 2014.

27. M. Jeleń, K. Pluta, B. Morak-Młodawska, “Determination of the lipophilicity parameters of new antiproliferative 8-10-substituted quinobenzothiazines by computational methods and RP TLC”, J. Liq. Chromatogr. & Rel. Technol., 37, 1373-1382 (2014).

28. B. Morak-Młodawska, K. Pluta, M. Jeleń, „Estimation of the lipophilicity of new anticancer and immunosupressive 1,8-diazaphenothiazines derivatives”, J. Chromatogr. Sci. 53, 462-466 (2015).

29. A. Czarny, E. Zaczyńska, M. Jeleń, M. Zimecki, K. Pluta, B. Morak-Młodawska, J. Artym, M. Kocięba, „Antibacterial properties of substituted quino[3,2-b]benzo[1,4]thiazines”, Polish J. Microb. 63, 335-339 (2014).

30. P. Zajdel, A. Partyka, K. Marciniec, A. J. Bojarski, M. Pawłowski, A. Wesołowska, „Quinoline- and isoquinoline-sulfonamide analogs of aripiprazole: Novel antipsychotic agents?”, Future Med. Chem., 6, 57-75 (2014).

31. K. Marciniec, M. Latocha, S. Boryczka, R.,„Synthesis, molecular docking study, and evaluation of the antiproliferative action of a new group of propargylthio- and propargylselenoquinolines”, Med. Chem. Res., 23, 3468-3477 (2014).

32. A. Orchel, A. Kulczycka, E. Chodurek, E. Bębenek, P. Borkowska, S. Boryczka, J. Kowalski, Z. Dzierżewicz, “Influence of betulin and 28-O-propynoylobetulin on proliferation and apoptosis of human melanoma cells (G-361)”, Post Hig Med Dośw., 68, 191-197, 2014.

33. B. Morak-Młodawska, K. Pluta, M. Zimecki, M. Jeleń, J. Artym, M. Kocięba, „Synthesis and selected immunological properties of 10-substituted 1,8-diazaphenothiazines”, Med. Chem. Res. 24, 1408-1418 (2015).

34. M. Jeleń, E. I. Bavavea, M. Pappa, A. P. Kourounakis, B. Morak-Młodawska, K. Pluta, “Synthesis of Quinoline/Naphthalene-containing Azaphenothiazines and their Potent in Vitro Antioxidant Properties”, Med. Chem. Res. 24, 1725-1732 (2015).

35. K. Marciniec, A. Maślankiewicz, M. J. Maślankiewicz, “Synthesis of some 6- and 8-halogeno-substituted 3-quinoline-sulfonic acid derivatives “, J. Heterocycl. Chem., 52, 1019-1025 (2015).

36. P. Zajdel, V. Canale, A. Partyka, K. Marciniec, G. Satała, R. Kurczab, A. Siwek, M. Jastrzębska-Więsek, A. Wesołowska, T. Kos, P. Popik, A. J. Bojarski, „Arylsulfonamide derivatives of (aryloxy)ethylpiperidines as 5-HT7 antagonists and their psychotropic properties”. Med. Chem. Commun., 6, 1272-1277 (2015).

37. R. D. Wojtyczka, A. Zięba, A. Dziedzic, M. Kępa, D. Idzik, „An activity of thioacyl derivatives of 4-aminoquinolinium salts towards biofilm-producing and planktonic forms of coagulase-negative staphylococci”, BioMed. Research Int., 1-10 (2015).

38. M. Jeleń, K. Pluta, M. Zimecki, B. Morak-Młodawska, J. Artym, M. Kocięba „6-Substitu-ted 9-fluoroquino[3,2-b]benzo[1,4]thiazines display strong antiproliferative and antitumor properties”, Eur. J. Med. Chem., 89, 411-420 (2015).

39. K. Lodarski, J. Jończyk, N. Guzior, M. Bajda, J. Gładysz, J. Walczyk, M. Jeleń, B. Morak-Młodawska, K. Pluta, B. Malawska „Discovery of butyrylcholinesterase inhibitors among derivatives of azaphenothiazines”, J. Enzyme Inhib. Med. Chem., 30, 98-106 (2015).

40. M. Jeleń, E. I. Bavavea, M. Pappa, A. P. Kourounakis, B. Morak-Młodawska, K. Pluta “Synthesis of Quinoline/Naphthalene-containing Azaphenothiazines and their Potent in Vitro Antioxidant Properties”, Med. Chem. Res., 24, 1725-1732 (2015).

41. B. Morak-Młodawska, K. Pluta, M. Zimecki, M. Jeleń, J. Artym, M. Kocięba „Synthesis and selected immunological properties of 10-substituted 1,8-diazaphenothiazines”, Med. Chem. Res., 24, 1408-1418 (2015).

42. K. Laba, P. Data, P. Zassowski, P. Pander, M. Lapkowski, K. Pluta, A. P. Monoman „Diquinoline Derivatives as Materials for Potential Optoelectronic Applications” J. Phys. Chem. C, 119, 13129-13137 (2015).

43. M. Jeleń, K. Pluta, K. Suwińska, B. Morak-Młodawska, M. Latocha, A. Shkurenko "Quinonaphthothiazines, syntheses, structures and anticancer activities", J. Mol. Struct., 1099, 10-16 (2015).

44. E. Bębenek, E. Chodurek, A. Orchel, Z. Dzierżewicz, S. Boryczka, „Antiproliferative activity of novel acetylenic derivatives of betulin against G-361 human melanoma cells”,  Acta Poloniae Pharmaceutica - Drug Research, 72, 699-703 (2015).

45. A. Kowalska, M. Latocha, K. Pluta „Synthesis and anticancer activity of thiosubstituted purines, Med. Chem. Res., 24, 3107-3116 (2015).

46. M. Latocha, A. Zięba, R. Polaniak, D. Kuśmierz, A. Nowosad, M Jurzak, E. Romuk, M. Kokocińska, E. Sliupkas-Dyrda, „Molecular effects of amine derivatives of phenothiazine on cancer cells C-32 and SNB-19 in vitro”, Acta Poloniae Pharmaceutica - Drug Research, 72, 909-915 (2015).