V. Milišiūnaitė “Synthesis of novel condensed pyrazole ring containing heterocyclic systems and investigation of their properties” doctoral thesis defence

Author, Institution: Vaida Milišiūnaitė, Kaunas University of Technology

Science area, field of science: Physical Sciences, Chemistry, 03P

Scientific Supervisors:
Habil. Dr. Algirdas Šačkus (Kaunas University of Technology, Physical Sciences, Chemistry, 03P),
Dr. Wolfgang Holzer (University of Vienna, Physical Sciences, Chemistry, 03P).

Scientific Advisor:
Dr. Eglė Arbačiauskienė (Kaunas University of Technology, Physical Sciences, Chemistry, 03P).

Dissertation Defence Board of Chemistry Science Field:
Prof. Dr. Vytas Martynaitis (Kaunas University of Technology, Physical Sciences, Chemistry, 03P), chairman,
Prof. Dr. Vytautas Getautis (Kaunas University of Technology, Physical Sciences, Chemistry, 03P),
Prof. Dr. Linas Labanauskas (Centre for Physical Sciences and Technology,  Physical Sciences, Chemistry, 03P),
Prof. Dr. Vytautas Mickevičius (Kaunas University of Technology, Physical Sciences, Chemistry, 03P),
Prof. Dr. Patrick Rollin (University of Orleans, France, Physical Sciences, Chemistry, 03P).

The doctoral dissertation is available and at the library of Kaunas University of Technology (K. Donelaičio St. 20, Kaunas).

Annotation:

Pyrazoles and their derivatives represent a class of important nitrogen-containing heterocyclic compounds that are covering a broad range of synthetic as well as natural products that display innumerable chemical, biological, agrochemical, and pharmacological properties. The main aim of this work was design, synthesis, and investigation of novel polycyclic heterocyclic systems by employing ring-closure reactions of vic-bifunctionalized pyrazoles Derivatives of the 2H-furo[2,3-c]pyrazole can be easily obtained via the silver (I) or gold (I) ion mediated cyclisation of 4-alkynyl-1-phenyl-1H-pyrazol-3-ols. In addition, 3-alkynylpyrazole-4-carbaldehydes and the corresponding alkanones are suitable precursors for the preparation of 2H-pyrazolo[4,3-c]pyridine derivatives. A simple and straightforward approach to various benzopyrano[2,3-c]pyrazol-4(2H)-ones starting from easily available 4-aroylpyrazol-3-ols is developed. Moreover, the reaction of 3- and 5-alkynylpyrazole-4-carbaldehydes with (het)aryl diamines results in the formation of polycylic condensed heterocyclic systems. Furthemore, 1-methyl-3,5-diphenyl-3H-pyrazole[4’,3’:3,4]pyrido[1,2-a]benzimidazole can be functionalized by employing Sonogashira- and Suzuki-type coupling reactions of the corresponding intermediate bromide. Finally, 2H-pyrazolo[4,3-c]pyridine derivatives exhibit anticancer activity against K-562 and MCF-7 cancer cell lines in vitro through arresting the cell cycle in mitosis and induction of apoptosis; 2H– and 3H-pyrazole[4’,3’:3,4]pyrido[1,2-a]benzimidazole derivatives are novel fluorescent organic compounds characterized by a high quantum yield (F_f).