Holovatiuk V. Synthesis of new derivatives of five membered nitrogen-containing heterocyclic compounds via metathesis reactions

Українська версія

Thesis for the degree of Candidate of Sciences (CSc)

State registration number

0417U000471

Applicant for

Specialization

  • 02.00.13 - Нафтохімія і вуглехімія

03-03-2017

Specialized Academic Board

Д 26.220.01

V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine

Essay

New derivatives of five membered nitrogen-containing heterocyclic compounds, which were synthesized via metathesis reactions. Metathesis ruthenium carbene catalysts obtaining, development of synthesis of new five membered nitrogen-containing heterocyclic derivatives by ring-closing metathesis and cross-metathesis, examination of biological activity. Chemical synthesis, column chromatography, vapor phase chromatography, TLC, NMR spectroscopy, elemental analysis, QSAR-method. Methods of bisphosphine ruthenium carbene benzylidene and phenylindenylidene complexes obtaining were optimized, new monophosphine and phosphineless catalysts were synthesized. New pyrroline containing sulfonylamide five-membered cyclic sulfone derivatives and new spirocycloalkenic pyrazolidine-3,5-dione derivatives were taken in the ring-closing metathesis. It was obtained new functionalized unsaturated N-substituted 3,5-dimethylpyrazole derivatives by cross-metathesis. It was revealed by the QSAR-analysis method and via experimental research, that synthesized compounds have a low toxicity and show analgesic, anti-inflammatory and antituberculosis activities, and cytotoxic action against human cancer cell lines (MGC-803, MCF-7, SMMC-7721), as well as might inhibit HIV-1 reverse transcriptase and protein tyrosine phosphatase 1B (PTP 1B). The results can be useful in the field of petrochemistry and bioorganic chemistry.

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