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Anti-tumor agents: Design, Synthesis, and Biological study of N-Substituted-7-hydroxy-1-azacoumarin-3-carboxamide derivatives as potent cytotoxic agents

Bakare Safyah B.

Polish Journal of Chemical Technology

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2021

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Vol. 23, nr 1

53--59

EN

Synthesis of ethyl 7-hydroxy-1-azacoumarin-3-carboxylate (3) was developed using ethyl-7-hydroxy coumarin-3-carboxylate and ammonium solution as the key synthons. Condensation of ethyl 7-hydroxy-1-azacoumarin-3-carboxylate with ammonium acetate and aniline to give N-substituted-7-hydroxy-1-azacoumarin-3-carboxamides (7-Hydroxy -1-azacoumarin-3-carboxamide (4) and N-phenyl 7-Hydroxy-1-azacoumarin-3-carboxamide (5)). Bromo derivative (N-phenyl 6, 8-dibromo-7-hydroxy-1-azacoumarin-3-carboxamide (6)) was obtained from halogenation of compound N-phenyl 7-Hydroxy-1-azacoumarin-3-carboxamide (5) with bromine in glacial acetic acid. N-phenyl-2,5-diacetoxy-6, 8-disubstituted-Quinoline-3-carboxamides (N-phenyl 2,7-diacetoxy-Quinoline-3-carboxamide (7) and N-phenyl 2,7-diacetoxy-6,8-dibromo-Quinoline-3-carboxamide (8)) were prepared via the acetylation of compounds 5 and 6 with acetic anhydride. Five compounds 4–8 were evaluated in vitro against more than one human tumor cell lines. Among the selected compounds, 6 showed the best in vitro cytotoxicity against the human cancer cell line; MCF-7 (with IC50 = 10.12 μM). In addition, cell cycle analysis of compound 6 demonstrated cell cycle arrest at G2/M phase and Pre-G1 apoptosis.

2

Structure of a New Schiff Base of Gossypol with Ethyl 4-Amino-1-piperidine Carboxylate in the Solid and in the Solution

Przybylski P., Pyta K., Ratajczak-Sitarz M., Katrusiak A., Brzezinski B.

Polish Journal of Chemistry

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2009

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Vol. 83, nr 5

747-759

EN

Crystals of the Schiff base derivative of gossypol with ethyl 4-amino-1-piperidine carboxylate (GSPC) have been grown and subsequently examined by X-ray diffraction, FT-IR and NMR methods. The crystal space group is P21/n with a = 11.869(1) A, b = 13.540(1) capital A, ring c = 28.119(1) capital A, ring, beta = 91.22(1)° and Z = 4. In the crystal GSPC exists in the enamine-enamine tautomeric form. The intramolecular N(16)–H(16)źźźO(2), N(16’)–H(16’)źźźO(2’) hydrogen bonds assisted by the resonance of the pi-electrons in the aromatic system are the strongest. The FT-IR spectral features of the crystals are in agree - ment with the X-ray data indicating that both parts of the molecule are similarly intramolecular hydrogen-bonded but different intermolecular hydrogen-bonded, al - though the molecule is symmetrically substituted. The FT-IR as well as 1H and 13C NMR spectra have shown that in chloroform solution the enamine-enamine tautomeric form is preserved and the whole structure of GSPC be comes more symmetrical.

3

Synthesis of New Quaternary Ammonium Salts - Derivatives of Phenyl Glucopyranosides

Dmochowska B., Pellowska-Januszek L., Skorupa E., Nowacki A., Stock F., Stepnowski P., Wiśniewski A.

Polish Journal of Chemistry

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2006

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Vol. 80, nr 9

1513-1521

EN

A new series of quaternary ammonium tosylates - derivatives of phenyl beta-Dglucopyranoside - has been produced in reactions of phenyl 2,3,4-tri-O-acetyl- 6-O-tosyl-beta-D-glucopyranoside with triethylamine, trimethylamine, 4-(N,Ndimethylamino) pyridine, 2-methylpyridine and pyridine. The structures of the isolates were determined by spectral analysis, including extensive 2D NMR spectral analyses.

4

Creatinine and Creatininium Cation in Water Solution. Tautomerism and Quantitative Interpretation of the Solution Acidity Effect on 1H, 13C and 14 N NMR Chemical Shifts

Kotsyubynskyy D., Molchanov S., Gryff-Keller A.

Polish Journal of Chemistry

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2004

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Vol. 78 / nr 2

239-248

EN

1H, 13C and 14N NMR chemical shifts for creatinine in water solutions of various acidity have been measured. Analysis of these data enabled determination of the acidity constant of creatininium cation and the chemical shifts of the neutral and protonated forms of creatinine. Molecular energies and carbon and nitrogen magnetic shielding constants for various tautomeric structures of the investigated species have been calculated using the quantum chemistry method GIAO DFT B3LYP/6-311++G(2d,p). Compilation of the available experimental and theoretical results has provided additional information on the problem of tautomerism of this important biological molecule.

5

Synthesis, Nuclear Magnetic Resonance and Infrared Studies of Zinc(II) and Cadmium(II) Complexes of Thiosemicarbazones Derived from Fluorenone and p-Anisaldehyde

Akinchan N., Drożdżewski P. M., Akinchan R.

Polish Journal of Chemistry

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2002

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Vol. 76 / nr 10

1381-1387

EN

Fluorenone (FTSCH) and p-anisaldehyde (ATSCH) thiosemicarbazones react with zinc(II) and cadmium(II) acetates forming M:L 1:2 complexes, characterized by IR, 1H and 13C NMR spectra and elemental analyses. The coordination mode of the ligands is discussed and four-coordinate, pseudo-tetrahedral structures are suggested.