Search results

1

The Suzuki-Miyaura reaction in the chemical transformations of vindoline

100%

Ruszkowska J., Chrobak R., Żero P., Maurin J. K., Szawkało J., Czarnocki Z.

Acta Biochimica Polonica

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2007

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vol. 54

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issue 4

857-861

EN

Vindoline and its analogues are important constituents of the Madagascan periwinkle Catharanthus roseus, and some of them are valuable chemotherapy drugs used in treatment for some types of cancer, including leukaemia, lymphoma, breast and lung cancer. The search for semi-synthetic congeners of natural substances is still an important task for organic chemistry. In this communication we report the synthesis of five new vindoline derivatives, 15-(2-methoxyphenyl)vindoline 11, 15-(3-methoxyphenyl)vindoline 12, 15-(2-nitrophenyl)vindoline 13, 15-(3-cyanophenyl)vindoline 15, and 15-(4-cyanophenyl)vindoline 16 using the Suzuki-Miyaura reaction as the key step. X-Ray analysis of compound 16 is also reported.

2

The synthesis and the structure elucidation of N,O-diacetyl derivative of cyclic 3-hydroxymelatonin

100%

Siwicka A., Reiter R., Tian D., Wojtasiewicz K., Leniewski A., Maurin J., Błachut D., Czarnocki Z.

Open Chemistry

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2004

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vol. 2

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issue 3

425-433

EN

Melatonin was subjected to an oxidation to give 3-hydroxymelatonin. All spectroscopic data for this compound were collected. Ab initio calculations for both possible configurations were performed. X-ray data on N,O-diacetyl derivative of 3-hydroxymelatonin allowed the unambigous structure determination.

3

Retention behavior of selected alkaloids in Reversed Phase micellar chromatographic systems

88%

Petruczynik A., Noster G., Waksmundzka-Hajnos M.

Current Issues in Pharmacy and Medical Sciences

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2015

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vol. 28

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issue 2

126-130

EN

In this work, the effects of sodium dodecyl sulfate (SDS) concentrations on retention, separation selectivity, peak shapes and systems efficiency were investigated. Herein, the retention data for 11 alkaloids were determined on an RP18 silica column with mobile phases containing methanol as organic modifier, with acetate buffer at pH 3.5, and, subsequently, with the addition of sodium dodecyl sulfate (SDS). The results of this study indicate that the retention of alkaloids decreases with the increase of SDS concentration in the mobile phase. The increase of SDS concentration, however, leads to the significantly improvement of peak symmetry and the increase of theoretical plate number in all cases. The best system efficiency for most of the investigated alkaloids was obtained in a mobile phase containing 0.1 M SDS, while most symmetrical peaks were obtained through the addition of 0.3 M of SDS to the mobile phase.

4

Synthesis of vinca alkaloids and related compounds 991. A new heterocyclic system

88%

Csókási P., Gács-Baitz E., Szántay C.

Open Chemistry

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2003

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vol. 1

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issue 1

65-68

EN

Utilising our earlier intermediate obtained by the umpolung reactivity of quinolizidine enamines, a new heterocyclic system: (11bSR, 15aSR)-1,2,3,6,11,14,15,15a-Octahydro-5H-indolo [2′,3′:3,4]pyrido[2,1-j]-1,6-naphthyridin-13(12H)-one was synthesised and its biological effects evaluated. Although modest, significant and selective effects were detected.

5

New method for the study of Amaryllidaceae alkaloid biosynthesis using biotransformation of deuterium-labeled precursor in tissue cultures

88%

El Tahchy A., Boisbrun M., Ptak A., Dupire F., Chrétien F., Henry M., Chapleur Y., Laurain-Mattar D.

Acta Biochimica Polonica

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2010

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vol. 57

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issue 1

75-82

EN

Biotransformation of deuterated-4'-O-methylnorbelladine into alkaloids galanthamine and lycorine in tissue cultures of Leucojum aestivum was demonstrated using HPLC coupled to mass spectrometry. GC-MS screening was also carried to investigate other native and deuterated alkaloids. A total of six labeled alkaloids were identified indicating that 4'-O-methyl-d3-norbelladine is incorporated into three different groups of Amaryllidaceae alkaloids that are biosynthesized by three modes of intramolecular oxidative phenol coupling.

Refine search results

The Suzuki-Miyaura reaction in the chemical transformations of vindoline

The synthesis and the structure elucidation of N,O-diacetyl derivative of cyclic 3-hydroxymelatonin

Retention behavior of selected alkaloids in Reversed Phase micellar chromatographic systems

Synthesis of vinca alkaloids and related compounds 991. A new heterocyclic system

New method for the study of Amaryllidaceae alkaloid biosynthesis using biotransformation of deuterium-labeled precursor in tissue cultures