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Synteza pochodnych dibenzo[b,f]f]oksepiny podstawionych w pierścieniu aromatycznym

Tobiasz Piotr, Krawczyk Hanna

Wiadomości Chemiczne

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2021

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[Z] 75, 11-12

1238--1257

EN

Stilbene derivatives are characterized by many beneficial biomedical properties. They show, inter alia, chemopreventive [28], anti-inflammatory and antioxidant properties [29]. One of the most popular stilbene derivatives are combretastatins, which can inhibit the polymerization process of microtubules [30]. Another stilbene derivative is, for instance, resveratrol, which is characterized by wide anti-cancer properties [31]. Dibenzo[b,f]oxepines also show advantageous and interesting biomedical properties. These compounds are stilbene analogs in which the two aromatic rings bond with each other with a vinyl bridge and an oxygen atom. Many dibenzo[b,f]oxepines have strong antipsychotic, anti-inflammatory, anti-depressant, insecticidal, anti-epileptic and anticancer properties [5]. Stilbenes and their precursors – oxepines, can be derived from azo compounds that are potential molecular photoswitches. These photoswitches are used in the socalled photopharmacology. The scope of photopharmacology is designing, synthesis, studying and using drugs, which activity can be controlled by light. The purpose of photopharmacology is also to solve the problem of off-target activity and severe side effects by establishing an external modality for controlling the action of the drug. The use of such drugs in treatment could prevent systemic and environmental side effects through the selective activation of them at the molecular target [1]. These molecular photoswitches based on oxepine ring could be extremely useful in photopharmacological therapy. The combination of azo group changing its configuration with the dibenzo[b,f]oxepine group should lead to the creation of interesting compounds. This is a promising combination of the medical properties of this bioactive compound with the function of the molecular photoswitch. A method of the synthesis of a series of azo dibenzo[b,f]oxepine derivatives was developed and implemented. Synthesized compounds can be used in the future as potential molecular photoswitches. For this purpose, a 4-step synthesis was conducted, starting from the simplest substrates – a benzaldehyde derivative and 2,4-dinitrotoluene (schem. 1).

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Chromatographic analysis of p-nitrotoluenesulfonic acid oxidation products with air in alkaline water solutions

Sikora K.

Chemia Analityczna

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2002

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Vol. 47, No. 5

681-690

EN

A method of quantitative and qualitative determination of the products ofp-nitrotoluene-sulfonic acid oxidation in the samples taken from the reaction mixture containing salts of 4,4'-dinitrostilbene-2,2'-disulfonic acid. 2-sulfo-4-nitrobenzoicacid,p-nilrotoluenesulfonic acid and 4,4'-dinitrodibenzylodisulfonic-2,2' acid by means of high performance liquid chro-matography carried out in the reverse phase system was developed. Details of the analytical method and the technique of obtaining standards are discussed in the paper.

PL

Opracowano metodę ilościowego i jakościowego oznaczania produktów utleniania kwasu p-nitrotoluenosulfonowego w próbkach pobranych z mieszaniny reakcyjnej zawierającej sole kwasu 4,4'-dinitrostilbeno-2,2'-disulfonowego, kwasu 2-sulfo-4-nitrobenzoesowego, kwasu/9-nitrotoluenosulfbnowego oraz kwasu 4,4'-dinitrodibenzylo-2,2'-disulfonowego za pomocą wysokosprawnej chromatografii cieczowej prowadzonej w układzie faz odwróconych. W pracy przedstawiono dokładne omówienie metody analitycznej i sposobu uzyskania wzorców.

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N-(E)-2-Stilbenyloxymethylenecarbonyl substituted hydrazones of ortho, meta and para hydroxybenzaldehydes

Wyrzykiewicz E., Błaszczyk A., Turowska-Tyrk I.

Bulletin of the Polish Academy of Sciences. Chemistry

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2000

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Vol. 48, No. 3

213-229

EN

Twelve unknown N-(E)-2-stilbenyloxymethylenecarbonyl substituted hydra-zones of acetone and ortho, meta and para hydroxybenzaldehydes have been prepared. The N-substituted hydrazones occur as E geometrical isomers and cis/trans amide conformers (1) H NMR estimations). Crystal structures of N-(E)-2-stilbenyloxymethylenecarbonyl sub-stituted hydrazone of ortho hydroxy-benzaldehyde 10 and N-(E)-2/-(4/-chlorostilbenyloxy-methylenecarbonyl)-substituted hydrazone of meta hydroxybenzaldehyde 14 have been determined as E geometrical isomers and trans amide conformers with intra- (10) and intermolecular (14) hydrogen bonds.