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Xanthone-boronic acids: An insight into the synthesis of borylated xanthone derivates
Houngbedji, Priam-Amedeo ; Doležal, Martin (advisor) ; Zitko, Jan (referee)
CHARLES UNIVERSITY FACULTY OF PHARMACY IN HRADEC KRÁLOVÉ DEPARTMENT OF PHARMACEUTICAL CHEMISTRY AND PHARMACEUTICAL ANALYSIS DIPLOMA THESIS XANTHONE-BORONIC ACIDS: AN INSIGHT INTO THE SYNTHESIS OF BORYLATED XANTHONE DERIVATIVES Supervisor: prof. PharmDr. Martin Doležal, Ph.D. HRADEC KRÁLOVÉ 2021 PRIAM-AMEDEO HOUNGBEDJI Abstract - English The development of Bortezomib 5 and discovery of its potential in the treatment of multiple myeloma has sparked hope, and a close attention is paid in medicinal chemistry to the synthesis of boronic acid derivatives as well as the evaluation of their anticancer, antimicrobial, and other activities. Parallelly, xanthones and xanthone derivatives are compounds thoroughly studied for their potential in the treatment of cancer, and their good antimicrobial, anti-inflammatory, antiviral and anticonvulsant activity. It is only natural that efforts are oriented towards the synthesis of xanthone boronic derivatives. 3,6-Dihydroxyxanthone 10 was chosen as a precursor for the development of a procedure to borylate xanthones, mainly due to its easy synthesis and availability. From 10, 3,6-ditrifylxanthone 11 was easily prepared. The synthesis of 3,6- bis(pinacolatoboron)xanthone 8 from 11 was achieved using bis(pinacolatodiboron) B2pin2 as a borylation agent under Pd(dppf)Cl2 catalysis...
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Xanthone-boronic acids: An insight into the synthesis of borylated xanthone derivates
Houngbedji, Priam-Amedeo ; Doležal, Martin (advisor) ; Zitko, Jan (referee)
CHARLES UNIVERSITY FACULTY OF PHARMACY IN HRADEC KRÁLOVÉ DEPARTMENT OF PHARMACEUTICAL CHEMISTRY AND PHARMACEUTICAL ANALYSIS DIPLOMA THESIS XANTHONE-BORONIC ACIDS: AN INSIGHT INTO THE SYNTHESIS OF BORYLATED XANTHONE DERIVATIVES Supervisor: prof. PharmDr. Martin Doležal, Ph.D. HRADEC KRÁLOVÉ 2021 PRIAM-AMEDEO HOUNGBEDJI Abstract - English The development of Bortezomib 5 and discovery of its potential in the treatment of multiple myeloma has sparked hope, and a close attention is paid in medicinal chemistry to the synthesis of boronic acid derivatives as well as the evaluation of their anticancer, antimicrobial, and other activities. Parallelly, xanthones and xanthone derivatives are compounds thoroughly studied for their potential in the treatment of cancer, and their good antimicrobial, anti-inflammatory, antiviral and anticonvulsant activity. It is only natural that efforts are oriented towards the synthesis of xanthone boronic derivatives. 3,6-Dihydroxyxanthone 10 was chosen as a precursor for the development of a procedure to borylate xanthones, mainly due to its easy synthesis and availability. From 10, 3,6-ditrifylxanthone 11 was easily prepared. The synthesis of 3,6- bis(pinacolatoboron)xanthone 8 from 11 was achieved using bis(pinacolatodiboron) B2pin2 as a borylation agent under Pd(dppf)Cl2 catalysis...
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The effect of pyrazine derivatives on secondary metabolites content in plant cultures in vitro II.
Hanzlíková, Tereza ; Tůmová, Lenka (advisor) ; Karlíčková, Jana (referee)
The main purpose of the theses was to find if the abiotic elicitor 2,4,6-trimethyl-N-(pyrazine- 2-yl)benzenesulfonamide has any influence on the secondary metabolites production in callus and suspension cultures of Hypericum perforatum L. The cultivation was taking place in the Murashige a Skoog (MS) nutrient medium enriched by the growth regulator - alpha-naphthyl acetic acid at the concentration of 1 mg.L-1 . The elicitor was added to the cultures at the three levels of concentration: c1= 100.0 mg/100 ml; c2= 10.0 mg/100 ml; c3= 1.00 mg/100 ml. The individual samples were taken after 6, 24, 48, 72 and 168 hours of the elicitor application. The control samples without the elicitor were taken after 6, 48 and 168 hours. The collected samples were dried and subsequently transformed into methanol extracts in order to determine secondary metabolites content (rutin, hyperoside and quercetin) by HPLC method. Release of these metabolites into nutrient media was also subject of this observation. The elicitation has influenced production of the secondary metabolites, particularly in callus cultures, wherein several statistically significant values, characterizing increase in their production, were measured. The highest content of rutin (0.169 mg.g-1 DW) was determined in callus culture after 168 hours when...
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The effect of pyrazine derivatives on secondary metabolites content in plant cultures in vitro I.
Graclíková, Bohumila ; Tůmová, Lenka (advisor) ; Siatka, Tomáš (referee)
1 Abstract Elicitation method is one way to increase the production of secondary metabolites in in vitro of plant cultures and this work deals with this problem. Its aim was to find the positive effect of 2-hydroxy-4-(imidazo[1,2-a]pyrazine-2-carboxamide)benzoic acid from the group of pyrazine derivates on the production of isoflavonoids in in vitro cultures of Genista tinctoria L. Isoflavonoids play an important role in therapy of climacteric problems or they are promising substances of therapy various cancer types due to their affinity to estrogens β-receptors. This plant or rather its in vitro cultures are a potencial sources of isoflavonoids. Suspension and callus cultures of Genista tinctoria L. were used for elicitation. They were cultivated on Schenk & Hildebrant medium with the addition of 2,4-dichlorophenoxyacetic acid (2,4-D) as growth regulator at a concentration of 1 ml/l. The elicitor solution was added to the cultures at three concentrations: 3.3642 × 10-3 mol/l; 3.3642 × 10-4 mol/l; 3.3642 × 10-5 mol/l. The samples were taken at intervals of 6, 24, 48, 72 and 168 hours and then they were analyzed by HPLC method. At the same time intervals the samples of medium, where isoflavonoids were released, were analyzed. The biggest production of isoflavonoid was reached in suspension culture. The...
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