Thermal oxidative degradation of the functionally substituted 2,2′-dipyrrolylmethenes hydrobromides and difluoroborates

Yutanova, S. L.; Berezin, Mikhail Y.; Semeikin, А. S.; Антина, Е. В.; Гусева, Г. Б.; V’yugin, A. I.

doi:10.1134/s1070363213030237

Cited by 28 publications

(12 citation statements)

References 11 publications

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“…We also aimed to link the previously described synthesis of pyrroles with this dipyrrole Compounds 4.9 and 4.10 were synthesised in only three steps from 4.4 in high yields. The yields for the self-condensation reactions to produce 4.9 (73%) and 4.10 (94%) were in agreement with Yutanova et al 195 , Tu et al 194 and Ali et al 203 The yield obtained was higher than that of the 58%…”

Section: Synthesis Of Substituted Dipyrrolessupporting

confidence: 87%

“…However, the use of this method to synthesise substituted dipyrroles such as 4,4'-diethyl-3,3',5,5'-tetramethyldipyrromethene hydrobromide has produced yields ranging from 58% (Wood et al 193 ) to 98% (Tsu et.al. 194 ), and 85% (Yutanova et al 195 ), a fact perplexing to multiple reviewers.…”

Section: Caco-2 Cell Culturementioning

confidence: 99%

“…[193][194][195] The selfcondensation of pyrrole-2-carboxylate derivatives such as 3,4,5-trimethylpyrrole-2-carboxylate respectively (Figure 4.3). [193][194][195] While Tu et al 194 reported a 98% yield for this reaction, Yutanova et al 195 and Wood et al 193 reported yields of only 85% and 58% respectively. In addition, Omar et al 203 achieved the same condensation starting with 3-ethyl-2,4-dimethylpyrrole (4.8b) and acyl halides to obtain the desired dipyrrole, 4.10 with 93% yield.…”

Section: Synthesis Of Substituted Dipyrrolesmentioning

confidence: 99%

“…In fact, Tu et al 194 and Yutanova et al 195 used 98% formic acid and concentrated HBr or HCl for the reaction to obtained a greater than 90% yield. One goal of this work was to find a simple method that has the efficiency and reproducibility of this reaction.…”

Section: Synthesis Of Substituted Dipyrrolesmentioning

confidence: 99%

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Physical and chemical interactions between bile pigments and polyaromatic mutagens

Trieu¹

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A major cause of cancer in humans is exposure to mutagenic compounds. This raises the question of how humans can be protected from these environmental mutagens. Bile pigments (BPs) such as biliverdin, unconjugated bilirubin and protoporphyrin and their derivatives have recently been found to act as antioxidants and inhibit the mutagenic effects of several known environmental mutagens including 2-aminofluorene, benzo [α]pyrene, and 2-amino-1-methyl-6-phenylimido [4,5-b]pyridine. Despite these promising results, very little is known about the mechanisms by which this inhibition is achieved. Understanding these mechanisms would be useful for future drug development. Therefore, this PhD thesis aims to explore physical and chemical interactions between BPs and mutagens. Effects of BPs on the bioavailability and metabolism of mutagens were also examined in vitro using the colorectal adenocarcinoma (Caco-2 cell) monolayer model and the human liver S9 fraction.The physical interactions between mutagens and BPs were examined using three different methods:NMR, UV and effects of bioavailability. The results of the comparison of the NMR spectra of mutagens in the absence and presence of BPs showed very little changes in the chemical shifts of the protons and the changes that did occur were the result of acid/base interactions between the BPs and mutagens. The UV spectrum of each mutagen was measured in the presence and absence of varying concentrations of BPs, and there were no changes to the UV spectra of any of the compounds. Strong physical interactions or aggregation of compounds can also affect their absorption across cell monolayers and so the apparent permeability of mutagens across Caco-2 cell monolayers in the presence and absence of BPs were measured. The results indicated that BPs increased the permeability of the mutagens slightly and effected how much of the compounds remained in tight association with the monolayer but the effects were small. These experiments provided evidence to suggest that physical interactions and aggregations are unlikely to be a major contributing mechanism of the inhibitory effects of BPs on environmental mutagens.Chemical reactions between BPs and the DNA modifying metabolites of mutagens (epoxides) were studied using styrene epoxide as a model for the reactive metabolites. Styrene epoxide is commercially available, stable and less toxic than the reactive metabolites of the mutagens.Competitive reactions were performed in which BPs and their derivatives were placed in solution with guanine and allowed to react with styrene epoxide. These reactions showed that BPs and their dimethyl esters are more reactive to the epoxide than guanine. Bile pigments primarily react through their carboxylic acid groups with the mono-and di-styrene epoxide esters being the major products isolated form the reactions. The pyrrole rings in bilirubin also showed some evidence of iii reaction with styrene epoxide though the products were too unstable to isolate. Thus, it was clear that BPs can effecti...

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Section: Synthesis Of Substituted Dipyrrolessupporting

confidence: 87%

Section: Caco-2 Cell Culturementioning

confidence: 99%

Section: Synthesis Of Substituted Dipyrrolesmentioning

confidence: 99%

Section: Synthesis Of Substituted Dipyrrolesmentioning

confidence: 99%

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Physical and chemical interactions between bile pigments and polyaromatic mutagens

Trieu¹

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“…For example, the temperature of the destruction beginning of meso-phenylsubstituted zinc (II) aza-dipyrrinates under nitrogen amounts 383 °C, and that of decamethylsubstituted zinc (II) bis(dipyrrinate)s under argon reaches 379 °C, i.e. more than ~100 degrees higher than of halo- complexes under an inert argon atmosphere is comparable to thermostability of alkylsubstituted analogs thereof in an oxidizing atmosphere of air oxygen [20,21]. Thus, the temperatures of destruction start of zinc (II) and boron (III) complexes with hexamethylsubstituted dipyrrines are 280°C [20] and 199 °C [21], respectively.…”

Section: Thermograms Of Complexes [Zn(l 1 )2]-[zn(l 3 )2] and [Bf2l 1mentioning

confidence: 96%

Influence of structural factors on the thermal stability of zinc(II) and boron(III) complexes with iodo- and bromosubstituted 2,2′-dipyrrines

2015

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State of the Art of Bodipy‐Based Photocatalysts in Organic Synthesis

et al. 2021

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Photochemistry is a tremendous research field offering many synthetic possibilities to chemists. Breakthroughs in this area have been notably driven by the implementation of new classes of photocatalysts. Within this context, Bodipy (Boron-dipyrromethene) dyes possess attractive chemical and physical features such as their modularity, strong absorption under visible light irradiation, good thermal and photochemical stabilities, and high fluorescence quantum yields. As such, this class of compounds has found widespread applications in functionalized materials, biology, medicine, or organic chemistry. From an organic-synthetic point of view, excited states of Bodipy dyes have been harnessed in electron and energy transfer reactions. This minireview collates the relevant literature on the applications of these catalysts in synthetic photochemistry and provides some perspectives of this research area.

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Thermal oxidative degradation of the functionally substituted 2,2′-dipyrrolylmethenes hydrobromides and difluoroborates

Cited by 28 publications

References 11 publications

Physical and chemical interactions between bile pigments and polyaromatic mutagens

Physical and chemical interactions between bile pigments and polyaromatic mutagens

Influence of structural factors on the thermal stability of zinc(II) and boron(III) complexes with iodo- and bromosubstituted 2,2′-dipyrrines

State of the Art of Bodipy‐Based Photocatalysts in Organic Synthesis

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