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Search for "toxicity" in Full Text gives 361 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Phenylseleno trifluoromethoxylation of alkenes
Beilstein J. Org. Chem. 2024, 20, 2434–2441, doi:10.3762/bjoc.20.207
- ], electronic effects [17][18], and conformation [19][20][21]. Some trifluoromethoxylated molecules can be used as drugs in the treatment of various pathologies (Figure 1) [22][23][24][25][26][27][28][29]. On the other hand, despite its toxicity at higher doses, selenium is also an essential trace element in
Asymmetric organocatalytic synthesis of chiral homoallylic amines
Beilstein J. Org. Chem. 2024, 20, 2349–2377, doi:10.3762/bjoc.20.201
- -disubstituted homoallylic amines 50 and 56 (Scheme 11). However, the high sensitivity of silanes 49 to air and moisture along with an increased toxicity of organotin compounds 55 may be considered challenging factors in its application on a larger scale. In 2019, an interesting approach to the organocatalytic
- excellent yields (77–91%) and excellent enantioselectivities (90–96%) on a millimolar scale (Scheme 13). It is worth noting the use of optimised minimal excess of allyltributyltin (65), which to some extent addresses the higher toxicity of trialkylstannanes compared to their silicon counterparts. The
Natural resorcylic lactones derived from alternariol
Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187
- pathogens [50][51][52]. It should be noted that Alternaria alternata is a species complex and many producer strains reported in the literature were not correctly identified [53]. The rather low toxicity of alternariol and most of the further Alternaria toxins (especially those with resorcylic lactone
- solubility in the standard tests, performed in aqueous media) nor phytotoxic activity [73]. A general but not an acute toxicity of AOH has already been mentioned in late 1970ies, e.g., an activity against Bacillus mycoides at 60 μg/disc and a toxicity to HeLa cells with an ID50 value of 6 μg/mL [74]. It
- has been investigated thoroughly on its biological activities, especially on its toxicity [6][12]. Its phytotoxicity has already been noted in the first reports; it induced chlorosis when injected to the leaves of tobacco plants [110]. It turned out to be cytotoxic against HeLa and lymphoma L5178Y
O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization
Beilstein J. Org. Chem. 2024, 20, 2143–2151, doi:10.3762/bjoc.20.184
- online software ProTox 3.0 for computational toxicity assessment of the products as their LD50 values. The tested compounds mainly belong to the 4th class of acute oral toxicity with 300 < LD50 ≤ 2000 mg/kg. In addition, we used MolPredictX (https://www.molpredictx.ufpb.br) [46] to evaluate potential
- found that most of the synthesized compounds correspond to the parameters established by the Lipinski, Ghose, Veber, Egan, and Muegge rules. In silico screening of their biological profiles indicated that these new derivatives fall into the 4th class of acute toxicity. Additionally, they exhibit
Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis
Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182
- ), but is also widely used in transition-metal-catalyzed carbonylation reactions [1][2]. However, carbon monoxide is a flammable gas with a wide explosive range, although colorless and odorless, and requires special care in handling due to its high toxicity. In addition, when carbon monoxide is used in a
1,2-Difluoroethylene (HFO-1132): synthesis and chemistry
Beilstein J. Org. Chem. 2024, 20, 1955–1966, doi:10.3762/bjoc.20.171
- ; refrigerants; Introduction In the 1930s, halogenated chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) were synthesized and have been shown to have low toxicity, which has opened the door for the application as safe refrigerants [1][2]. The development of the commercial synthesis of CFCs and
- fluorinated materials are non-flammable and have low toxicity, CFCs were found to be destructive to the ozone layer of the stratosphere [1][2] due to high ozone-depleting potential (ODP). This has led to the phasing out of CFCs and the replacement with hydrofluorocarbons (HFCs), which show no significant
- blocks has significantly increased in the last years. Recently, the E-isomer of 1,2-difluoroethylene ((E)-HFO-1132) has attracted attention as a new refrigerant due to the low boiling point, moderate flammability, and low toxicity [40][41][42]. Also, in patent literature 1,2-difluoroethylene has been
2-Heteroarylethylamines in medicinal chemistry: a review of 2-phenethylamine satellite chemical space
Beilstein J. Org. Chem. 2024, 20, 1880–1893, doi:10.3762/bjoc.20.163
- comparable to the original [1]. The main purpose of this approach is quality improvement, such as activity, selectivity, bioavailability, metabolism, and/or toxicity, while expanding the chemical space surrounding bioactive compounds [2][3]. Benzene-to-heteroaromatic ring replacement represents a classical
- toxicity reports in hospital admissions. Nguyen et al. [36] investigated its effects in mice, demonstrating neurotoxicity via dopamine receptors, while Tuv et al. [37] studied the compound’s phamarcokinetics, pharmacodynamics, and mode of action in comparison to methamphetamine, which revealed a
The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)
Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162
- only for most of unhindered small ones), their partial instability and their potential toxicity [27], thus in situ generation represents a sustainable alternative for their conventional use and this issue has been recently reviewed by Baht and Heravi [28]. In situ generation of isocyanides has been
Syntheses and medicinal chemistry of spiro heterocyclic steroids
Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152
- synthesized compounds were evaluated for their DNA binding properties and screened for cytotoxicity against leukemia cancer cells (Jurkat), demonstrating IC50 values in the micromolar range (14.2 to 36.5 µM). Importantly, these derivatives exhibited minimal toxicity toward normal cells (PBMCs). Furthermore
Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty
Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146
- , other parabens were not detected. Parabens are used as preservatives in pharmaceutical, food, and cosmetic industries due to their low toxicity, stability, and activity against a broad spectrum of microorganisms [124]. Industrially, parabens are prepared starting from 4HBA, which in turn, is a
Divergent role of PIDA and PIFA in the AlX3 (X = Cl, Br) halogenation of 2-naphthol: a mechanistic study
Beilstein J. Org. Chem. 2024, 20, 1580–1589, doi:10.3762/bjoc.20.141
- halogenation via PhIX2. Keywords: aromatic bromination; aromatic chlorination; density functional theory (DFT); hypervalent iodine; iodine(III); Introduction Hypervalent iodine(III) reagents have gained attention as strong oxidants with a low toxicity [1][2][3][4][5][6][7][8] and due to the ability to mimic
Photoswitchable glycoligands targeting Pseudomonas aeruginosa LecA
Beilstein J. Org. Chem. 2024, 20, 1486–1496, doi:10.3762/bjoc.20.132
- /off or from low to high. This strategy can be used for specific targeting or local drug activation to reduce its toxicity [14]. There is an increasing use of the photoisomerization to control the conformation as well as the activities of various biomolecules with the development of photopharmacology
Hypervalent iodine-catalyzed amide and alkene coupling enabled by lithium salt activation
Beilstein J. Org. Chem. 2024, 20, 1405–1411, doi:10.3762/bjoc.20.122
- development of chiral hypervalent iodines by Wirth, Kita, Ishihara, Muñiz, and many others, have firmly established these reagents as useful catalysts for a wide variety of chemical transformations [6][7][8][9][10][11][12][13][14][15][16][17]. A number of features, including low toxicity, high stability, ease
Transition-metal-catalyst-free electroreductive alkene hydroarylation with aryl halides under visible-light irradiation
Beilstein J. Org. Chem. 2024, 20, 1327–1333, doi:10.3762/bjoc.20.116
- chemical reagents; however, these methods have some drawbacks, such as reagent toxicity/stability and limited substrate scope [12][13][14]. While recent advances in photochemistry have remarkably expanded the synthetic utility of (hetero)aryl radicals in organic synthesis [15][16][17][18][19][20], visible
Oxidative hydrolysis of aliphatic bromoalkenes: scope study and reactivity insights
Beilstein J. Org. Chem. 2024, 20, 1286–1291, doi:10.3762/bjoc.20.111
- metals, inspired by Nature's metalloproteins. However, using toxic and expensive metals is not always practical, making alternative oxidative methodologies more appealing. Enter hypervalent iodine reagents – a leading metal-free choice for oxidation reactions. These robust and low-toxicity reagents have
Light on the sustainable preparation of aryl-cored dibromides
Beilstein J. Org. Chem. 2024, 20, 1076–1087, doi:10.3762/bjoc.20.95
- context of covalent organic frameworks (COFs) and metal-organic frameworks (MOFs), frequently assembled through imine linkages. While C–H activation through halogens presents clear technical advantages, it also brings forth concerns about the toxicity of halo compounds to both human health and the
- ) greater electrophilicity of the halo compound due to better leaving group ability of the halide ion, (iii) reduced toxicity, presumably due to faster hydrolysis [18], and (iv) easier oxidation of the halide to molecular halogen (E0 = 1.087 V (SHE) for Br2/Br−; E0 = 1.358 V (SHE) for Cl2/Cl−) [19
Activity assays of NnlA homologs suggest the natural product N-nitroglycine is degraded by diverse bacteria
Beilstein J. Org. Chem. 2024, 20, 830–840, doi:10.3762/bjoc.20.75
- hexahydro-1,3,5-trinitro-1,3,5-triazine (commonly called RDX), octogen (HMX), and hexanitrohexaazaisowurtzitane (CL-20) are compounds found in military grade explosives and propellants. Contamination of these cyclic nitramines in soil and groundwater is concerning due to their toxicity and potential
- producers and of NNG is unknown. Additionally, NNG’s physiological function is unknown, but it is toxic to plants, mice, and Gram-negative bacteria [25][26]. While there is no direct evidence of the mechanism of this toxicity, NNG has been shown to competitively inhibit succinate dehydrogenase, a component
- noursei, an NNG-producing bacterium, did not reveal any NnlA homologs. Interestingly, four NMOs are annotated in the S. noursei genome. These enzymes could protect S. noursei from NNG toxicity during its biosynthesis. Meanwhile, we posit that NnlA protects non-NNG producing bacteria from exposure. In vivo
Synthesis of new representatives of A3B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations
Beilstein J. Org. Chem. 2024, 20, 767–776, doi:10.3762/bjoc.20.70
- [8]. Further improvement of the PDT method requires the search for new photosensitizers having higher photoactivity, tumor selectivity, and high singlet oxygen quantum yield, as well as low in vivo toxicity [7]. Therefore, some strategies have been developed to enhance the therapeutic efficiency of
- biomacromolecule [10][11]. In this context, fluorinated porphyrins have attracted considerable interest due to their biological properties such as low toxicity, metabolic stability, and cellular uptake. The introduction of a fluorine atom into the molecule is the feasibility to change drastically its biological
- meso-pentafluorophenyl-substituted porphyrins. Carboranes, due to their unique physical and chemical properties such as high chemical and biological stability [28][29], three-dimensional aromaticity [30][31], low toxicity [28], high hydrophobicity, and enriched boron content [32][33] are perspective
Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors
Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46
- relationship (SAR) studies on selective inhibitors reduce the prevalence of undesired effects, such as toxicity in mammals [4]. Despite being employed in the field for over three decades, the mode of action of preemergence herbicide cinmethylin (1, Scheme 1) has remained unknown until 2018. At that time, the
Switchable molecular tweezers: design and applications
Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45
Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles
Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36
- related environments [8]. The mechanism of action involves the binding of BIMs to the penicillin-restricting protein PBP2a which inhibits the biosynthesis of the bacterial cell wall, making the treatment feasible without any toxicity to human cells [9][10]. The applications of BIMs have also been extended
- counterparts, due to their recyclability, ease of handling, and low cost [40]. Carbon-based solid acid catalysts especially are an interesting catalyst class, because they display low corrosiveness, toxicity, and higher catalytic activity, while also being insoluble in most organic solvents. The large amount
Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines
Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3
- embryonic cells. Identification of the cause of the registered selective toxicity of the tested compounds requires further study. Conclusion Thus, we have introduced an effective base-catalyzed tandem reaction including a Cornforth-type rearrangement of 1-heteroaryl-1,2,3-triazole-4-carboximidamides and
1-Butyl-3-methylimidazolium tetrafluoroborate as suitable solvent for BF3: the case of alkyne hydration. Chemistry vs electrochemistry
Beilstein J. Org. Chem. 2023, 19, 1966–1981, doi:10.3762/bjoc.19.147
- 1881, Kucherov identified mercury(II) salts in sulfuric acid as efficient promoters of the hydration of alkynes and this catalyst system has found applications in industrial scale synthesis [10]. However, the toxicity and the environmental issues associated with the use of mercury-based compounds have
- ][52][53][54]. However, some of these procedures suffer from major drawbacks, such as the toxicity and/or high cost of the metal catalysts, the need to use concentrated Brønsted acids in high excess, long reaction times, and high temperatures. In addition, these reactions have been studied mainly in
Recent advancements in iodide/phosphine-mediated photoredox radical reactions
Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131
- radical reactions. These reactions have garnered much attention due to their cost-effectiveness, low toxicity, and widespread availability. Notably, the NaI/PPh3 combined system has been successfully employed in the photofixation of nitrogen [51]. Despite these remarkable progresses made, there remain
Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups
Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125
- ]. The study also found that those coordination compounds were selective towards abnormal cells, exhibiting lower toxicity for healthy human hepatocytes. On the other hand, an important development in cancer research is the use of physiological metal ion complexes, which afford more biocompatibility and
- ions. For this reason, we feel quite comfortable to state that these compounds are promising, and deserve deeper studies regarding their interactions with, for example, aluminum(III) and cell toxicity assessments. Experimental All solvents and reagents were purchased from commercial suppliers Sigma
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