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Search for "toxicity" in Full Text gives 359 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles
Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86
- been also an advanced intermediate in the synthesis of alkaloids. For instance, hydrogenation of 117 yielded (+)-coniine (118), the major alkaloid extracted from poison hemlock and responsible for its toxicity, as its hydrochloride, and N-Boc protected derivative of 117 submitted to Wacker oxidation
Synthetic accesses to biguanide compounds
Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82
Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications
Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76
- compared to second generation 2'-O-MOE antisense oligonucleotides [162][163]. The cEt also demonstrate an improved toxicity profile in comparison to standard LNA ASOs [162]. The arduous synthesis of the nucleoside analogues has been refined to minimize the number of needed stereochemical adjustments and
Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides
Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75
- ]. Clinical trial safety assessments of this formulation showed no liver toxicity and no immune stimulation, with ≈10% of trial participants experiencing mild to moderate adverse events upon administration [38]. It includes encapsulation of siRNA by a mixture of lipid components, such as an ionizable cationic
- aptamers and peptides within the LNPs or to optimize the ratio of LNPs to cells in order to reduce toxicity in any cell line tested. Discussion LNPs represent an increasingly popular modality for cargo delivery. The vast improvements in lipid design and architecture have resulted in several successful LNP
- -driven vaccines and therapeutics, including two RNA-based severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) vaccines [46], as well as an siRNA–LNP for the treatment of a transthyretin amyloidosis [36]. However, further improvements in toxicity profiles, cargo delivery, and cell or organ
[2 + 1] Cycloaddition reactions of fullerene C60 based on diazo compounds
Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55
- to dementia have been demonstrated [39][40]. Moreover, it is noted that the almost nonexistent toxicity of the C60 derivatives allows to use them in living systems without negative consequences. Studies on the use of C60 derivatives in micro- and nanoelectronics are also important and very promising
- first gave ester 181 and then acid 182 (Scheme 31), the sodium and potassium salts of which are well soluble in water. The compound has antiviral and anticancer activity as well as pronounced antioxidant properties combined with low toxicity. Diarylmethanofullerene 183 was synthesized according to
Valorisation of plastic waste via metal-catalysed depolymerisation
Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53
- kinetics, cost of metals, toxicity, difficulty in catalyst reusing and need of downstream processing. Significant efforts have thus been made to develop greener and sustainable catalytic systems featuring high efficiency under mild conditions. The use of sodium carbonate or bicarbonate as ecofriendly
- catalysts in the form of ionic liquids (ILs) [209]. Advantages of metallated ILs include low flammability, high thermal stability and versatility. However, their “greenness” and toxicity are still debated [225][226]. Thus, amim[ZnCl3] (amin = 1-allyl-3-methylimidazolium, Table 4, entry 1) [227] and amim
Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols
Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52
- to its toxicity, the oxidation rate affording trans-diols was very slow in comparison to that for cis-diols. Using an even longer reaction time and stoichiometric amount of the reagent, diol 5 was not oxidized to the corresponding dicarbonyl compound 8. However, using NaOCl·5H2O as an oxidant [31
A new and efficient methodology for olefin epoxidation catalyzed by supported cobalt nanoparticles
Beilstein J. Org. Chem. 2021, 17, 519–526, doi:10.3762/bjoc.17.46
- , Mn and mainly Co-based catalysts for olefin epoxidation. Besides their low cost and low toxicity, the choice of these metals is related to their known ability to activate dioxygen in natural processes catalyzed by metal-containing enzymes [29][30]. Despite that various homogeneous [31][32] and
The synthesis of chiral β-naphthyl-β-sulfanyl ketones via enantioselective sulfa-Michael reaction in the presence of a bifunctional cinchona/sulfonamide organocatalyst
Beilstein J. Org. Chem. 2021, 17, 494–503, doi:10.3762/bjoc.17.43
- , respectively) gave the two highest results, but the use of dioxane is best avoided due to its toxicity. Except for hexane (only 6% ee, Table 1, entry 13), which resulted in an almost racemic product presumably due to solubility issues, all other solvents afforded the target SMA adduct with similar moderate ee
The preparation and properties of 1,1-difluorocyclopropane derivatives
Beilstein J. Org. Chem. 2021, 17, 245–272, doi:10.3762/bjoc.17.25
Total synthesis of decarboxyaltenusin
Beilstein J. Org. Chem. 2021, 17, 224–228, doi:10.3762/bjoc.17.22
- agreement with the NMR data measured by us, what leaves no reasonable doubt that the synthesized structure 1 is identical with the natural product. Decarboxyaltenusin (1) was screened for toxicity towards human HeLa cells but proved nontoxic at biologically relevant concentrations and showed an LD50 value
A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach
Beilstein J. Org. Chem. 2021, 17, 203–209, doi:10.3762/bjoc.17.20
- times if compared with toluene. We therefore selected CPME as the most suitable solvent for our purposes. Interestingly, besides being characterized by low toxicity, CPME has a very low affinity to water, making it suitable for moisture sensitive reactions, without previous distillation [31][32][33
Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine
Beilstein J. Org. Chem. 2021, 17, 28–41, doi:10.3762/bjoc.17.4
- as an early warning signal to the attacker. The fluid toxicity and bitterness, added to the characteristic odor of these insects, have been regarded as a protection against insect or vertebrate predators [3]. Bicyclic ring systems bearing a nitrogen bridge are often found in nature [4][5][6]. Typical
- concentration of coccineline found in C. septempunctata [31]. This difference may occur to compensate (−)-adaline's lower toxicity than coccineline. Biosynthetic studies carried out by Laurent et al. [33][34] showed that adults of A. bipunctata incubated in vitro with [14,14,14-3H3]myristic acid incorporated
Chemical constituents of Chaenomeles sinensis twigs and their biological activity
Beilstein J. Org. Chem. 2020, 16, 3078–3085, doi:10.3762/bjoc.16.257
- (betulinic acid) and 8 (apigenin) also exhibited significant activity with IC50 values of 4.3 and 16.6 μM, respectively. Tolstikov et al. reported that betulin (9) and its derivatives showed antiviral and antitumor effects [41]. Interestingly, betulinal (11) has an advantage in view of toxicity as compared
- compounds, only compound 8 (apigenin) exhibited a weak activity on the NGF release with a stimulation level of 127.8 ± 2.0% without displaying cell toxicity (100.9 ± 0.6%). Conclusion A new megastigmane-type norsesquiterpenoid glycoside 1 was isolated along with 11 known compounds from the MeOH extract of C
Metal-free nucleophilic trifluoromethylselenolation via an iodide-mediated umpolung reactivity of trifluoromethylselenotoluenesulfonate
Beilstein J. Org. Chem. 2020, 16, 3032–3037, doi:10.3762/bjoc.16.252
- particular by combining heteroatoms, such as chalcogens, and fluorinated moieties [16]. Despite, the negative reputation of selenium due to its toxicity at high doses, it is an essential trace element for human physiology and biochemistry [17][18][19][20]. Furthermore, selenolated compounds found valuable
Ultrasound-assisted Strecker synthesis of novel 2-(hetero)aryl-2-(arylamino)acetonitrile derivatives
Beilstein J. Org. Chem. 2020, 16, 2929–2936, doi:10.3762/bjoc.16.242
- toxicity effects are predictable for the new compounds 2c, 2i, and 2l at concentrations ranging at their solubility maxima. The possible antimutagenic effect of the selected C-substituted α-aminoacetonitriles 2c, 2i, and 2l, respectively, in the presence of 2-aminoantracene, daunomycin (mutagens for TA 98
A proposed sustainability index for synthesis plans based on input provenance and output fate: application to academic and industrial synthesis plans for vanillin as a case study
Beilstein J. Org. Chem. 2020, 16, 2346–2362, doi:10.3762/bjoc.16.196
- solvent i is given by Equation 15. where the metric parameters (M) cover occupational exposure limit (OEL, ppm), LD50 (ingestion toxicity, mg/kg), LC50 (inhalation toxicity, g m−3 for 4 h), global warming potential (GWP, unitless), smog formation potential (SFP, unitless), ozone depletion potential (ODP
- , unitless), acidity-basicity potential (ABP, unitless), bioconcentration potential (BCP, unitless), persistence potential (PER, unitless), soil sorption coefficient (soil, Koc), half-life of solvent in environment (half-life, h), aquatic toxicity to fish (aqua, mg/L for 96 h), Q-phrase potential (Q-phrase
Host–guest interaction of cucurbit[8]uril with oroxin A and its effect on the properties of oroxin A
Beilstein J. Org. Chem. 2020, 16, 2332–2337, doi:10.3762/bjoc.16.194
- involve three main intermolecular forces: a hydrophobic effect, hydrogen bonding and ion–dipole interactions at the carbonyl portals [7][8][9]. The high thermal stability [10], ease of synthesis [11], general absence of cytotoxicity or toxicity [12][13] and their good molecular recognition and binding
- [21], can help to reduce the side effects and toxicity of the drug [22]. Oroxin A (OA, baicalein-7-O-glucoside, Figure 1A) is one of the active ingredients isolated from the traditional herbal medicine Oroxylum indicum (L.) Kurz of Asian countries [23][24]. Accumulating studies have shown the
Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol
Beilstein J. Org. Chem. 2020, 16, 2322–2331, doi:10.3762/bjoc.16.193
- )-ones. A selective synthetic approach to 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones was developed via the solvent-switchable reaction of furan-2,3-diones with o-aminothiophenol. Preliminary biological assays (antimicrobial, acute toxicity) of the new compounds were carried out. Keywords: acylpyruvic acid
- , inducing its attack on the carbonyl group bearing a higher partially positive charge (for partial charges comparison, see Supporting Information File 1). As we were most interested in the biological activity of BTAs 3, preliminary antimicrobial and toxicity assays of these compounds were carried out
- albicans, Cryptococcus neoformans var. grubii, Mycobacterium tuberculosis) in vitro. Acute toxicity of BTA 3a in mice was determined to be higher than 1000 mg/kg, which means that BTA 3a can be considered as low toxic. Conclusion In conclusion, we developed two interchangeable approaches to enaminones
Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones
Beilstein J. Org. Chem. 2020, 16, 2304–2313, doi:10.3762/bjoc.16.191
- arylation of the nucleophilic nitrogen atom, known as the Ullmann [6][7] reaction, and its modification by Chan and Lam [8] are favored due to the several advantages they offer versus the Pd counterpart (i.e., the Buchwald–Hartwig reaction) such as the lower cost and lower toxicity of the metal as well as
The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY
Beilstein J. Org. Chem. 2020, 16, 2272–2281, doi:10.3762/bjoc.16.188
- properties of BODIPY and the biocompatibility of dextran. The BODIPY dextran nanoparticles were characterized regarding their size, morphology, polarity, and toxicity in vitro. We demonstrate the feasibility of mechanochemistry for boronic ester formation [23] to a glycan polymer as a route of conjugation
- also performed an MTT assay of the conjugate Dex-1b to evaluate its toxicity and we could observe basically no effect on cell proliferation in the A549 cell line (see Figure S6 in Supporting Information File 1), which remained above of 60% after 24 hours of incubation over the whole concentration range
Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis
Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183
- speculated to raise toxicity issues [15]. Despite their similar size to hydrogen atoms, fluorine atoms possess a very different chemical reactivity and exert very different influences on neighboring atoms. C–H/C–F substitution in organic molecules influences practically all physical, pharmacokinetic
- liability for phospholipidosis [20], iii) an increased membrane permeability [21] and iv) the mitigation of undesired binding to the human ether a-go-go-related gene (hERG) K+ channel associated with cardiovascular toxicity [22]. Moreover, the radiochemical properties of the 18F nucleus render them crucial
Automated high-content imaging for cellular uptake, from the Schmuck cation to the latest cyclic oligochalcogenides
Beilstein J. Org. Chem. 2020, 16, 2007–2016, doi:10.3762/bjoc.16.167
- ; thiol-mediated uptake; Introduction The effective delivery of substrates of free choice into cells with minimal endosomal capture on the one hand and a minimal toxicity on the other remains one of the grand challenges in science [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]. This
- transfected with a plasmid expressing a fusion protein of HaloTag–GFP–Golgi localization sequence [63]. The HaloTags installed in the Golgi were then labeled with the reporter 26. Under these more challenging conditions, obvious problems arose from the toxicity of the transfecting agent, over- and
- (yellow areas only in Figure 7a). a) Automated HC imaging of the cellular uptake of 25, covering the concentration dependence for the HC CAPA with the cell body mask (blue), the HC CAPA with the mitochondrial mask (yellow), and the toxicity defined as the percentage of damage-free cells selected for the
Synthesis of monophosphorylated lipid A precursors using 2-naphthylmethyl ether as a protecting group
Beilstein J. Org. Chem. 2020, 16, 1955–1962, doi:10.3762/bjoc.16.162
- strong immunostimulator and therefore a valuable target for the development of novel immunomodulators. Various lipid A derivatives have been chemically synthesized in order to reduce toxicity while retaining the immunostimulatory activity. In this work, we describe a novel approach to the frequently
- (structure 1, Figure 1). It was found that lipid X retained some immunomodulatory activity while having drastically reduced toxicity [10][11]. Lipid X was also found to give partial protection against a 100% lethal dose of endotoxin in mice [11]. However, there were also studies with conflicting results that
Three new O-isocrotonyl-3-hydroxybutyric acid congeners produced by a sea anemone-derived marine bacterium of the genus Vibrio
Beilstein J. Org. Chem. 2020, 16, 1869–1874, doi:10.3762/bjoc.16.154
- pathogenic Vibrio species, suggesting the application of PHAs as a biocontrol agent [18]. Although the toxicity of 1–4 toward the producing strain was not tested, they weakly inhibited the growth of Tenacibaculum maritimum, a causative agent of skin ulcers in marine fish, at MIC values of 25 (1), 50 (2), 50
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