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Search for "bile acids" in Full Text gives 12 result(s) in Beilstein Journal of Organic Chemistry.
Revisiting the bromination of 3β-hydroxycholest-5-ene with CBr4/PPh3 and the subsequent azidolysis of the resulting bromide, disparity in stereochemical behavior
Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9
- acts as fluidity buffer, permeability switch, and consequently in cell signaling pathways. Physiologically, cholesterol is the substrate for the biosynthesis of steroidal hormones, vitamin D and bile acids [1][2]. Although cholesterol can adopt 256 stereoisomeric structures, biological significances
Synthesis of new bile acid-fused tetrazoles using the Schmidt reaction
Beilstein J. Org. Chem. 2021, 17, 2611–2620, doi:10.3762/bjoc.17.174
- selective activity towards certain tumor cell lines. Keywords: antiproliferative activity; Schmidt reaction; steroids; tetrazoles; trimethylsilyl azide; Introduction Bile acids are naturally occurring steroidal surfactants that play various biological roles. Besides the well-known role as lipid
- solubilizers, bile acids are now recognized as metabolism regulators through specific receptors: farnesoid X receptor (FXR) and Takeda G protein receptor 5 (TGR5) [1][2][3]. Research efforts to find ligands for these receptors initiated several synthetic studies where bile acids are being used as a starting
- material [4][5][6][7]. Aggregation and interactions with the cell membrane of bile acid molecules can alter drug action [8][9]. Our previous work showed that bile acids could interact with certain drug molecules and improve their biological activity [10][11]. To evade the membranolytic action of natural
Steroid diversification by multicomponent reactions
Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121
- synthetic program towards steroid-based supramolecular receptors [28]. There, steroidal diamines and diisocyanides derived from bile acids were employed in a procedure known as MiBs, i.e., multiple multicomponent macrocyclization including bifunctional building blocks. In a series of subsequent reports
Low-budget 3D-printed equipment for continuous flow reactions
Beilstein J. Org. Chem. 2019, 15, 558–566, doi:10.3762/bjoc.15.50
- results for the synthesis of methyl glycoside 3 were obtained using an overall flow rate of 200 μL/min leading to a residence time of 5 min and a yield of 44%. A similar Koenigs–Knorr type glycosylation under continuous flow has only been described previously for glucuronidation of bile acids [36
Crystal structure of the inclusion complex of cholesterol in β-cyclodextrin and molecular dynamics studies
Beilstein J. Org. Chem. 2018, 14, 838–848, doi:10.3762/bjoc.14.69
- significant role in biology as an essential structural component of the cell walls and as precursor for the biosynthesis of several substances such as vitamin D, bile acids and steroid hormones. However, the consumption of food rich in cholesterol like meat, eggs and dairy products has been associated with
Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review
Beilstein J. Org. Chem. 2018, 14, 470–483, doi:10.3762/bjoc.14.33
- times and lower costs for the chemical and enzymatic reactions involved. Keywords: bile acids; biotransformation; hydroxysteroid dehydrogenases; production process; UDCA; Introduction Ursodeoxycholic acid (UDCA), is applied in the pharmaceutical industry (Figure 1) [1]. As reported in several papers
- ) in the treatment against biliary calculus, since it possesses high efficacy and total absence of side effects [11]. UDCA is commonly produced by transformation of cholic acid (CA), which is the most abundant and least expensive bile acid available. Because of the molecular complexity of bile acids
- for this multistep synthesis will be discussed. Review Precursor availability Bile acids The most important active ingredients of bile are the bile acids. Together with their salts, they allow the emulsification of lipids, a fundamental step for their absorption and digestion. Bile acids are 24-carbon
Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands
Beilstein J. Org. Chem. 2017, 13, 564–570, doi:10.3762/bjoc.13.55
- )anthraquinones with a series of cations demonstrated their high binding affinity to Cu2+, Al3+, and Cr3+. Keywords: amination; aminocholanes; bile acids; cation complexation; Cu-catalysis; diaminoanthraquinone; Pd-catalysis; Introduction Bile acids are known to ensure vital processes in vertebrate organisms
- , including metabolism and fat digesting [1][2]. The biological activity of bile acids is mainly based on the properties of their backbone. All bile acids possess a rigid cholane skeleton with two distinct surfaces. The inward hydrophilic surface (with several hydroxy groups) along with the outward
- hydrophobic face permit bile acids to act as facial amphiphiles [3]. Their carboxylic and hydroxy groups can be easily modified, and the chemistry of these processes has been thoroughly studied [4]. All these options make bile acids the molecules of choice for many applications. The choice of bile acids as
Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners
Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208
- ) is an amphiphilic-like steroidal constituent of eukaryotic cell membranes. It acts as fluidity buffer and it is essential for membrane integrity and permeability. Besides, it is a substrate for the biosynthesis of steroidal hormones, bile acids and vitamin D. Pathological accumulation of oxygenated
Electrochemical oxidation of cholesterol
Beilstein J. Org. Chem. 2015, 11, 392–402, doi:10.3762/bjoc.11.45
- fluidity. It also serves as a precursor for the biosynthesis of steroid hormones, bile acids, and vitamin D [1]. The chemical oxidation of cholesterol is a crucial reaction in the synthesis of many compounds that are of pharmaceutical importance [2][3]. At the close of the previous century, special
A study on the inhibitory mechanism for cholesterol absorption by α-cyclodextrin administration
Beilstein J. Org. Chem. 2014, 10, 2827–2835, doi:10.3762/bjoc.10.300
- ]. Formation of micelles comprising cholesterol, lecithin and bile salts is a very important process in enhancing cholesterol absorption from the lumen of the small intestine [22][23]. The ring size in α-CD is smaller than bile acids, so it has been reported that α-CD has a low affinity for bile acids [5][24
Self-assembly of 2,3-dihydroxycholestane steroids into supramolecular organogels as a soft template for the in-situ generation of silicate nanomaterials
Beilstein J. Org. Chem. 2013, 9, 1826–1836, doi:10.3762/bjoc.9.213
- separately the hydrogen-bond donor (HBD, α), hydrogen-bond acceptor (HBA, β), and polarizability (π*) properties as contributions to the overall solvent polarity had also been occasionally used to study solvent–gelator specific interactions [20][21]. LMOGs based on cholesterol and bile acids offered the most
Advances in synthetic approach to and antifungal activity of triazoles
Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79
- -lactams and terminal alkynes of bile acids in the presence of a Cu(I) catalyst (click chemistry) by Vatmurge et al. The synthesized compounds were evaluated for their antifungal activity against different fungal strains such as Candida albicans, Cryptococcus neoformans, Benjaminiella poitrasii, Yarrowia
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