1-Hydroxyalkylphosphonium Salts-Synthesis and Properties.

An efficient and convenient method for the synthesis of 1-hydroxyalkylphosphonium salts is described. Reactions were carried out at room temperature, in a short time, and without chromatography for product isolation. The properties of the obtained phosphonium salts were examined and discussed.

A Small Sugar Molecule with Huge Potential in Targeted Cancer Therapy.

The number of cancer-related diseases is still growing. Despite the availability of a large number of anticancer drugs, the ideal drug is still being sought that would be effective, selective, and overcome the effect of multidrug resistance. Therefore, researchers are still looking for ways to improve the properties of already-used chemotherapeutics.

Extraction, Purification, Quantification, and Stability of Bioactive Spilanthol from Acmella oleracea.

is an ethnobotanically significant plant with a relatiwely high content of spilanthol. Due to its broad spectrum of activity, including anti-inflammatory, antioxidant, analgesic, antifungal, and bacteriostatic properties, it is considered a valuable bioactive natural product. In addition, spilanthol as its main bioactive component inhibits facial muscle contractions, making it an attractive ingredient in anti-wrinkle and anti-aging cosmetics.

Design, Synthesis and Preliminary Evaluation of the Cytotoxicity and Antibacterial Activity of Novel Triphenylphosphonium Derivatives of Betulin.

For several decades, natural products have been widely researched and their native scaffolds are the basis for the design and synthesis of new potential therapeutic agents. Betulin is an interesting biologically attractive natural parent molecule with a high safety profile and can easily undergo a variety of structural modifications. Herein, we describe the synthesis of new molecular hybrids of betulin via covalent linkage with an alkyltriphenylphosphonium moiety.

1-Aminoalkylphosphonium Derivatives: Smart Synthetic Equivalents of -Acyliminium-Type Cations, and Maybe Something More: A Review.

-acyliminium-type cations are examples of highly reactive intermediates that are willingly used in organic synthesis in intra- or intermolecular α-amidoalkylation reactions. They are usually generated in situ from their corresponding precursors in the presence of acidic catalysts (Brønsted or Lewis acids). In this context, 1-aminoalkyltriarylphosphonium derivatives deserve particular attention.

Chemo-Enzymatic Baeyer-Villiger Oxidation Facilitated with Lipases Immobilized in the Supported Ionic Liquid Phase.

A novel method for chemo-enzymatic Baeyer-Villiger oxidation of cyclic ketones in the presence of supported ionic liquid-like phase biocatalyst was designed. In this work, multi-walled carbon nanotubes were applied as a support for ionic liquids which were anchored to nanotubes covalently by amide or imine bonds. Next, lipases B from , or were immobilized on the prepared materials.

Glycoconjugation of Betulin Derivatives Using Copper-Catalyzed 1,3-Dipolar Azido-Alkyne Cycloaddition Reaction and a Preliminary Assay of Cytotoxicity of the Obtained Compounds.

Pentacyclic lupane-type triterpenoids, such as betulin and its synthetic derivatives, display a broad spectrum of biological activity. However, one of the major drawbacks of these compounds as potential therapeutic agents is their high hydrophobicity and low bioavailability. On the other hand, the presence of easily transformable functional groups in the parent structure makes betulin have a high synthetic potential and the ability to form different derivatives.

Triphenylphosphonium Analogues of Betulin and Betulinic Acid with Biological Activity: A Comprehensive Review.

Naturally occurring pentacyclic lupane triterpenoids such as betulin (1) or betulinic acid (2) and their synthetic derivatives display a broad spectrum of biological activities and, therefore, have been the subject of great interest. However, the use of these compounds as potential therapeutic agents is limited by their low bioavailability, high hydrophobicity, and insufficient intracellular accumulation. In this context, research on modifications of the parent structures that will improve their pharmacokinetic properties is particularly important.

Spectroscopic Methods in the Evaluation of Modified Vegetable Base Oils from .

Raw vegetable oil from was subjected to oxidative treatment to enhance its viscosity. The oxidation processes were carried out in the presence of -hydroxyphthalimide with or without supercritical CO₂ as a solvent. Four spectroscopic techniques (Raman, UV-VIS, FT-IR, NMR) were applied to assess the chemical changes taking place during the oxidation.

A new method for the synthesis of α-aminoalkylidenebisphosphonates and their asymmetric phosphonyl-phosphinyl and phosphonyl-phosphinoyl analogues.

A convenient approach has been developed to α-aminoalkylidenebisphosphonates and their asymmetric phosphonyl-phosphinyl and phosphonyl-phosphinoyl analogues by α-phosphonylation, α-phosphinylation or α-phosphinoylation of 1-(N-acylamino)alkylphosphonates, that, in turn, are easily accessible from N-acyl-α-amino acids. Effective electrophilic activation of the α-position of 1-(N-acetylamino)alkylphosphonates was achieved by electrochemical α-methoxylation of these compounds in methanol, mediated with NaCl, followed by displacement of the methoxy group with triphenylphosphonium tetrafluoroborate to give hitherto unknown 1-(N-acetylamino)-1-triphenylphosphoniumalkylphosphonate tetrafluoroborates. The latter compounds react smoothly with trialkyl phosphites, dialkyl phosphonites or alkyl phosphinites in the presence of Hünig's base and methyltriphenylphosphonium iodide in a Michaelis-Arbuzov-like reaction to give the expected alkylidenebisphosphonates, 1-phosphinylalkylphosphonates or 1-phosphinoylalkylphosphonates, respectively, in good yields.

1-(N-acylamino)alkyl sulfones from N-acyl-α-amino acids or N-alkylamides.

A variety of N-(1-methoxyalkyl)amides or carbamates react readily with sodium aryl sulfinates in the presence of triphenylphosphonium tetrafluoroborate or bromide in CHCl3 under mild conditions to give 1-(N-acylamino)alkyl sulfones in good yields. A combination of this reaction with the recently described electrochemical decarboxylative α-methoxylation of N-acyl-α-amino acids to give N-(1-methoxyalkyl)amides in the presence of 3-(1-piperidino)propyl-functionalized silica gel (SiO2-Pip) enables an effective two-pot transformation of N-acyl-α-amino acids to 1-(N-acylamino)alkyl sulfones. Alternatively, N-(1-methoxyalkyl)amides can be obtained by electrochemical α-methoxylation of either N-alkylamides, lactams, or N-alkylcarbamates.

1H NMR spectroscopic criteria for the configuration of N-acyl-alpha,beta-dehydro-alpha-amino acid esters.

The diagnostic values of the following three spectral criteria for the configuration of N-acyl-alpha,beta-dehydro-alpha-amino acid esters were examined: (i) the proton at the beta-position at the double bond of a Z-isomer is shielded if compared with the respective E-isomer (delta(beta)Z < delta(beta)E); (ii) the proton at the nitrogen atom is shielded in a Z-isomer in comparison with the corresponding E-isomer (delta(NH)Z < delta(NH)E); and (iii) changing of the solvent from CDCl3 to deuterated trifluoroacetic acid (TFA) causes shielding of the H(beta) vinylic proton of an E-isomer or deshielding of the respective proton of the Z-isomer (delta(CDCl3)E > delta(TFA)E or delta(CDCl3)Z < delta(TFA)Z). The investigations were based on a set of 22 (Z)- and (E)-N-acyl-alpha,beta-dehydro-alpha-amino acid esters of diverse structures, with aliphatic, aromatic and heteroaromatic substituents at the vinylic beta-carbon; most of the examined compounds were hitherto unknown. The application of the substituent effect additivity rule given by Pascual et al.