13417-08-8Relevant articles and documents
Glucosylated pH-sensitive liposomes as potential drug delivery systems
Giansanti, Luisa,Mauceri, Alessandro,Galantini, Luciano,Altieri, Barbara,Piozzi, Antonella,Mancini, Giovanna
, p. 113 - 119 (2016)
The inclusion of pH-sensitive components in liposome formulations can allow a more controlled and efficient release in response to low pH typical of some pathological tissues and/or subcellular compartments. On the other hand decorating the surface of liposomes with sugar moieties attributes to lipid vesicles specificity toward lectins, sugar-binding proteins overexpressed in many tumor tissues. A novel multifunctional pH-sensitive glucosylated amphiphile was synthesized and characterized as pure aggregate component and in mixtures with a natural phospholipid. The comparison of the properties of the new glucosylated amphiphile with respect to those of a previously described cationic structural analogue demonstrates that the pH-sensitivity can strongly affect drug release, lipid organization, as well as the exposure of the glucose residues on liposome surface and their ability to interact with Concanavalin A, a plant lectin used as model system.
Cationic metallovesicles: Catalysis of the cleavage of p-nitrophenyl picolinate and control of copper(II) permeation
Scrimin, Paolo,Tecilla, Paolo,Tonellato, Umberto
, p. 5086 - 5092 (1992)
Ligand surfactants 1-3 have been synthesized. They feature a 2-(hydroxymethyl)pyridine as the ligand subunit and different lipophilic backbones which allow the formation, in aqueous solution, of different aggregates: vesicles in the case of 1 and 2, micel
Ru-Catalyzed Selective Catalytic Methylation and Methylenation Reaction Employing Methanol as the C1 Source
Biswas, Nandita,Srimani, Dipankar
, p. 10544 - 10554 (2021/07/31)
Methanol can be employed as a green and sustainable methylating agent to form C-C and C-N bonds via borrowing hydrogen (BH) methodology. Herein we explored the activity of the acridine-derived SNS-Ru pincer for the activation of methanol to apply it as a C1 building block in different reactions. Our catalytic system shows great success toward the β-C(sp3)-methylation reaction of 2-phenylethanols to provide good to excellent yields of the methylated products. We investigated the mechanistic details, kinetic progress, and temperature-dependent product distribution, which revealed the slow and steady generation of in situ formed aldehyde, is the key factor to get the higher yield of the β-methylated product. To establish the environmental benefit of this reaction, green chemistry metrics are calculated. Furthermore, dimerization of 2-naphthol via methylene linkage and formation of N-methylation of amine are also described in this study, which offers a wide range of substrate scope with a good to excellent yield.
OXYGENATED AMINO- OR AMMONIUM-CONTAINING SULFONIC ACID, PHOSPHONIC ACID AND CARBOXYLIC ACID DERIVATIVES AND THEIR MEDICAL USE
-
Page/Page column 42, (2012/12/13)
The present invention relates to oxygenated amino or ammonium-containing sulfonic acid, phosphonic acid and carboxylic acid derivatives, in particular the compounds of formula 1, 2, 3, 4, 5 or 6, and their medical use, including their use in the treatment
A structure-activity study of spermicidal and anti-HIV properties of hydroxylated cationic surfactants
Wong, Yue-Ling,Hubieki,Curfman, Christopher L,Doncel, Gustavo F,Dudding, Travis C,Savle, Prashant S,Gandour, Richard D
, p. 3599 - 3608 (2007/10/03)
The syntheses of 2-hydroxy-N-(2-hydroxyethyl)-N,N-dimethylhexadecan-1-aminium chloride [1(16)Cl] and iodide [1(16)I], 2-hydroxy-N,N,N-trimethylhexadecan-1-aminium chloride (6), N-(2-hydroxyethyl)-N,N-dimethylhexadecan-1-aminium chloride (8), N,N-bis(2-hydroxyethyl)-N-methylhexadecan-1-aminium chloride (11), and 2-hydroxy-N-(2-hydroxyethyl)-N,N-dimethyl-4-oxahexadecan-1-aminium chloride (14) are reported along with the critical micelle concentrations (cmcs), as measured by conductivity at 25°C, of 1(16)Cl, 1(16)I, 6, 8, 11, and N,N,N-trimethylhexadecan-1-aminium chloride (12). All compounds display spermicidal and virucidal activity. A plot of minimum effective concentration (MEC) in the Sander-Cramer spermicidal assay and cmc shows that 1(16)Cl and 6 have the best spermicidal activity and highest cmcs. Compounds 8, 11, and 1(16)Cl are the most active at 0.05 mg mL-1 against cell-free and cell-associated virus. In conclusion, 1(16)Cl shows the best combination of dual activity against sperm and HIV; it is a promising candidate for further preclinical studies as a topical, contraceptive microbicide.
A new strategy for the preparation of secondary amines via o- (tetrahydropyranyloxymethyl)-benzamides
Fichert, Thomas,Massing, Ulrich
, p. 5017 - 5018 (2007/10/03)
The new synthesis strategy for the preparation of secondary amines starts from N-alkyl-phthalimides which are reduced to the corresponding o- hydroxymethyl-N-alkyl-benzamides. After protection of the hydroxy group as tetrahydropyranyl ether the N-alkyl-benzamides are alkylated to o- (tetrahydropyranyloxymethyl)-N,N-dialkyl-benzamides. The deprotection of the hydroxy group and the release of the secondary amines can be achieved in execellent yields in one reaction step using aqueous acetic acid.
Betylates. 4. The synthesis and preparative nucleophilic substitution reactions of alkyl S-betylates
King, James Frederick,Skonieczny, Stanislaw,Poole, Gary Allan
, p. 235 - 243 (2007/10/02)
Alkyl S-betylates (S,S-dialkyl-S-3propylsulfonium salts), the first examples of S-betylates (sulfonioalkanesulfonic esters), have been synthesized by two routes, and their suitability as intermediates in the transformation of alcohols by nucleophilic substitution reactions examined.They have been found to react readily in stoichiometric phase transfer processes, including substrate-reagent ion-pair reactions, like their previously studied nitrogen analogues, with the following particular features: (a) they may be used with basic nucleophiles (unlike betylates), (b) they are more simply made from commercially available starting materials than betylates, and (c) they can be made by a route that avoids a final alkylation step.
