Intramolecular C-H⋯O hydrogen bonding in 1,4-dihydropyridine derivatives

The diastereotopy of the methylene protons at positions 2 and 6 in 1,4-dihydropiridine derivatives with various substituents has been investigated. NMR spectroscopy and quantum chemistry calculations show that the CH⋯O intramolecular hydrogen bond is one of the factors amplifying the chemical shift differences in the 1H-NMR spectra.publishersversionPeer reviewe

Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates

The ethoxycarbonylmethyl esters of 1,4-dihydropyridines were directly converted into carbamoylmethyl esters in the presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) in good to excellent yields under mild conditions. The use of TBD is crucial for the successful aminolysis of ethoxycarbonylmethyl ester of 1,4-dihydropyridines with secondary amines as without it the reaction does not proceed at all. The aminolysis reaction proceeded regioselectively, as the alkyl ester conjugated with the 1,4-dihydropyridine cycle was not involved in the reaction. Screening of other N-containing bases, such as triethylamine (TEA), pyridine, 4-(N,N-dimethylamino)pyridine (DMAP), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), imidazole, tetramethyl guanidine (TMG) and 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) as catalysts revealed no activity in the studied reaction

Synthesis, Studies of Properties and Structure-Activity Relationships of New Delivery Systems based on the Self-Assembling Polyfunctional Pyridinium Derivatives

Polyfunctional pyridinium derivatives on the 1,4-dihydropyridione scaffold possessing self-assembling properties. 1,4-DHP forms liposomes and efficiently acts as gene delivery agent. The influence of lipids head-group on transfection activity and properties of formed liposomes were studied

Structure-Activity Relationships for Delivery Agents on the Scaffold of Self-Assembling Cationic 1,4-Dihydropyridines

Cationic amphiphiles on the 1,4-dihydropyridine scaffold with bself-assembling properties form liposomes and can be used as transport systems

The Influence of Substituent on Physical-Chemical Properties of 1,4-Dihydropyridine as Delivery Agents

Cationic synthetic lipid-like compounds on the 1,4-dihydropyridine scaffold possessing self-assembling properties from liposomes and can be used for gene delivery. Thecationic 1,4-DHPs are more active than DOTAP and PEI. The aim of work is to clarify the relationships of biological activity of self-assembling 1,4-DHPs and their physical-chemical properties for individual compounds

Synthesis of Self-Assembling Cationic 1,4-Dihydropyridines as Delivery Aģents for Studies of Structure-Activity Relationsips

The aim of the work is targeted variation of substituents at the different positions of compounds for clarification the relationships of biological activity and physical-chemical properties of self-assembling 1,4-DHP`s

Synthesis and Studies of Novel Bispyridinium-1,4-Dihydropyridine Dibromides

Synthesis of novel bispyridinium dibromides on the 1,4-DHP core performed in reaction of 4-pyridyl-1,4-dihydropyridines with propargyl bromide. The evaluation of the reducing capacity and the antiradical activity of the synthesised bispyridinium dibromides confirmed that all tested compounds possessed these activities

Evaluation of Antiradical Activity and Reducing Capacity of Synthesized Bispyridinium Dibromides Obtained by Quaternisation of 4-Pyridyl-1,4-dihydropyridines with Propargyl Bromide

New bispyridinium dibromides based on the 1,4-dhydropyridine (1,4-DHP) cycle were synthesized in the reaction between 4-pyridyl-1,4-DHP derivatives and propargylbromide. It has been shown that variation of the substituent position on the pyridine as well as changes in the electronic nature of the 1,4-DHP cycle as a result of the substituent nature at the 3 and 5 positions do not affect the course of the reaction and in all cases the corresponding bispyridinium dibromides were formed. The antiradical activity, using 1,1-diphenyl-2-picrylhydrazine as a free radical scavenger, and the reducing capacity using phosphomolybdenum complexes have been evaluated for the newly synthesized compound. It has been shown that all tested 1,4-DHP bispyridinium dibromides possess reducing capacity and antiradical properties