Synthesis of 1,2,4-triazole dendrimers

Maes, Wouter; Verstappen, Bert; Dehaen, Wim

doi:10.1016/j.tet.2005.12.027

Cited by 15 publications

(9 citation statements)

References 33 publications

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“…[ 12 ] They are prepared through divergent or convergent iterative procedures to obtained different sizes or generations. [ 13 ] Polyamidoamine (PAMAM) dendrimers are founded on an ethylenediamine core, and branched units are constructed from methyl acrylate and ethylenediamine. [ 11 ] PAMAM dendrimers are biocompatible, nonimmunogenic, water-soluble[ 14 ] and possess empty internal cavities and have a much higher amino group density compared with conventional macromolecules, e.g., a third-generation PAMAM prepared from ammonia core has 1.24 × 10 –4 amine moieties per unit volume (cubic Angstrom units) in contrast to the 1.58 × 10 –6 amine moieties per unit volume of a conventional star polymer which are responsible for high solubility and reactivity.…”

Section: Introductionmentioning

confidence: 99%

Solubility of aceclofenac in polyamidoamine dendrimer solutions

Patel

Garala

Basu

et al. 2011

Int J Pharma Investig

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In the present study we investigated the effect of polyamidoamine (PAMAM) dendrimers on the aqueous solubility of aceclofenac. The aqueous solubility of aceclofenac was measured in the presence of dendrimers in distilled water. The effect of variables, such as pH condition, concentration, temperature and generation (molecule size) of dendrimer, has been investigated. Results showed that the solubility of aceclofenac in the dendrimer solutions was proportional to dendrimer concentration. The order in which the dendrimers increased the solubility at a constant pH condition was G3 > G0. The influence of dendrimer solution pH on the solubility enhancement of aceclofenac suggests that it involves an electrostatic interaction between the carboxyl group of the aceclofenac molecule and the amine groups of the dendrimer molecule. The solubility of aceclofenac was inversely proportional to the temperature of dendrimer solution.Different generation (G0 and G3) PAMAM dendrimers have the potential to significantly enhance the solubility of poor water-soluble drugs.

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Section: Introductionmentioning

confidence: 99%

Solubility of aceclofenac in polyamidoamine dendrimer solutions

Patel

Garala

Basu

et al. 2011

Int J Pharma Investig

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“…Our research group has been working on the synthesis of dendrimers through a nucleophilic aromatic substitution (NAS) approach that uses the substitution of (hetero)aryl halogenides with phenolates to build up dendrimers in a convergent way …”

Section: Introductionmentioning

confidence: 99%

“…This approach allows the incorporation of heterocyclic building blocks in the dendritic framework, something that has rarely been done. In this manner, dendrimers consisting of 1,3,4-oxadiazoles,15a 1,3,5-triazines,15b pyrimidines,15c and 1,2,4-triazoles 15d have been prepared. At present, the pyrimidine system seems to present an optimum within our strategy, combining an intermediate reactivity (allowing an easy synthesis) and a good structural stability.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Multi(metallo)porphyrin Dendrimers through Nucleophilic Aromatic Substitution on meso-Pyrimidinyl Substituted Porphyrins

et al. 2006

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A convergent synthetic strategy toward novel all-porphyrin dendrimers, which can be regarded as synthetic model systems of the natural photosynthetic light-harvesting antennae, was successfully explored. The dendron propagation, based on nucleophilic aromatic substitution reactions on a meso-dichloropyrimidinyl substituted porphyrin AB2 monomer, was carried out up to the second-generation dendron, and the used approach was proven to be compatible with the stepwise introduction of different metals in the successive generations. Three different metals (Pt, Zn, and Ni) could be introduced in the second-generation heptaporphyrin dendron. By applying analogous meso-dichloropyrimidinyl substituted porphyrin cores, novel multiporphyrin dendrimers were obtained.

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“…In a following syn‐elimination of hexadecyl ketene, a terminal triazolone is formed. Nucleophilic substitutions on the 3‐position of 1,2,4‐triazoles [ 15 ] and the formation of triazolone via ketene elimination [ 16 ] have been reported earlier. Further similar degradation reactions lead to the mononuclear and dinuclear triazolones.…”

Section: Resultsmentioning

confidence: 98%

Experimental and theoretical investigation on the thermal isomerization reaction of tristriazolotriazines

Jochem

Limbach

Glang

et al. 2022

J of Physical Organic Chem

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The isomerization of tristriazolotriazione with tangential substituents to radial isomers occurs in a cascade of three ring opening/rotation/ring closure steps of the central triazine. Donor substitution accelerates the isomerization which can be catalyzed by Brønsted acids. The velocity of the rearrangements drops with each step by a factor of 4, whereas the gain in heat of formation increases. Density functional theory (DFT) calculations led to transition states; their energies correspond to the experimental data. Threefold isomerization strongly affects the mesomorphic properties.

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Synthesis of 1,2,4-triazole dendrimers

Cited by 15 publications

References 33 publications

Solubility of aceclofenac in polyamidoamine dendrimer solutions

Solubility of aceclofenac in polyamidoamine dendrimer solutions

Synthesis of Multi(metallo)porphyrin Dendrimers through Nucleophilic Aromatic Substitution on meso-Pyrimidinyl Substituted Porphyrins

Experimental and theoretical investigation on the thermal isomerization reaction of tristriazolotriazines

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