Synthesis of N,N′-bis-[3-alkoxy-4-(hydroxy, alkoxy, acyloxy)-phenylmethylene- and -Phenylmethyl]-1,3-phenylenediamines

Дикусар, Е. А.; Поткин, В. И.; Козлов, Н. Г.; Yuvchenko, A. P.

doi:10.1134/s1070363209020157

Cited by 8 publications

(9 citation statements)

References 5 publications

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“…Using elevated temperatures to promote the formation of bisamines 4 was unsuccessful. This result was in contrast to comparable systems [ 14 ], which required heat to form benzyl amine products exclusively. A preliminary examination using 1 H NMR spectroscopy suggested that twelve hours were needed to completely reduce the proposed intermediate imine 3 .…”

Section: Resultscontrasting

confidence: 65%

Bis(benzylamine) monomers: One-pot preparation and application in dendrimer scaffolds for removing pyrene from aqueous environments

Monaco¹,

Tomas²,

Kirrane³

et al. 2013

Beilstein J. Org. Chem.

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SummaryBisimine and bisamine AB2 monomers have been synthesized from 3,5-diaminobenzoic acid and benzaldehyde derivatives without the need for protective groups or purification. This monomer preparation is universal for various electron-donating and electron-withdrawing benzaldehyde substrates. To demonstrate the versatility of these previously unreported AB2 monomers in the formation of high molecular weight structures, novel first-generation dendrimers and hybrid second-generation dendrimers have been synthesized. Using fluorescence spectroscopy, pyrene was shown to be removed from an aqueous environment upon exposure to thin dendrimer films, with the first-generation dendrimer removing 70% of the pyrene within 30 min and the hybrid second-generation dendrimers removing 38–52%. Inclusion formation constants were calculated to be on the order of 109–1011 M−1 and are comparable to the values of previously reported macromolecules. These results illustrate that size may not influence pyrene removal as effectively as composition.

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Section: Resultscontrasting

confidence: 65%

Bis(benzylamine) monomers: One-pot preparation and application in dendrimer scaffolds for removing pyrene from aqueous environments

Monaco¹,

Tomas²,

Kirrane³

et al. 2013

Beilstein J. Org. Chem.

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“…The rst part of this synthesis was demonstrated in scheme 1 which deals with the preparation of pyrazole derivatives via three steps starting by the synthesis of 3-methyl-1-phenylpyrazol-5-one by the reaction of phenyl hydrazine with ethyl acetoacetate in the presence of glacial acetic acid and ethanol according to the procedure described by Khanal et al [53]. The Vilsmeier-Haack reaction of the previous step afforded 5-chloro-3-methyl-1-phenylpyrazole-4-carboxaldehyde 14 which followed by introduction of nucleophiles i.e secondary amines or phenol derivatives to give compounds 15-21 (Scheme 1) [53][54][55][56] Based on the predicted binding a nities and interactions, compounds 47 and 48 were selected as top-scoring compounds and modi cation of the polar head to possess the NO 2, group, was planned. Unfortunately, the low yield and poor solubility caused no synthesis of other derivatives of nitro-analogues.…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of new pyrazolylbenzimidazoles as sphingosine kinase-1 inhibitors

et al. 2021

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Sphingosine-1 Kinase (SphK-1) is one of the important enzymes of phospholipids and it is inhibition is one of the therapeutic strategies for different diseases. SphK1 over expression is observed in different types of cancer that indicating its important role in tumor growth. In search of effective SphK-1 inhibitors, a new series of pyrazolylbenzimidazoles was synthesized and evaluated as sphingosine1-kinase (Sphk-1) inhibitors. In order to evaluate the binding a nities of all the synthesized compounds, all compounds were subjected to docking analysis and uorescence quenching. The results indicated that there is a consistency between the docking and the uorescence quenching results which revealed that compounds 47 and 48 exhibited signi cant decrease in the uorescence intensity of SphK1 as well as they formed stable protein-ligand complexes. In addition, Enzyme inhibition assay was performed and showed effective inhibitory potential towards SphK-1. Moreover, IC 50 values was calculated and displayed that compounds 47 and 48 were the most promising compounds. In addition, antiproliferation study for all the synthesized compounds was performed against NCI 60-cell line panel. The target compounds 47 and 48 demonstrated effective antitumor activity inhibitory potential to the SphK-1. Most of these compounds t well into the ATP-binding site of SphK1 and form signi cant hydrogen-bonding interactions with catalytically relevant residues as predicted by molecular docking. In this article, insight has been given for the importance of pyrazolylbenzimidazoles as Sphk1 inhibitors and the perspectives that they hold for future research.

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Section: Resultsmentioning

confidence: 99%

Design and synthesis of new pyrazolylbenzimidazoles as sphingosine 1-kinase inhibitors

Galal

Omar

Khairat

et al. 2021

Preprint

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Sphingosine-1 Kinase (SphK-1) is one of the important enzymes of phospholipids and it is inhibition is one of the therapeutic strategies for different diseases. SphK1 over expression is observed in different types of cancer that indicating its important role in tumor growth. In search of effective SphK-1 inhibitors, a new series of pyrazolylbenzimidazoles was synthesized and evaluated as sphingosine1-kinase (Sphk-1) inhibitors. In order to evaluate the binding affinities of all the synthesized compounds, all compounds were subjected to docking analysis and fluorescence quenching. The results indicated that there is a consistency between the docking and the fluorescence quenching results which revealed that compounds 47 and 48 exhibited significant decrease in the fluorescence intensity of SphK1 as well as they formed stable protein–ligand complexes. In addition, Enzyme inhibition assay was performed and showed effective inhibitory potential towards SphK-1. Moreover, IC50 values was calculated and displayed that compounds 47 and 48 were the most promising compounds. In addition, antiproliferation study for all the synthesized compounds was performed against NCI 60-cell line panel. The target compounds 47 and 48 demonstrated effective antitumor activity inhibitory potential to the SphK-1. Most of these compounds fit well into the ATP-binding site of SphK1 and form significant hydrogen-bonding interactions with catalytically relevant residues as predicted by molecular docking. In this article, insight has been given for the importance of pyrazolylbenzimidazoles as Sphk1 inhibitors and the perspectives that they hold for future research.

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Synthesis of N,N′-bis-[3-alkoxy-4-(hydroxy, alkoxy, acyloxy)-phenylmethylene- and -Phenylmethyl]-1,3-phenylenediamines

Cited by 8 publications

References 5 publications

Bis(benzylamine) monomers: One-pot preparation and application in dendrimer scaffolds for removing pyrene from aqueous environments

Bis(benzylamine) monomers: One-pot preparation and application in dendrimer scaffolds for removing pyrene from aqueous environments

Design and synthesis of new pyrazolylbenzimidazoles as sphingosine kinase-1 inhibitors

Design and synthesis of new pyrazolylbenzimidazoles as sphingosine 1-kinase inhibitors

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