86312-75-6

Upstream product

• 31643-49-9 4-Nitrophthalonitrile 
• 100-51-6 benzyl alcohol 
• 103-16-2 4-Benzyloxyphenol 

Downstream Products

• 30757-50-7 4-hydroxy-1,2-benzenedicarbonitrile 

Relevant academic research and scientific papers

Preparation of monohydroxyphthalocyanines and their use in the synthesis of heteronuclear complexes

A directed synthesis of monohydroxyphthalocyanines has been developed; using the phthalocyanine-O-subphthalocyanine complex as an example, it has been shown that they can be used as building blocks in syntheses of heteronuclear complexes.

Bulky-substituted phthalodinitriles and cobalt and copper phthalocyanines based on them: synthesis, thermal analysis and spectroscopic properties

By the nucleophilic substitution of the nitro group in 4-nitrophthalononitrile for the residues of alkoxy-substituted phenols, the synthesis of alkoxyphenoxyphthalonitriles was carried out. By template condensation of the substituted phthalonitriles obtained with copper and cobalt acetates at 200?°C, the corresponding phthalocyaninates were obtained. The conditions for the isolation and purification of the complexes synthesized were selected. The stability of substituted phthalonitriles and phthalocyaninates synthesized based on them regarding to heating in an argon–oxygen medium was evaluated (1:1 ratio). It was found the compounds obtained are thermally stable, and the destruction of phthalocyanines begins at lower temperatures compared to the corresponding phthalonitriles. For the complexes synthesized, the spectroscopic properties in organic solvents and concentrated sulfuric acid were studied. The influence of the nature of the substituent, metal complexing agent and solvent on the nature of the spectroscopic curves and the position of the main absorption band of phthalocyanine complexes has been established. It is noted passing from polar aprotic solvents to nonpolar ones, a shift of the maximum of the Q absorption band for the studied macrocycles was observed. Electronic absorption spectra in sulfuric acid show a significant bathochromic shift of the absorption band. An increase in the length of the alkyl substituent practically was found not to affect the position of the absorption maximum. Passing from complexes with Co(II) to Cu(II), a bathochromic shift of the absorption maximum was observed.

Synthesis and self-assembly of phthalocyanine-tethered block copolymers

A series of novel phthalocyanine (Pc)-tethered block copolymers, Pc-poly(methyl methacrylate)-block-polystyrene (Pc-PMMA-b-PS), with various molecular weights (number average molecular weight mass = 41, 66, 86 kg mol-1), were prepared by atom transfer radical polymerization and click chemistry. The structurally related Pc-tethered homopolymer, Pc-PMMA was also synthesized for comparison. Pc-PMMA forms homogeneous polymer films containing π-assemblies of the terminal Pc groups, whereas Pc-PMMA-b-PS self-assembles into a cylindrical morphology in which the Pc units show π-π interactions inside the confined PMMA cylinders. Such polymer designs have potential applications in optoelectronic devices. This journal is

Monoamine oxidase inhibition by C4-substituted phthalonitriles

It was recently reported that a series of C5-substituted phthalimides are remarkably potent reversible inhibitors of recombinant human monoamine oxidase (MAO) B. Modeling studies suggested that the phthalimide ring forms numerous polar interactions with the polar region of the MAO-B substrate cavity while the C5 side chain extends to, and interacts via Van der Waals interactions with the hydrophobic regions of the enzyme entrance cavity. Interactions with both cavities appear to be requirements for high affinity binding. In the present study we have examined an analogs series of C4-substituted phthalonitriles as potential human MAO inhibitors. The phthalonitriles were found to be highly potent reversible MAO-B inhibitors with most analogs exhibiting IC50 values in the low nM range. The phthalonitriles also interacted with human MAO-A, although with lower binding affinities compared to MAO-B. Modeling studies suggest that the high binding affinities of the phthalonitriles to MAO-B may depend, at least in part, on the formation of polar interactions between the nitrile functional groups and the enzyme substrate cavity. Examination of a homologs series of benzonitriles established that the phthalonitrile moiety is more optimal for MAO-B inhibition than the corresponding benzonitrile moiety, and that C3-substituted benzonitriles are better MAO-B inhibitors than C4-substituted benzonitriles. Since elimination of the nitrile functional group yielded compounds with only moderate MAO-B inhibition potencies, it may be concluded that this functional group is privileged for MAO-B inhibition.

Inhibition of monoamine oxidase by C5-substituted phthalimide analogues

Literature reports that isatin as well as C5- and C6-substituted isatin analogues are reversible inhibitors of human monoamine oxidase (MAO) A and B. In general, C5- and C6-substitution of isatin leads to enhanced binding affinity to both MAO isozymes compared to isatin and in most instances result in selective binding to the MAO-B isoform. Crystallographic and modeling studies suggest that the isatin ring binds to the substrate cavities of MAO-A and -B and is stabilized by hydrogen bond interactions between the NH and the C2 carbonyl oxygen of the dioxoindolyl moiety and water molecules present in the substrate cavities of MAO-A and -B. Based on these observations and the close structural resemblances between isatin and its phthalimide isomer, a series of phthalimide analogues were synthesized and evaluated as MAO inhibitors. While phthalimide and N-aryl-substituted phthalimides were found to be weak MAO inhibitors, phthalimide homologues containing C5 substituents were potent reversible inhibitors of recombinant human MAO-B with IC50 values ranging from 0.007 to 2.5 μM and moderately potent reversible inhibitors of recombinant human MAO-A with IC50 values ranging from 0.22 to 9.0 μM. By employing molecular docking the importance of hydrogen bonding between the active sites of MAO-A and -B and the phthalimide inhibitors are highlighted.

Expeditious synthesis of glycosylated phthalocyanines

3,4-Dicyanophenyl O- and S-glycosides in the gluco, galacto, lacto, and cellobiose series were prepared in virtually quantitative yield through nucleophilic aromatic substitution of 4-nitrophthalonitrile with acetyl-protected glycoses and 1-thio-glycoses. Similarly, 2-(3,4-dicyanophenoxy) ethyl 2,3,4,6-tetra-O-acetyl-β-D-gluco- and galacto-pyranosides were obtained by nucleophilic substitution of 2-(tosyloxy)ethyl 2,3,4,6-tetra-O- acetyl-β-D-gluco- and -galactopyranoside with 3,4-dicyanophenol in 82% and 94% yields, respectively. All glycosides were deacetylated and tetramerized to the corresponding glycosylated zinc(II) phthalocyanines without further purification using a template condensation in 42-54% yields. Georg Thieme Verlag Stuttgart.