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Benzimidazolyl zinc porphyrin, benzimidazolyl porphyrin and synthesis method thereof

A technology of benzimidazolyl porphyrin and benzimidazolyl zinc, applied in the field of chemical synthesis, can solve the problems such as insufficient variety of porphyrin and its metal complexes

Active Publication Date: 2021-02-02
LANGFANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The existing porphyrins and their metal complexes are not rich enough, and they can no longer meet the increasingly changeable conditions of the human body in the field of medicine. Therefore, it is necessary to provide a metalloporphyrin compound with a functional group that can target the increasingly changeable conditions of the human body. Become a technical problem in the field of chemical synthesis

Method used

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  • Benzimidazolyl zinc porphyrin, benzimidazolyl porphyrin and synthesis method thereof
  • Benzimidazolyl zinc porphyrin, benzimidazolyl porphyrin and synthesis method thereof
  • Benzimidazolyl zinc porphyrin, benzimidazolyl porphyrin and synthesis method thereof

Examples

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Embodiment 1

[0054] This embodiment provides a kind of benzimidazolyl porphyrin, its specific name is 5-(4-benzimidazolyl) phenyl-10,15,20-triphenylporphyrin, and its structural formula is as follows:

[0055]

[0056] The preparation method of above-mentioned benzimidazolyl porphyrin is:

[0057] S1: Synthesis of 5-p-carboxyphenyl-10,15,20-triphenylporphyrin

[0058] Add 1.211g (0.008mol) p-formylbenzoic acid, 2.967g (0.031mol) distilled benzaldehyde and 150mL propionic acid to a 250mL three-necked flask equipped with a mechanical stirrer, reflux condenser, drying tube, and thermometer. After reflux, a mixed solution of 2.65 mL (0.04 mol) of pyrrole and 8.16 mL of propionic acid was slowly added dropwise to the solution. After the dropwise addition, continue to reflux for 30 min to stop the reaction. After cooling, add 50mL of absolute ethanol and keep at 1°C for 8h. Suction filtration, wash the filter cake with absolute ethanol to obtain purple crystals. Silica gel column chromato...

Embodiment 2

[0067] This embodiment provides a benzimidazole-based porphyrin whose specific name and structural formula are the same as those of the corresponding compound in Example 1. The preparation method is as follows:

[0068] S1: Synthesis of 5-p-carboxyphenyl-10,15,20-triphenylporphyrin

[0069] Add 1.514g (0.01mol) p-formylbenzoic acid, 3.519g (0.033mol) distilled benzaldehyde and 150mL propionic acid to a 250mL three-necked flask equipped with a mechanical stirrer, reflux condenser, drying tube, and thermometer. After reflux, a mixed solution of 2.98 mL (0.045 mol) of pyrrole and 8.16 mL of propionic acid was slowly added dropwise to the solution. After the dropwise addition, continue to reflux for 45 minutes to stop the reaction. After cooling, add 80mL of absolute ethanol and keep at 15°C for 10h. Suction filtration, wash the filter cake with absolute ethanol to obtain purple crystals. Silica gel column chromatography, using chloroform as eluent to wash away the first color ...

Embodiment 3

[0076] This embodiment provides a kind of benzimidazolyl porphyrin, its specific name and structural formula are all identical with embodiment 1, and preparation method is as follows:

[0077] S1: Synthesis of 5-p-carboxyphenyl-10,15,20-triphenylporphyrin

[0078] Add 1.816g (0.012mol) p-formylbenzoic acid, 3.35g (0.035mol) distilled benzaldehyde and 150mL propionic acid to a 250mL three-necked flask equipped with a mechanical stirrer, reflux condenser, drying tube, and thermometer. After reflux, a mixed solution of 3.31 mL (0.05 mol) of pyrrole and 8.16 mL of propionic acid was slowly added dropwise to the solution. After the dropwise addition, continue to reflux for 60 min to stop the reaction. After cooling, add 100mL of absolute ethanol and keep at 15°C for 12h. Suction filtration, wash the filter cake with absolute ethanol to obtain purple crystals. Silica gel column chromatography, using chloroform as eluent to wash away the first color band; then using chloroform: et...

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Abstract

The application discloses a benzimidazolyl zinc porphyrin, a benzimidazolyl porphyrin and a synthesis method thereof, wherein the structural formula of the benzimidazolyl zinc porphyrin is as follows. This application provides a new type of benzimidazole-based porphyrin, benzimidazole-based zinc porphyrin and its synthesis method, which enriches the types of benzimidazole-based porphyrin and benzimidazole-based zinc porphyrin, and provides porphyrin anti-cancer Drug development provides a new direction. Through experiments, we believe that the benzimidazolyl zinc porphyrin provided by the present application has good application in antibacterial, antioxidation, antitumor, anticancer and other aspects.

Description

technical field [0001] The application belongs to the technical field of chemical synthesis, and in particular relates to a benzimidazolyl porphyrin, a benzimidazolyl zinc porphyrin and a synthesis method thereof. Background technique [0002] Porphine is composed of 20 carbon atoms and contains 18 π-electron planar conjugated macrocyclic compounds. Porphyrin is a kind of macrocyclic tetrapyrrole system compound with porphine ring as the parent skeleton and aromatic properties. The ring contains 8 β-positions and 4 meso-positions ( figure 1 5, 10, 15, 20 in ), the hydrogen atoms at these positions can all undergo substitution reactions with other groups, thus forming a free porphyrin ring. The 4 N atoms in the ring contain lone pairs of electrons, which can interact with metal ions Coordination reactions form metalloporphyrins. The porphine ring structure is as follows: [0003] [0004] As a special macrocyclic aromatic system, porphyrin and its metal complexes are wi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22A61P35/00
CPCA61P35/00C07D487/22
Inventor 彭晓霞
Owner LANGFANG NORMAL UNIV