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Diphenyldihydroporphin compound, preparation method and application thereof

A diphenyl chlorin compound technology, applied in the field of diphenyl chlorin compound and its preparation, can solve the problems of skin phototoxicity, unstable structure, complex composition, etc., to reduce phototoxicity Side effects, enhanced photodynamic effects, increased absorption and distribution effects

Inactive Publication Date: 2018-11-23
陈志龙
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to overcome the defects of complex composition, unstable structure, difficult preparation, skin phototoxicity, and weak absorption in the red light region existing in existing photosensitive drugs, the present invention reduces the porphine compound and prepares a new dihydro Porphine compound enhances the absorption of the compound in the red light region; a polar group is introduced around the compound, which improves the water solubility, increases the absorption and distribution of the photosensitizer in the tumor, strengthens the photodynamic effect and reduces the Phototoxicity and side effects; the structure of the new compound is stable; the preparation process is simple and easy

Method used

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  • Diphenyldihydroporphin compound, preparation method and application thereof
  • Diphenyldihydroporphin compound, preparation method and application thereof
  • Diphenyldihydroporphin compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 5,15-two [(3-carboxymethoxy) phenyl] chlorin (1) synthetic preparation method

[0028]

[0029] Compound 2 (333mg, 0.5mmol) and potassium carbonate (828mg, 6mmol) were added to pyridine (23mL), stirred, and heated to reflux under nitrogen protection; a pyridine solution of p-toluenesulfonyl hydrazide (0.5mol / L) was added dropwise , Thin-layer chromatography (TLC) monitored until the reaction was complete. The reaction solution was cooled, ethyl acetate (100 mL) and distilled water (50 mL) were added, and heated to reflux for 1 h. Cool, neutralize with hydrochloric acid solution (2mol / L), and let stand to separate layers. The organic phase was washed with saturated brine (50 mL×3), dried over anhydrous sodium sulfate, and filtered with suction. The filtrate was stirred at normal temperature, and chlorobenzoquinone was added in batches until the characteristic absorption peak in the ultraviolet-visible spectrum of diphenyltetrahydroporphin compound disappeared; ), 2...

Embodiment 2

[0032] The preparation method of 5,15-bis[(3-carboxypropoxy)phenyl]chlorin (4)

[0033]

[0034] Compound 5 (361mg, 0.5mmol) and potassium carbonate (828mg, 6mmol) were added to pyridine (23mL), stirred, and heated to reflux under nitrogen protection; a pyridine solution of p-toluenesulfonylhydrazide (0.5mol / L) was added dropwise , TLC monitored until the reaction was complete. The reaction solution was cooled, ethyl acetate (100 mL) and distilled water (50 mL) were added, and heated to reflux for 1 h. Cool, neutralize with hydrochloric acid solution (2mol / L), and let stand to separate layers. The organic phase was washed with saturated brine (50 mL×3), dried over anhydrous sodium sulfate, and filtered with suction. The filtrate was stirred at normal temperature, and chlorobenzoquinone was added in batches until the characteristic absorption peak in the ultraviolet-visible spectrum of diphenyltetrahydroporphin compound disappeared; ), 2M sodium hydroxide solution (50mL×3...

Embodiment 3

[0037] The preparation method of 5,15-bis[(3-carboxymethoxy-4-methoxy)phenyl]chlorin (7)

[0038]

[0039] Compound 8 (363mg, 0.5mmol) and potassium carbonate (828mg, 6mmol) were added to pyridine (23mL), stirred, and heated to reflux under nitrogen protection; a pyridine solution of p-toluenesulfonyl hydrazide (0.5mol / L) was added dropwise , TLC monitored until the reaction was complete. The reaction solution was cooled, ethyl acetate (100 mL) and distilled water (50 mL) were added, and heated to reflux for 1 h. Cool, neutralize with hydrochloric acid solution (2mol / L), and let stand to separate layers. The organic phase was washed with saturated brine (50 mL×3), dried over anhydrous sodium sulfate, and filtered with suction. The filtrate was stirred at normal temperature, and chlorobenzoquinone was added in batches until the characteristic absorption peak in the ultraviolet-visible spectrum of diphenyltetrahydroporphin compound disappeared; ), 2M sodium hydroxide solut...

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Abstract

The invention relates to a diphenyldihydroporphin compound, a preparation method and application thereof. The compound has the following structure (I) which is shown in the description, wherein R1 andR2 are positioned at the ortho-position (o-), meta-position (m-) or para-position (p-) of a benzene ring; R1 is -H or -OMe; R2 is -OCH2COOH or -OCH2CH2CH2COOH. The invention relates to the fields ofphotosensitive drugs (also called as a photosensitizer or photodynamic drug) and photodynamic therapy, and particularly relates to a diphenyldihydroporphin photosensitizer, a preparation method and application in the field of medicines. The diphenyldihydroporphin compound prepared by the method provided by the invention is stable in chemical property, has strong photodynamic activity, and can be used as a drug for photodynamic diagnosis and treatment of diseases such as tumors, macula-retinae degeneration, actinic keratosis, nevus flammeus and condyloma acuminata and the like.

Description

technical field [0001] The invention relates to the field of photosensitizing drugs and photodynamic therapy, in particular to a class of diphenyl chlorin compound and its preparation method and application. Background technique [0002] Compared with traditional surgical treatment, chemotherapy, radiotherapy, etc., photodynamic therapy (PDT) is characterized by its good selectivity, low toxic and side effects, good reproducibility, safety, minimal invasiveness, synergy and relatively low cost. Advantages such as, are more and more favored by doctors and patients; Show huge potential and strong vitality. The principle of photodynamic therapy is that after the photosensitizer enters the body, it selectively gathers in the target tissue along with the blood circulation, and then directly irradiates the tumor tissue with a laser of a certain wavelength to generate free radicals with high oxidative activity (such as singlet oxygen). , act on target cells, cause cell metabolism ...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61P35/00A61P27/02A61P17/00A61P17/12A61P31/20
CPCA61K41/0071A61P17/00A61P17/12A61P27/02A61P31/20A61P35/00C07D487/22
Inventor 陈志龙朱维高迎华廖平永吴晓锋王来兴阮氏芳英代伏·马格替克严懿嘉
Owner 陈志龙
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