Diphenyltetrahydroporphin compound, preparation method and application thereof

A technology of diphenyltetrahydroporine and compound, applied in the field of diphenyltetrahydroporine compound and preparation thereof, can solve the problems of complex composition, weak absorption, difficult preparation and the like

Inactive Publication Date: 2018-11-23
陈聃烨
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to overcome the defects of existing photosensitive drugs such as complex composition, certain skin phototoxicity, difficult preparation, and weak absorption in the red light region, the present invention reduces the porphine compound and prepares the tetrahydroporphine compound , which enhances the compound’s absorption in the red light region; introduces polar groups around the compound, improves water solubility, increases the absorption and distribution of photosensitizers in tumor tissues, and reduces skin phototoxic side effects; the new compound has a stable structure; The preparation process is simple and easy

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 5,15-two [(3-carboxymethoxy) phenyl] tetrahydroporphine (1) synthetic preparation method

[0029]

[0030] 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. After 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, filtered with suction, and the filtrate was evaporated under reduced pressure to remove the solvent. The obtained residue was separated and purified by column chromatography to obtain diphenyltetrahydroporphine compound 3 (95.2 mg, 28....

Embodiment 2

[0033] The preparation method of 5,15-bis[(3-carboxypropoxy)phenyl]tetrahydroporphine (4)

[0034]

[0035] 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 monitors the complete reaction of raw materials. 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, filtered with suction, and the filtrate was evaporated under reduced pressure to remove the solvent. The resulting residue was separated and purified by column chromatography to obtain diphenyltetrahydroporphin compound 6 (125.3 mg, 34.5%).

[0036] Compound 6 (363 mg, ...

Embodiment 3

[0038] The preparation method of 5,15-bis[(3-carboxymethoxy-4-methoxy)phenyl]tetrahydroporphine (7)

[0039]

[0040] 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 monitors the complete reaction of raw materials. 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 HCl solution (2mol / L), and let stand to separate the layers. The organic phase was washed with saturated brine (50 mL×3), dried over anhydrous sodium sulfate, filtered with suction, and the filtrate was evaporated under reduced pressure to remove the solvent. The resulting residue was separated and purified by column chromatography to obtain diphenyltetrahydroporphin compound 9 (96.8 mg, 26.5%).

[0041] Compound 9 (365 mg,...

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Abstract

The invention relates to a diphenyltetrahydroporphin compound, a preparation method and application thereof. The compound has the following structure (I) which is shown in the description, wherein R1and R2 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 fieldsof photosensitive drugs (also called as a photosensitizer or photodynamic drug) and photodynamic therapy, and particularly relates to a diphenyltetrahydroporphin photosensitizer, a preparation methodand application in the field of medicines. The diphenyltetrahydroporphin compound prepared by the method provided by the inventionvis stable in chemical property, has strong photodynamic activity, andcan 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 diphenyltetrahydroporphine compounds and a preparation method and application thereof. 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. After absorbing the photon energy, the photosensitizer changes from the ground state to an unstable In the e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00A61P35/00A61P27/02A61P17/00A61P17/12A61P31/20
CPCA61K41/0071A61P17/00A61P17/12A61P27/02A61P31/20A61P35/00C07D487/22
Inventor 陈聃烨高迎华严懿嘉廖平永
Owner 陈聃烨
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