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Novel hematoporphyrin monofluoroalkyl diether and fluorophenyl alkyl diether derivatives and application thereof in field of medicines

A technology of hematoporphyrin fluorophenyl alkyl diether and hematoporphyrin monofluoroalkyl diether, which can be used in pharmaceutical formulations, medical preparations containing active ingredients, antitumor drugs, etc., and can solve the problem of unreported Compound pharmacological activity, etc.

Pending Publication Date: 2020-10-27
SHANGHAI XIANHUI MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Fukuda Rongsan, Otani Takusan and others reported polyfluorinated or perfluorinated alkyl ether derivatives of hematoporphyrin in the patent (JP19860088799), but the patent did not report the pharmacological activity of these compounds

Method used

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  • Novel hematoporphyrin monofluoroalkyl diether and fluorophenyl alkyl diether derivatives and application thereof in field of medicines
  • Novel hematoporphyrin monofluoroalkyl diether and fluorophenyl alkyl diether derivatives and application thereof in field of medicines
  • Novel hematoporphyrin monofluoroalkyl diether and fluorophenyl alkyl diether derivatives and application thereof in field of medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] 3,8-bis(1-(2-fluoroethoxy)ethyl) hypoporphyrin (I 1 ) preparation:

[0094]

[0095]Add protoporphyrin dimethyl ester (614mg, 1.041mmol) into the round bottom flask, then add hydrogen bromide / acetic acid solution (7mL) with a content of about 30%, stir at room temperature for about 36h, after TLC monitors that the reaction is complete, depressurize Remove the solvent by distillation; add 2-fluoroethanol (3 mL) to the residual solid to dissolve it, stir at room temperature for 4 h, add ethyl acetate (EA) to dilute after the reaction, wash with water four times, and remove the solvent by distillation under reduced pressure; (THF, 8mL) to dissolve the residue, add NaOH solution (2M, 3mL) and stir at room temperature for 2h, add water (50mL) to dilute, and add dilute hydrochloric acid solution (2M, 3mL) to adjust the pH to weak acidity, wash with ethyl acetate (50mL ×3) extraction, washed with saturated sodium chloride solution (50mL×3), dried over anhydrous sodium sulf...

Embodiment 2

[0097] 3,8-bis(1-(3-fluoropropoxy)ethyl) hypoporphyrin (I 2 ) preparation:

[0098]

[0099] Compound I 1 The synthetic method prepared compound I 2 . 1 H NMR (400MHz, Pyr-d 5 )δppm: 10.96(s, 1H), 10.89(d, J=10.0Hz, 2H,), 10.39(s, 1H,), 6.29(s, 2H,), 4.69(s, 4H,), 3.94(s ,4H,),3.69(s,12H,),3.65(s,4H,),2.36(s,6H,),1.36-1.19(m,8H,),-3.03(s,2H,). 13 CNMR (101MHz, Pyr-d 5 )δppm:176.92,174.67,151.66,151.01,150.60,137.31,136.91,136.67,136.28,125.28,124.93,124.69,124.25,100.65,100.40,100.10,99.33,99.03,83.90,82.28,75.19,66.64,39.23,33.41 ,33.09,32.90,31.27,30.89,26.86,24.23,23.82,22.69,15.57,14.12,14.07,12.94,12.91,12.81,12.76. 19 F NMR (377MHz, DMSO-d 6 )δppm: 17.66(s).MS(MALDI TOF)(DART Positive):m / z calcd for C 40 h 48 f 2 N 4 o 6 [M+H] + , 719.6; found, 719.6.

Embodiment 3

[0101] 3,8-bis(1-(4-fluorobutoxy)ethyl) hypoporphyrin (I 3 ) preparation:

[0102]

[0103] Compound I 1 The synthetic method prepared compound I 3 . 1 H NMR (400MHz, Pyr-d 5 )δppm: 11.00(s,1H,),10.94(s,1H,),10.89(s,1H,),10.40(s,1H,),6.27(s,2H,),4.69(s,4H,) ,4.51(s,2H,),4.39(s,2H,),3.83(s,2H,),3.78–3.69(m,12H,),3.67(s,2H,),3.64(s,4H,) ,2.37(s,6H,),1.95(s,4H,),-3.02(s,2H,). 13 CNMR (101MHz, Pyr-d 5 )δppm:175.39,150.17,149.08,139.72,135.78,135.38,135.14,134.76,123.76,123.64,123.41,123.17,122.73,99.04,98.71,97.49,96.25,84.75,83.12,73.50,68.79,37.70,27.87,27.68 ,26.22,25.41,22.30,11.45,11.40,11.34,11.26. 19 F NMR (377MHz, Pyr-d 5 )δppm: -216.99(d,J=24.5Hz),-217.08(s),-217.12--217.34(m).MS(MALDI TOF)(DART Positive):m / z calcdfor C 42 h 52 f 2 N 4 o 6 [M+H] + ,746.8; found, 746.8.

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Abstract

The invention relates to novel hematoporphyrin monofluoroalkyl diether (I) and fluorophenyl alkyl diether derivatives (II) and application thereof in the field of medicines. The compound has the following structure. The invention relates to the field of photosensitive drugs and photodynamic therapy, in particular to novel hematoporphyrin monofluoroalkyl diether and fluorophenyl alkyl diether derivatives and application thereof in the field of medicines. The prepared compound is single in component, stable in property, controllable in quality, simple and convenient in preparation method and relatively good in photodynamic activity, and can be used as a photodynamic therapy drug for diseases such as tumors, retinal macular degeneration, actinic keratosis, nevus flammeus and condyloma acuminatum.

Description

technical field [0001] The invention relates to photosensitizing drugs and photodynamic therapy, in particular to a class of novel hematoporphyrin monofluoroalkyl diether and fluorophenyl alkyl diether derivatives and their application in the medical field. Background technique [0002] Photodynamic therapy (PDT), as a new method for the treatment of tumors, macular degeneration, actinic keratosis, port wine stains, condyloma acuminatum and other diseases (Chem. Rev. 2019, 119, 797-828), has been clinically Remarkable achievements have been made in the treatment. The mechanism is that after the photosensitizer enters the body, it selectively gathers in the target tissue along with the blood circulation, and then irradiates the target tissue with a laser of a certain wavelength to generate active oxygen (such as singlet oxygen) Act on target cells, causing cell metabolism disorder, thereby killing target cells. [0003] In photodynamic therapy, photosensitizing drugs (also k...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61P35/00A61P27/02A61P17/00A61P17/12A61P31/20
CPCC07D487/22A61K41/0071A61K41/0076A61P35/00A61P27/02A61P17/00A61P17/12A61P31/20
Inventor 陈志龙李慢一严懿嘉张嘉辉朱雪雪高迎华山妮妮坎敏敏王来兴韩一平江颖马大福奧多纳邱彦金辉吴晓锋阮继武陈婷刘世芳张洪涛糜乐
Owner SHANGHAI XIANHUI MEDICAL TECH
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