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Anthralini-fused ring derivatives and synthesis method thereof

A synthesis method and derivative technology, applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., to achieve the effects of simple operation, mild reaction conditions, and excellent yield

Inactive Publication Date: 2013-03-20
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As shown in formula A(b-h), it is a representative anthralin derivative with anti-psoriasis drug effect, and most derivatives still have obvious side effects

Method used

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  • Anthralini-fused ring derivatives and synthesis method thereof
  • Anthralini-fused ring derivatives and synthesis method thereof
  • Anthralini-fused ring derivatives and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Fischer chromium carbene and anthralin react in toluene at a ratio of 1:1

[0049]In a 25mL Schlenk reaction flask, add 1-phenylethynyl Fischer chromium carbene compound (1a) (175mg, 0.5mmol), anthralin (2) (114mg, 0.5mmol), N 2 Replace three times, inject 5 mL of toluene and 104 μL (0.75 mmol) of triethylamine, and stir at room temperature for 1 h. Separation and purification by column chromatography, the chromatographic column is a silica gel column, and the eluent is petroleum ether (boiling range 30-60°C) / dichloromethane (v / v, 2:1, 1:1 gradient change), according to the flow out sequence Sequentially collect orange-red and green components successively, obtain compound (3) respectively after removing solvent [(48mg, yield is 25%, R f =0.5, petroleum ether (boiling range 30-60°C) / dichloromethane (v / v, 2:1); high-resolution mass spectrometry confirmed the product, x-ray crystallography confirmed the absolute configuration of the product, and NMR verified t...

Embodiment 2

[0050] Example 2: Fischer tungsten carbene and anthralin react in toluene at a ratio of 1:1

[0051] In a 25mL Schlenk reaction flask, add 1-phenylethynyl Fischer chromium carbene compound (1b) (241mg, 0.5mmol), anthralin (2) (114mg, 0.5mmol), N 2 Replaced three times, injected 5 mL of toluene and 104 μL (0.75 mmol) of triethylamine, and stirred at room temperature for 3.5 h. Separation and purification by column chromatography, the chromatographic column is a silica gel column, the eluent is petroleum ether (boiling range 30-60°C) / dichloromethane (v / v, 1:1), the orange-red components are collected, and after removing the solvent Obtain product (3) [(88mg, yield is 46%, R f =0.4, sherwood oil (boiling range 30~60 ℃) / dichloromethane (v / v, 2:1); NMR verification compound purity>95% (same as Example 1), its high-resolution mass spectrum and NMR data are listed in After the examples].

Embodiment 3

[0052] Example 3: Fischer chromium carbene reacts with anthralin at a ratio of 5:1 in dichloromethane

[0053] In a 25mL Schlenk reaction flask, add 1-phenylethynyl Fischer chromium carbene compound (1a) (578mg, 1.65mmol), anthralin (2) (74mg, 0.33mmol), N 2 Replaced three times, injected 5 mL of dichloromethane and 75 μL (0.5 mmol) of triethylamine, and stirred at room temperature for 19 h. Separation and purification by column chromatography, the chromatography column is a silica gel column, and the eluent is petroleum ether (boiling range 30-60°C) / dichloromethane (v / v, 5:1, 3:1, 1:1 gradient change) , collect brown-green, brown and green three components successively according to the order of flowing out, obtain product (4a) respectively after removing solvent [(134mg, yield is 33%, R f =0.6, petroleum ether (boiling range 30~60°C) / dichloromethane (v / v, 2:1); NMR and elemental analysis verify compound purity>95%], (5a)[(98mg, yield is 25% %,R f =0.5, petroleum ether (boi...

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Abstract

The invention discloses a method for synthesizing an important anti-psoriasis medicament anthralini-fused ring derivatives, and synthesizes a plurality of novel anthralini-fused ring derivatives. The method comprises the steps of taking anthralini (dihydroxy anthracene phenols, 1,8,9-dithranol) as an initial raw material, allowing the initial raw material to react with 1-phenylethynyl Fischer carbene compounds and obtaining four types of novel anthralini-fused ring derivatives through continuous addition / cyclization reaction and oxidation-demetalization reaction. The method utilizes the multi-reactivity of the 1-phenylethynyl Fischer carbene compounds and subjects the 1-phenylethynyl Fischer carbene compounds and anthralini to successive multi-step reaction under mild conditions so as to obtain the anthralini-fused ring derivatives which are difficult to synthesize by conventional organic synthesis methods or can be obtained only through complex synthesis steps. The method has the advantages of mild conditions of synthesis reaction, simple convenient operation, readily available raw materials and high efficiency.

Description

technical field [0001] The present invention relates to anthralinocyclic derivatives, in particular to anthralinocyclic derivatives and a synthesis method thereof. [0002] Background technique [0003] Anthralin as shown in formula A (a) is a kind of most widely used medicine for the treatment of psoriasis (Müller, K.; Reindl, H.; Breu, K.J.Med.Chem.2001,44,814-821 Gillberg, B.O.; Zetterberg, G.; Swanbeck, G. Nature 1967, 214, 415.). But anthralin has obvious side effects, and it can produce certain corrosivity to the normal skin tissue around the drug site and cause inflammation, which seriously limits its application (Farber, E.M.; Nall, L.Drugs 1984, 28, 324-346 .). Therefore, people have been studying various derivatives of anthralin for a long time, hoping to reduce side effects as much as possible while maintaining the efficacy. The root of the side effects of anthralin is the 10 CH 2 Oxygen free radicals will be produced to corrode normal skin, but the specific c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/755C07C45/61C07D311/02C07D493/04C07D493/06
Inventor 余正坤罗宁
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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