Substituted aryl tetracyclic antifungal compound as well as preparation method and application thereof

A compound, tetracyclic technology, applied in the field of medicine, can solve the problems of antifungal activity and antifungal spectrum to be improved, poor solubility and the like

Active Publication Date: 2013-08-21
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the solubility of Sampangine is very poor, and the a

Method used

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  • Substituted aryl tetracyclic antifungal compound as well as preparation method and application thereof
  • Substituted aryl tetracyclic antifungal compound as well as preparation method and application thereof
  • Substituted aryl tetracyclic antifungal compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Example 1: Preparation of (E)-2-((E)-but-2-ene-ylidene)-1,1-dimethylhydrazine (Ⅲ)

[0086] Dissolve (Z)-but-2-enal (7.1g, 0.1mol) in 100mL of anhydrous THF, and slowly add unsymmetrical dimethylhydrazine (6.0g, 0.1mol, 1.0eq) dropwise. After the dropwise addition, the reaction solution was stirred overnight at room temperature. The reaction mixture was concentrated to dryness to obtain 9.8 g of light brown liquid with a yield of 87.5%. 1 H NMR (400MHz, CDCl 3 )δppm:6.96(d,J=8.8Hz,1H),6.12-6.18(dd,J=8.8,12.6Hz,1H),5.73-5.79(m,1H),2.76(s,6H),1.77(d ,J=6.8Hz,3H).

Embodiment 2

[0087] Example 2: Preparation of 4,6-dibromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-ol (Ⅴ)

[0088] Dissolve 1 g of the raw material 2,2-dimethyl-2,3-dihydrobenzofuran-7-ol (IV) (6.0 mmol) in chloroform (35 mL) and cool to 0°C. Liquid bromine (1g, 15mmol, 2.5eq) was slowly added dropwise. After removing the ice bath, react at room temperature for 2 hours. After concentration and removal of the solvent, a brown solid was obtained. After column chromatography (dichloromethane as eluent), 1.4 g of the product was obtained, with a yield of 67.3%. 1 H NMR (400MHz, CDCl 3 )δppm: 6.98(s,1H), 4.99(br s,1H), 3.00(s,2H), 1.44(s,6H).

Embodiment 3

[0089] Example 3: Preparation of 6-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-4,7-dione (Ⅵ)

[0090]Dissolve 470 mg of chromium trioxide (4.7 mmol) in water (5 mL). This solution was added dropwise to a volume ratio of 7 containing 4,6-dibromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-ol (Ⅴ) (500mg, 1.6mmol): 2 in acetic acid-water solution (23mL). After reacting for 1 hour, add 50 mL of water to dilute, and extract 3 times with ethyl acetate. The organic phases were combined, dried and concentrated to obtain a crude product. After silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 1:5), 220 mg of red powdery compound was obtained, with a yield of 52%. 1 HNMR (400MHz, CDCl 3 )δppm: 7.01(s,1H), 2.85(s,2H), 1.49(s,6H).

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Abstract

The invention relates to the technical field of pharmaceuticals, and provides a substituted aryl tetracyclic antifungal compound and pharmaceutically acceptable salts. The substituted aryl tetracyclic antifungal compound is as shown in a structural formula of the description. The invention further provides a preparation method of the compound and an application of the compound in preparing antifungal medicaments.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a novel substituted aromatic tetracyclic compound—aryl (hetero)cycloquinoline dione and its salts, a preparation method, and an application as an antifungal drug. Background technique [0002] In recent years, factors such as the abuse of antibiotics, tumor radiotherapy and chemotherapy, and organ transplantation have caused immunosuppression. In addition, the number of AIDS patients has increased rapidly. Infection has become the main cause of death from major diseases such as AIDS and cancer. However, clinically ideal antifungal drugs are lacking. Polyene antibiotics (such as amphotericin B) that act on fungal cell membrane lipids are the first choice for treatment, but their clinical application is severely limited due to their severe side effects. Azole drugs (such as fluconazole, itraconazole, and voriconazole) that act on lanosterol 14α-demethylase (CYP51) are currently ...

Claims

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Application Information

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IPC IPC(8): C07D471/16C07D495/16C07D491/16A61K31/4745A61K31/496A61P31/10
Inventor 盛春泉张万年江志赶谌卫董国强缪震元姚建忠
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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