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Application of polycyclic aryl compound in preparation of antifungal drugs

An antifungal drug and polycyclic aromatic group technology, which is applied in antifungal agents, drug delivery, and resistance to vector-borne diseases, etc., can solve the problems of antibacterial drug resistance, limited drug selection, and low bioavailability, and achieve The effect of low toxicity

Active Publication Date: 2022-01-21
THE FIRST AFFILIATED HOSPITAL OF JINAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs have their own advantages and disadvantages. Although azoles have high safety and oral bioavailability, their antibacterial effects lead to serious drug resistance; Acute kidney injury occurs in % of adults treated with amphotericin B, leading to significant increases in mortality, length of hospital stay, and costs; echinocandins are a new class of antifungal drugs approved in 30 years, but oral bioavailability low rate
Therefore, the choice of drugs for the treatment of deep fungal infections is limited, unable to meet the growing clinical needs, and there is an urgent need to develop new antifungal drugs

Method used

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  • Application of polycyclic aryl compound in preparation of antifungal drugs
  • Application of polycyclic aryl compound in preparation of antifungal drugs
  • Application of polycyclic aryl compound in preparation of antifungal drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The synthesis of embodiment 1 compound 1-3

[0034]

[0035] Compound 1-1 (5.00g, 21.8mmol, 1.00eq) was dissolved in dichloromethane (25mL) at room temperature, and then compound 1-2 (3.54g, 26.2mmol, 3.13mL, 1.20eq) was added. After stirring and reacting for 12 hours, the reaction solution was filtered and concentrated to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (DCM:MeOH=8:1) to obtain white solid compound 1-3.

[0036] Compounds 1-3: 1 H-NMR (400MHz, CDCl 3 ), δ7.42(s,1H),7.34-7.30(t,J=7.8Hz,2H),7.16(s,1H),7.14-7.10(t,J=7.6Hz,2H),4.91(s, 1H) 3.83-3.80(t, J=4.8Hz, 4H), 3.22-3.21(d, J=5.2Hz, 2H), 2.50-2.46(m, 6H), 1.45(s, 9H); LC-MS m / z.

Embodiment 2

[0037] The synthesis of embodiment 2 compound 1-4

[0038]

[0039] Compound 1-3 (12.0g, 32.9mmol, 1.00eq) was dissolved in methanol (60.0mL), and hydrochloric acid methanol solution (32.9mmol, 48.0mL, 1.00eq) was added at zero temperature. Subsequently, the reaction was raised to normal temperature for reaction. After reacting for 16 hours, the reaction solution was concentrated under reduced pressure to obtain crude hydrochloride compound 1-4 (13.1 g) as a white solid.

[0040] Compound 1-4: LC-MS m / z 265.2[M+H] + .

Embodiment 3

[0041] The synthesis of embodiment 3 compound 1-6

[0042]

[0043] At room temperature, compound 1-5 (8.00g, 35.9mmol, 1.00eq) was dissolved in N,N-dimethylformamide (100mL), and then N,N-dimethylformamide dimethyl acetal was added (35.9 g, 301 mmol, 40.0 mL, 8.38 eq). After stirring and reacting for 2 hours, the reaction solution was filtered to obtain a filtrate. The filtrate was spin-dried and concentrated under reduced pressure to obtain light yellow solid compound 1-6 (8.50 g, 30.6 mmol, yield 85.2%).

[0044] Compounds 1-6: 1 H NMR (400MHz, CDCl 3 ),δ8.08(s,1H),7.32-7.30(m,2H),7.19-7.17(d,J=8.4Hz,2H),3.43(s,3H),3.37-3.32(m,1H), 3.22(s,3H),2.77-2.62(m,4H); LC-MS m / z 278.1[M+H] + .

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Abstract

The invention provides a polycyclic aryl compound S1 for preparing antifungal infection drugs. The structural formula of the polycyclic compound is S1. The polycyclic aryl compound with the core-shell structure and shown in S1 is suitable for preparing drugs for resisting infection of pathogenic fungi such as candida, aspergillus and mucor, and has the following beneficial effects that the compound S1 has a broad-spectrum antifungal effect on the pathogenic fungi including but not limited to the candida, the aspergillus and the mucor, and is effective on azole drug-resistant candida, meanwhile, toxicity to mammals is low, systemic fungal infection can be treated through oral administration, and mucous film candida infection can be treated through local application.

Description

technical field [0001] The present invention belongs to the field of medicine. More specifically, the present invention relates to the application of a polycyclic aryl compound S1 in the preparation of drugs against pathogenic fungi represented by Candida, Aspergillus, Mucor and Cryptococcus. Background technique [0002] Fungal infection is a serious threat to the healthy life of human beings. According to the parts that invade the human body, fungal infection can be divided into superficial mycosis and deep mycosis. The main pathogens of the latter are conditional pathogens represented by Candida, Aspergillus, Mucor and Cryptococcus Fungi, which cause more than 13 million infections and 1.6 million deaths each year, surpass the deaths from malaria, tuberculosis and breast cancer. What's more serious is that even with standard antifungal therapy, the mortality rate is as high as 67% in immunosuppressed patients. [0003] At present, deep fungal infection is mainly treated...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/194A61K31/496A61K9/00A61P31/10
CPCC07D295/194A61K9/0053A61K9/0019A61P31/10Y02P20/55Y02A50/30
Inventor 张宏叶文才张艺山胡利军李水秀赵亚婧翁泺棓
Owner THE FIRST AFFILIATED HOSPITAL OF JINAN UNIV
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