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Preparation method and anti-pulmonary fibrosis application of benzopyran compound

A technology for benzopyran compounds and pulmonary fibrosis, which is applied in the field of natural medicinal chemistry, can solve problems such as no benzopyran compounds reported in literature, achieve good market application and promotion prospects, and have low toxicity effects

Active Publication Date: 2015-10-14
上海盛通康维药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Genetic engineering strain CGMCC NO. 5675 is Streptomyces xiamenensis carrying rifamycin and streptomycin resistance, and there is no literature report on the isolation of benzopyran compounds from this strain

Method used

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  • Preparation method and anti-pulmonary fibrosis application of benzopyran compound
  • Preparation method and anti-pulmonary fibrosis application of benzopyran compound
  • Preparation method and anti-pulmonary fibrosis application of benzopyran compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1, separation and purification of benzopyran compound

[0034]Take the S.xiamenensis M6 strain (i.e. Streptomyces xiamenensis CGMCC NO.5675) for liquid fermentation culture (30 liters) for 7 days. After centrifugation, the supernatant was extracted three times with ethyl acetate, and the residue was extracted with an equal volume of Ethyl acetate: methanol: formic acid = 80:15:5 (volume ratio) mixed solvent extraction 3 times, 12 hours each time. The extracts were combined and concentrated to obtain 13.4 g of the total extract. Get the total extract and dissolve it with an appropriate amount of chloroform-methanol mixed solvent, add 10 grams of 200-300 mesh silica gel G (product of Qingdao Ocean Chemical Group Co., Ltd.) - methanol (100:1, 70:1, 60:1, 50:1, 30:1, 15:1, 10:1, 5:1, 2:1, 1:1, (volume ratio) to methanol] Gradient elution, the flow rate is 15 seconds / drop, 150-100 ml / bottle receiving, the polarity of the elution solvent is gradually increased by...

Embodiment 2

[0039] Example 2. Benzopyran Compounds Inhibit the Proliferation and Viability of Human Lung Fibroblasts

[0040] The materials are as follows:

[0041] Cells: Human lung fibroblasts (human lung fibroblasts, W126 cells); Drugs: Compound 1 (Xiamenmycin C) and Compound 2 (Xiamenmycin) obtained from the above examples Among them, compound 1 was used as the drug-treated experimental group, and compound 2 was used as the drug-treated comparison group.

[0042] Method: WI26 cells grown to 70-80% confluent were digested with 0.25% trypsin and seeded in 96-well plate, 1×10 per well. 3 cells. After 24 hours, the medium was changed and drugs were added. The final concentration of compound 1 in the drug treatment experimental group was 15 μg / ml, and the solvent DMSO concentration was 1 / 1000. The control group was DMSO, and the final concentration was 1 / 1000. The final concentration of compound 2 in the drug treatment control group was 30 μg / ml, and the solvent DMSO concentration was ...

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Abstract

The invention discloses a preparation method of a benzopyran compound and an anti-pulmonary fibrosis application. The structural formula of benzopyran compound is as follows: wherein, R1 is selected from hydrogen, C1~C4 alkyl, and one of the remaining groups after removing the amino part of various amino acids, and R2 is selected from hydrogen, C1~C4 alkyl, various One of the remaining groups after the amino part is removed from the amino acid, R3 is selected from one of hydrogen and C1-C4 alkyl, and n is any integer from 1 to 4. The benzopyran compound is obtained by extracting, separating and purifying the fermentation broth of Streptomyces xiamenensis CGMCC No.5675. The Xiamenmycin derivatives prepared by the invention have higher performance of inhibiting the proliferation and activity of normal human lung fibroblasts, and can be used to prepare anti-pulmonary fibrosis drugs.

Description

technical field [0001] The invention belongs to the field of natural medicinal chemistry, and in particular relates to a preparation method of a benzopyran compound and an anti-pulmonary fibrosis application. Background technique [0002] At present, there have been some literature reports on benzopyran compounds, namely Xiamenmycin, such as Japanese patents [Kawamura, N. ;Tsuji, E. ;Watanabe, Y. ; Tsuchihashi, K. ; Takako, T. Benzopyran derivatives, their manufacture with Streptomyces species, and their use for treatment of asthma and rheumatoid arthritis. Daiichi Seiyaku Co. , Ltd. ; Mercian Corp. : Kyoto, Japan, 7 March 2000. ] and literature [Xu, M. J. ; Liu, X. J. ; Zhao, Y. L. ; Liu, D. ; Xu, Z. H. ; Lang, X. M. ; Ao, P. ; Lin, W. H. ; Yang, S. L. ; Zhang, Z. G. ;Xu, J. , Identification and characterization of an anti-fibrotic benzopyran compound isolated from mangrove-derived Streptomyces xiamenensis. Mar Drugs 2012, 10, (3), 639-54; Liu, X...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/58A61K31/353A61P11/00C12P17/06C12R1/465
CPCC07D311/58C12P17/06A61P11/00C12N1/205C12R2001/465
Inventor 徐岷涓徐俊张志刚王亚辉
Owner 上海盛通康维药业有限公司
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