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Improved preparation method of Rhodomyrtone

A compound and reaction technology, applied in the field of improved preparation of Rhodomyrtone, can solve the problems of low total yield, a large number of explosive and toxic solvents, difficult application, etc., and achieve the effects of cheap solvent, easy synthesis process, and high synthesis yield.

Pending Publication Date: 2022-05-24
JINAN UNIVERSITY
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  • Abstract
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Problems solved by technology

[0017] To sum up, the synthetic route of Rhodomyrtone reported in current literature and patents still has problems such as the need to use silica gel column chromatography for separation, the need to use a large amount of explosive and toxic solvents, and the low overall yield, which is only applicable to tens or hundreds of Milligram-scale preparation, but it is difficult for pilot scale-up or industrial preparation

Method used

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  • Improved preparation method of Rhodomyrtone
  • Improved preparation method of Rhodomyrtone
  • Improved preparation method of Rhodomyrtone

Examples

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Embodiment Construction

[0048] In order to further illustrate the technical effect of the present invention, the present invention will be described in detail below through embodiments. The examples provided are merely illustrative of the methods of the present invention, and are not intended to limit the disclosure of the present invention in any way.

[0049] Unless otherwise specified, the reagents, methods and equipment used in the present invention are conventional reagents, methods and equipment in the art. The compound represented by formula I below is referred to as compound I, the compound represented by formula II is referred to as compound II, and so on.

[0050] In the following examples, compounds II to IV are used as intermediate products, and the purity is greater than 90% after detection, close to 100%, so the amount of the substance is calculated according to the purity of 100%.

[0051] Example Preparation of Rhodomyrtone

[0052] The compound shown in the formula I of the embodim...

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Abstract

The invention discloses an improved Rhodomyrtone preparation method, and relates to the technical field of chemical synthesis, the improved Rhodomyrtone preparation method effectively optimizes each reaction condition and post-treatment mode in the Friedel-Crafts acylation, methylation, reduction reaction, Michael addition and acid-mediated cyclization reaction, and Fries rearrangement reaction processes, and improves the yield of Rhodomyrtone. The problems that silica gel column chromatography separation needs to be used, a large number of explosive and toxic solvents are used, the total yield is low, and the method is only suitable for preparation on the scale of dozens or hundreds of milligrams in an existing synthesis method are solved, the obtained Rhodomyrtone does not need silica gel column chromatography separation, the total yield is high (34.6%), the purity is high (99.8%), and the method is suitable for amplified-scale preparation.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to an improved preparation method of Rhodomyrtone. Background technique [0002] Rhodomyrtone, chemical name: 6,8-dihydroxy-7-(3-methylbutyryl)-9-isobutyl-2,2,4,4-tetramethyl-4,9-dihydro-1H- Xanthene-1,3(2H)-dione is an acylphloroglucinol compound isolated from the traditional Chinese herbal medicine Rhodomyrtustomentosa. According to literature reports, Rhodomyrtone is a new type of natural antibiotic with significant and broad-spectrum antibacterial activity, and its mechanism of action is different from the existing antibiotic drugs that have been marketed. At present, the compound has entered the clinical research stage for the treatment of acne vulgaris (Antibiotics, 2021, 10, 108). Meanwhile, the inventors and others found that Rhodomyrtone can significantly inhibit the diseases caused by herpes simplex virus type I, herpes simplex virus type II, varicella-zoster ...

Claims

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Application Information

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IPC IPC(8): C07D311/86
CPCC07D311/86
Inventor 叶文才胡利军王英段之章
Owner JINAN UNIVERSITY
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