A pleuromutilin derivative containing a 2-thio-4-thiazolidinone side chain, and its preparation method and application

By introducing a 2-thio-4-thiazolidinone structure into the C-14 side chain of pleuromutilin, a new pleuromutilin derivative was synthesized, which solved the problems of cross-resistance of antibacterial drugs and insufficient inhibition of Gram-positive bacteria in the existing technology, and achieved effective inhibition of Staphylococcus aureus and Streptococcus, especially antibacterial activity against MRSA.

CN118894818BActive Publication Date: 2025-09-09LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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Patent Information

Application Number
CN202410952695.7
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2024-07-16
Publication Date
2025-09-09
Estimated Expiration
2044-07-16

AI Technical Summary

Technical Problem

Existing pleuromutilin compounds have cross-resistance problems among antibacterial drugs and lack effective inhibitory activity against Gram-positive bacteria such as Staphylococcus aureus and Streptococcus.

Method used

A new pleuromutilin derivative is synthesized by introducing a 2-thio-4-thiazolidinone structure into the C-14 side chain of pleuromutilin. A compound with good antibacterial activity is obtained through specific synthetic steps including the preparation of intermediates and reaction optimization.

Benefits of technology

The synthesized truncated pleuromutilin derivatives containing 2-thio-4-thiazolidinone side chains show significant antibacterial activity against Gram-positive bacteria such as Staphylococcus aureus and Streptococcus, and are especially effective against drug-resistant bacteria MRSA, and have good application prospects.

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Abstract

The present invention discloses a pleuromutilin derivative containing a 2-thio-4-thiazolidinone side chain, and its preparation method and application. The preparation method is as follows: first, pleuromutilin and p-toluenesulfonyl chloride are added to methyl tert-butyl ether, sodium hydroxide solution is added dropwise with stirring, and the reaction is refluxed to obtain intermediate 1; then, 2-thio-4-thiazolidinone is added to acetonitrile, anhydrous potassium carbonate is added and stirred at room temperature for 20 minutes, and then intermediate 1 is added, and the reaction is stirred at room temperature for a certain time to obtain intermediate 2; finally, intermediate 2 and an acyl chloride with different group donors are added to dichloromethane, and under the catalysis of triethylamine, stirred at room temperature for a certain time to obtain a pleuromutilin derivative containing a 2-thio-4-thiazolidinone side chain. The present invention synthesizes a pleuromutilin derivative containing a 2-thio-4-thiazolidinone side chain with good antibacterial activity through a simple preparation process, with high yield, good antibacterial activity against drug-resistant bacteria, and good application prospects.
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