AI Article Synopsis
- A new method for synthesizing aurachin D, a type of quinolone alkaloid that targets cytochrome oxidase, was developed using an oxazoline ring-opening reaction to create various electron-poor and electron-rich analogues.!* -
- The synthesized aryl-substituted and side-chain-modified aurachin D analogues were tested for their ability to inhibit cytochrome oxidase and bacterial growth, showing significant inhibition with certain compounds.!* -
- While the aurachin D and its analogues did not affect nonpathogenic bacteria, the citronellyl and 6-fluoro-substituted analogues demonstrated moderate growth inhibition against pathogenic bacteria, with MIC values between 4-8
Article Abstract
A revised total synthesis of aurachin D (), an isoprenoid quinolone alkaloid that targets () cytochrome (cyt-) oxidase, was accomplished using an oxazoline ring-opening reaction. The ring opening enabled access to a range of electron-poor analogues, while electron-rich analogues could be prepared using the Conrad-Limpach reaction. The aryl-substituted and side-chain-modified aurachin D analogues were screened for inhibition of cyt- oxidase and growth inhibition of . Nanomolar inhibition of cyt- oxidase was observed for the shorter-chain analogue (citronellyl side chain) and the aryl-substituted analogues / (fluoro substituent at C6/C7), / (hydroxy substituent at C5/C6) and // (methoxy substituent at C5/C6/C7). Aurachin D and the analogues did not inhibit growth of nonpathogenic , but the citronellyl () and 6-fluoro-substituted () inhibitors from the cyt- oxidase assay displayed moderate growth inhibition against pathogenic (MIC = 4-8 μM).
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9575164 | PMC |
| http://dx.doi.org/10.1021/acsmedchemlett.2c00401 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!