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Bioactive assessment discovered that 4-chlorobenzyl derivative 11f showed a prominent inhibition on Pseudomonas aeruginosa ATCC 27853 with a low MIC of 1 \u03bcg\/mL, which was four-fold more effective than norfloxacin. Importantly, the highly active 11f with inconspicuous hemolysis towards human red blood cells displayed quite low proneness to trigger bacterial resistance. Preliminary explorations on its antibacterial behavior disclosed that 11f possessed the ability to destroy bacterial cell membrane, leading to increased permeability of inner and outer membranes, the depolarization and fracture of membrane, and the effusion of intracellular components. Furthermore, bacterial oxidative stress and metabolic turbulence aroused by 11f also accelerated bacterial apoptosis. In particular, 11f could not only effectively inset into DNA, but also bind with DNA gyrase through forming supramolecular complex, thereby affecting the biological function of DNA. The above findings of new piperazine hybridized coumarin indolylcyanoenones provided an inspired possibility for the treatment of resistant bacterial infections.<\/jats:p>","DOI":"10.3390\/molecules28062511","type":"journal-article","created":{"date-parts":[[2023,3,10]],"date-time":"2023-03-10T02:05:54Z","timestamp":1678413954000},"page":"2511","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":43,"title":["Synthesis and Biological Evaluation of Piperazine Hybridized Coumarin Indolylcyanoenones with Antibacterial Potential"],"prefix":"10.3390","volume":"28","author":[{"given":"Chunmei","family":"Zeng","sequence":"first","affiliation":[{"name":"Institute of Bioorganic & Medicinal Chemistry, Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Srinivasa Rao","family":"Avula","sequence":"additional","affiliation":[{"name":"Institute of Bioorganic & Medicinal Chemistry, Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7182-4523","authenticated-orcid":false,"given":"Jiangping","family":"Meng","sequence":"additional","affiliation":[{"name":"National & Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, IATTI, College of Pharmacy, Chongqing University of Arts and Sciences, Chongqing 402160, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3233-5465","authenticated-orcid":false,"given":"Chenghe","family":"Zhou","sequence":"additional","affiliation":[{"name":"Institute of Bioorganic & Medicinal Chemistry, Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,3,9]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"7138","DOI":"10.1039\/D2CS00460G","article-title":"Metal organic framework-based antibacterial agents and their underlying mechanisms","volume":"51","author":"Han","year":"2022","journal-title":"Chem. 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