{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,1]],"date-time":"2026-07-01T23:04:15Z","timestamp":1782947055182,"version":"3.54.5"},"reference-count":21,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2020,10,7]],"date-time":"2020-10-07T00:00:00Z","timestamp":1602028800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2021,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>In this study, we report the synthesis and antimicrobial activity of some new disubstituted piperazines. Thus, 3\u2010chlorocyclopenta[<jats:italic>c<\/jats:italic>]pyridines and 6\u2010chloropyrano[3,4\u2010<jats:italic>c<\/jats:italic>]pyridine <jats:bold>1<\/jats:bold> under mild reaction conditions with piperazine gave the 3(6)\u2010piperazine\u2010substituted cyclopenta[<jats:italic>c<\/jats:italic>]pyridines and pyrano[3,4\u2010<jats:italic>c<\/jats:italic>]pyridine <jats:bold>2<\/jats:bold>. Furthermore, the latter, by alkylation with 2\u2010chloro\u2010<jats:italic>N<\/jats:italic>\u20101,3\u2010thiazol\u20102\u2010ylacetamide, led to the formation of the target compounds. The evaluation of the antibacterial activity revealed that <jats:bold>3k<\/jats:bold> was the most potent compound. The most sensitive bacterium was found to be <jats:italic>Listeria monocytogenes<\/jats:italic>, whereas <jats:italic>Staphylococcus aureus<\/jats:italic> was the most resistant one. Three compounds, <jats:bold>3d<\/jats:bold>, <jats:bold>3g<\/jats:bold>, and <jats:bold>3k<\/jats:bold>, were tested also against the following resistant strains: methicillin\u2010resistant <jats:italic>S. aureus<\/jats:italic> (MRSA), <jats:italic>Escherichia coli<\/jats:italic>, and <jats:italic>Pseudomonas aeruginosa<\/jats:italic>. All three compounds appeared to be more potent than ampicillin against MRSA. Moreover, compound <jats:bold>3d<\/jats:bold> showed a better activity than the reference drug ampicillin against <jats:italic>P. aeruginosa<\/jats:italic>, whereas <jats:bold>3g<\/jats:bold> was more efficient against <jats:italic>E. coli<\/jats:italic>. The best antifungal activity was observed again for compound <jats:bold>3k<\/jats:bold>. The most resistant fungi appeared to be <jats:italic>Aspergillus fumigatus<\/jats:italic>, whereas <jats:italic>Trichoderma viride<\/jats:italic> seemed the most sensitive one toward the compounds tested. Molecular docking studies on <jats:italic>E. coli<\/jats:italic> MurB, as well as on <jats:italic>Candida albicans<\/jats:italic> CYP51 and dihydrofolate reductase, were used for the prediction of the mechanisms of the antibacterial and antifungal activities, confirming the experimental results.<\/jats:p>","DOI":"10.1002\/ardp.202000208","type":"journal-article","created":{"date-parts":[[2020,10,8]],"date-time":"2020-10-08T06:55:51Z","timestamp":1602140151000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Synthesis and antimicrobial activity of new 2\u2010piperazin\u20101\u2010yl\u2010<i>N<\/i>\u20101,3\u2010thiazol\u20102\u2010ylacetamides of cyclopenta[<i>c<\/i>]pyridines and pyrano[3,4\u2010<i>c<\/i>]pyridines"],"prefix":"10.1002","volume":"354","author":[{"given":"Samvel","family":"Sirakanyan","sequence":"first","affiliation":[{"name":"Scientific Technological Center of Organic and Pharmaceutical Chemistry National Academy of Science of the Republic of Armenia  Yerevan Armenia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Victor","family":"Kartsev","sequence":"additional","affiliation":[{"name":"InterBioscreen  Moscow Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Domenico","family":"Spinelli","sequence":"additional","affiliation":[{"name":"Dipartimento di Chimica G. 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