{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T13:12:29Z","timestamp":1788441149542,"version":"build-2803163510"},"reference-count":19,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2012,10,4]],"date-time":"2012-10-04T00:00:00Z","timestamp":1349308800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0"}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["DARU J Pharm Sci"],"published-print":{"date-parts":[[2012,12]]},"abstract":"<jats:title>Abstract<\/jats:title>\n          <jats:sec>\n            <jats:title>Background<\/jats:title>\n            <jats:p>The currently available antifungal drugs suffer from toxicity, greatest potential drug interactions with other drugs, insufficient pharmacokinetics properties, and development of resistance. Thus, development of new antifungal agents with optimum pharmacokinetics and less toxicity is urgent task. In the search for new azole antifungals, we have been previously described azolylchromanone oxime ethers as rigid analogs of oxiconazole. In continuation of our work, we incorporated phenylhydrazone moiety instead of oxime ether fragment in azolylchromanone derivatives.<\/jats:p>\n          <\/jats:sec>\n          <jats:sec>\n            <jats:title>Methods<\/jats:title>\n            <jats:p>The 3-azolyl-4-chromanone phenylhydrazones were synthesized via ring closure of 2-azolyl-2'-hydroxyacetophenones and subsequent reaction with phenylhydrazine. The biological activity of title compounds was evaluated against different pathogenic fungi including <jats:italic>Candida albicans<\/jats:italic>, <jats:italic>Saccharomyces cerevisiae<\/jats:italic>, <jats:italic>Aspergillus niger<\/jats:italic>, and <jats:italic>Microsporum gypseum<\/jats:italic>. Docking study, <jats:italic>in silico<\/jats:italic> toxicity risks and drug-likeness predictions were used to better define of title compounds as antifungal agents.<\/jats:p>\n          <\/jats:sec>\n          <jats:sec>\n            <jats:title>Results<\/jats:title>\n            <jats:p>The <jats:italic>in vitro<\/jats:italic> antifungal activity of compounds based on MIC values revealed that all compounds showed good antifungal activity against <jats:italic>C. albicans<\/jats:italic>, <jats:italic>S. cerevisiae<\/jats:italic> and <jats:italic>M. gypseum<\/jats:italic> at concentrations less than 16 \u03bcg\/mL. Among the test compounds, 2-methyl-3-imidazolyl derivative <jats:bold>3b<\/jats:bold> showed the highest values of drug-likeness and drug-score.<\/jats:p>\n          <\/jats:sec>\n          <jats:sec>\n            <jats:title>Conclusion<\/jats:title>\n            <jats:p>The 3-azolyl-4-chromanone phenylhydrazones considered as analogs of 3-azolyl-4-chromanone oxime ethers basically designed as antifungal agents. The antifungal activity of title compounds was comparable to that of standard drug fluconazole. The drug-likeness data of synthesized compounds make them promising leads for future development of antifungal agents.<\/jats:p>\n          <\/jats:sec>","DOI":"10.1186\/2008-2231-20-46","type":"journal-article","created":{"date-parts":[[2012,10,4]],"date-time":"2012-10-04T14:14:40Z","timestamp":1349360080000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":43,"title":["Synthesis, in vitro antifungal evaluation and in silico study of 3-azolyl-4-chromanone phenylhydrazones"],"prefix":"10.1186","volume":"20","author":[{"given":"Adile","family":"Ayati","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mehraban","family":"Falahati","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hamid","family":"Irannejad","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Saeed","family":"Emami","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2012,10,4]]},"reference":[{"key":"60_CR1","doi-asserted-by":"publisher","first-page":"S1","DOI":"10.1097\/01.qco.0000399602.83515.ac","volume":"24","author":"PG Pappas","year":"2011","unstructured":"Pappas PG: The role of azoles in the treatment of invasive mycoses: review of the Infectious Diseases Society of America guidelines. 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