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Refluxing of arylidene <jats:bold>3<\/jats:bold> with \u03b1-ketohydrazonoyl halides <jats:bold>4\u20137<\/jats:bold> in the presence of triethylamine in chloroform afforded dihydropyrrolo[2,1-<jats:italic>a<\/jats:italic>]isoquinolines <jats:bold>11\u201314<\/jats:bold>. Claisen\u2013Schmidt condensation of <jats:bold>11<\/jats:bold> with aryl aldehydes <jats:bold>15a-f<\/jats:bold> or pyrazole aldehydes <jats:bold>17a-d<\/jats:bold> in ethanol in the presence of sodium hydroxide solution produced chalcones <jats:bold>16a-f<\/jats:bold> and <jats:bold>18a-d<\/jats:bold>. Refluxing of chalcone <jats:bold>16f<\/jats:bold> with hydrazine hydrate in ethanol afforded pyrazoline <jats:bold>19<\/jats:bold> which gave <jats:italic>N<\/jats:italic>-phenylcarbothioamide derivative <jats:bold>20<\/jats:bold> on stirring with phenyl isothiocyanate in dry ether. Also, refluxing of <jats:bold>19<\/jats:bold> with acetic anhydride or formic acid afforded acetyl-pyrazoline derivative <jats:bold>21<\/jats:bold> or formyl-pyrazoline derivative <jats:bold>22<\/jats:bold>, respectively. Antitumor activity for some new synthesized compounds showed that compounds <jats:bold>16b<\/jats:bold> and <jats:bold>16d<\/jats:bold> had anticancer activities. Antimicrobial activities for the newly synthesized compounds revealed the most potent compounds <jats:bold>16c<\/jats:bold>, <jats:bold>18b<\/jats:bold> and <jats:bold>18d<\/jats:bold> against <jats:italic>E. coli<\/jats:italic>, compounds <jats:bold>16b<\/jats:bold>, <jats:bold>18b<\/jats:bold> and <jats:bold>18d<\/jats:bold> against <jats:italic>B. mycoides<\/jats:italic>, and compounds <jats:bold>16b<\/jats:bold>, <jats:bold>16c<\/jats:bold> and <jats:bold>18b<\/jats:bold> against <jats:italic>C. albicans<\/jats:italic>. Moreover, compound <jats:bold>18b<\/jats:bold> had the lowest MIC values against <jats:italic>E. coli<\/jats:italic> and <jats:italic>B. mycoides<\/jats:italic>, with MIC values of 40 and 60\u00a0\u00b5g\/ml, respectively.<\/jats:p>","DOI":"10.1186\/s13065-025-01557-4","type":"journal-article","created":{"date-parts":[[2025,7,8]],"date-time":"2025-07-08T07:40:58Z","timestamp":1751960458000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Synthesis, reactions, antitumor and antimicrobial activity of new 5,6-dihydropyrrolo[2,1-a]isoquinoline chalcones"],"prefix":"10.1186","volume":"19","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5513-3941","authenticated-orcid":false,"given":"Mohamed A. 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