Thiazoles, thiazolidinones and azetidinones are highly ranked amongst natural and synthetic heterocyclic derivatives due to their great pharmaceutical potential. New thiazolidinone and azetidinone class of bioactive agents based on 4-(2,7-dichloro-9H-fluoren-4-yl)thiazole moiety have been successfully synthesized. 4-(2,7-dichloro-9H-fluoren-4-yl)thiazol-2-amine was synthesized and allowed to react with various aryl/heteroaryl aldehydes to afford the corresponding Schiff base intermediates. The target thiazolidinone and azetidinone analogues have derived from Schiff bases by their reactions with thioglycolic acid and chloroacetyl chloride, respectively. The newly synthesized compounds were then evaluated for their antimicrobial activity against some multidrug resistant strains and examined for cytotoxic activity against normal lung fibroblast (WI-38), human lung carcinoma (A549), and human breast carcinoma (MDA-MB-231) cell lines to develop a novel class of fluorene-based bioactive agents. The mode of action and the binding interaction of the synthesized compound with the active sites of dihydrofolate reductase enzyme were well identified by fluorescence-activated cell sorting (FACS) analysis and molecular docking study. Some of the synthesized compounds showed remarkable activity against A-549 and MDA-MB-231 when compared to Taxol, which was used as a reference drug. 2,7-dichloro-9H-fluorene-based azetidinones are more efficient as antimicrobial and anticancer agents compared to dichloro-9H-fluorene-based thiazolidinones derivatives.

中文翻译：

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生物活性芴。第三部分：2,7-二氯-9H-芴基噻唑烷酮和氮杂环丁酮类似物作为抗癌剂和抗多重耐药菌株的抗菌剂。


噻唑、噻唑烷酮和氮杂环丁酮由于其巨大的药用潜力而在天然和合成杂环衍生物中排名靠前。成功合成了基于4-(2,7-二氯-9H-芴-4-基)噻唑基团的新型噻唑烷酮和氮杂环丁酮类生物活性剂。合成4-(2,7-二氯-9H-芴-4-基)噻唑-2-胺，并使其与各种芳基/杂芳基醛反应，得到相应的席夫碱中间体。目标噻唑烷酮和氮杂环丁酮类似物是通过席夫碱分别与巯基乙酸和氯乙酰氯反应而衍生的。然后评估新合成的化合物对一些多重耐药菌株的抗菌活性，并检查对正常肺成纤维细胞（WI-38）、人肺癌（A549）和人乳腺癌（MDA-MB-231）细胞的细胞毒活性开发一类新型芴基生物活性剂。通过荧光激活细胞分选（FACS）分析和分子对接研究，很好地鉴定了合成化合物的作用模式以及与二氢叶酸还原酶活性位点的结合相互作用。与用作参考药物的紫杉醇相比，一些合成的化合物对 A-549 和 MDA-MB-231 显示出显着的活性。与基于二氯-9H-芴的噻唑烷酮衍生物相比，基于2,7-二氯-9H-芴的氮杂环丁酮作为抗菌剂和抗癌剂更有效。