Abstract
Novel methylene-tethered tetrahydroquinolines (THQs) and cyclopenta[$b$]pyridines were synthesized by one-pot multicomponent reactions of Mannich bases, enolizable ketones, and NH$_{4}$OAc in water by an environmentally friendly K-10 montmorillonite clay-catalyzed reaction. The cytotoxic activities of 1-(2-methyl-8-methylene-5,6,7,8-tetrahydroquinolin-3-yl)ethanone (9a), ethyl 2-methyl-8-methylene-5,6,7,8-tetrahydroquinoline-3 carboxylate (9b), and 1-(2-methyl-7-methylene-6,7-dihydro-5$H$-cyclopenta[$b$]pyridin-3-yl)ethanone (11a) were tested against rat glioblastoma (C6), human breast cancer (MCF-7), prostate cancer (PC3), neuroblastoma (SH-SY5Y), and mouse fibroblast (L929) cell lines in a concentration-dependent (50-300 μM) and time-dependent (24-72 h) manner and expressed as IC$_{50\, }$values. The results showed that compound 9a induced the lowest IC$_{50\, }$values in all cell lines ranging from 111 p 1.1 μM to 128 p 1.3 μM when compared to 9b and 11a after 72 h. As an evaluation of antibacterial properties, a swarming motility assay was performed with the Pseudomonas aeruginosa PA01 strain and compound 9a showed higher inhibition of swarming motility.
Highlights
Cancer is the second main cause of death worldwide [1]
As part of our ongoing work on quinoline chemistry, we report a new approach for the synthesis of new methylene-tethered THQs and cyclopenta[b]pyridines to explore their cytotoxic effects on rat glioblastoma (C6), human breast cancer (MCF-7), prostate cancer (PC3), neuroblastoma (SH-SY5Y), and mouse fibroblast (L929) cell lines
Key components 2,6-dimethylenecyclohexanone and 2,5-dimethylenecyclopentanone were obtained in situ from Mannich bases 7 and 10, which were prepared from commercially available starting materials according to the methods reported in the literature [30]
Summary
Cancer is the second main cause of death worldwide [1]. A large number of studies have been devoted to exploring new biologically active compounds as antitumor therapeutic agents to be used in chemotherapeutic drug systems [2,3]. As part of our ongoing work on quinoline chemistry, we report a new approach for the synthesis of new methylene-tethered THQs and cyclopenta[b]pyridines to explore their cytotoxic effects on rat glioblastoma (C6), human breast cancer (MCF-7), prostate cancer (PC3), neuroblastoma (SH-SY5Y), and mouse fibroblast (L929) cell lines. At a higher dose (300 μM), C6 cells showed a rapid cytotoxic response to compound 9b when compared to other cell lines.
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