Design, synthesis, and antitumor evaluation of novel methylene moiety-tethered tetrahydroquinoline derivatives

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Hanashalshahaby E. H. A., ÜNALEROĞLU C., Can A. A. K., Ozgun A., GARİPCAN B.

TURKISH JOURNAL OF CHEMISTRY, vol.43, no.6, pp.1552-1569, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 43 Issue: 6
  • Publication Date: 2019
  • Doi Number: 10.3906/kim-1907-71
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.1552-1569
  • Keywords: Tetrahydroquinolines, antitumor activity, Mannich base, green synthesis, multicomponent reaction, heteroaromatics, 1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES, ANTIINFLAMMATORY ACTIVITY, ANTICANCER EVALUATION, POTENT, 5,6,7,8-TETRAHYDROQUINOLINES, CYTOTOXICITY, INHIBITORS
  • Hacettepe University Affiliated: Yes


Novel methylene-tethered tetrahydroquinolines (THQs) and cyclopenta[b]pyridines were synthesized by one-pot multicomponent reactions of Mannich bases, enolizable ketones, and NH4 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 mu M) and time-dependent (24-72 h) manner and expressed as IC50 values. The results showed that compound 9a induced the lowest IC50 values in all cell lines ranging from 111 +/- 1.1 mu M to 128 +/- 1.3 mu M 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.