Turkish Journal of Chemistry
Article Title
DOI
10.3906/kim-1907-71
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 ± 1.1 μM to 128 ± 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.
Keywords
Tetrahydroquinolines, antitumor activity, Mannich base, green synthesis, multicomponent reaction, heteroaromatics
First Page
1552
Last Page
1569
Recommended Citation
HANASHALSHAHABY, ESAAM HAMIED AHMED; ÜNALEROĞLU, CANAN; CAN, AYŞE AK; ÖZGÜN, ALP; and GARİPCAN, BORA
(2019)
"Design, synthesis, and antitumor evaluation of novel methylene moiety-tethered tetrahydroquinoline derivatives,"
Turkish Journal of Chemistry: Vol. 43:
No.
6, Article 4.
https://doi.org/10.3906/kim-1907-71
Available at:
https://journals.tubitak.gov.tr/chem/vol43/iss6/4
