Synthesis and Antitumoral Evaluation of 7-chloro-4-quinolinylhydrazones Derivatives

Abstract

A series of twenty-one 7-chloro-4-quinolinylhydrazones derivatives (3a-u) have been synthesized and evaluated for their cytotoxic potential against three cancer cell lines using MTT assay. The compounds 3b, 3e, 3f, 3h, 3j, 3n, 3r and 3u displayed more than 90% of growth inhibition (GI) and they were selected for in vitro anticancer activities evaluation against four human cancer cell lines. These results were expressed as the concentrations that induce 50% inhibition of cell growth (IC50) in μg/mL. Considering that, compounds 3b, 3e, 3h, 3n, 3r and 3u exhibited good cytotoxic activity against at least three cancer cell lines (0.7967-4.200 μg/mL). In general, we observed that the presence of electron-withdrawing groups in the benzene ring is important for the anticancer activity in this series, such as fluorine (3h), chlorine (3b) amd bromine (3e) groups in meta position and nitro group (3r) in para position. These derivatives could be considered interesting start points to develop a new anticancer drug and confirm the potential of chloroquine derivatives as lead compounds in anticancer drug discovery.

7-Chloroquinolinehydrazones as First-in-Class Anticancer Experimental Drugs in the NCI-60 Screen among Different Investigated Series of Aryl, Quinoline, Pyridine, Benzothiazole and Imidazolehydrazones

“…7-Chloroquinoline hydrazones have been previously developed and successfully tested in vitro for many biological activities [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 ]. The major part of the studies has been carried out to identify their antimalarial properties [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 ].…”

“…The major part of the studies has been carried out to identify their antimalarial properties [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 ]. In addition, these hydrazones were explored for their anti-leishmanial [ 10 , 11 , 12 , 13 ], anti-tubercular [ 3 , 14 , 15 , 16 , 17 , 18 ], anti-bacterial [ 19 , 20 ], anti-oxidant [ 21 , 22 ], anti-fungal [ 23 , 24 ], anti-viral [ 25 ], anti-inflammatory [ 26 ], anti-prion disease [ 27 ], anti-convulsant [ 28 ], antinociceptive [ 29 ], but also anticancer activities [ 30 , 31 , 32 , 33 ]. Many chemical modulations have been realized on 7-chloroquinoline hydrazones.…”

Synthesis and Characterization of Chemical Compounds Derived From Benzohydrazide and Evaluation of Their Antibacterial Activities

“…methanol for antioxidant and cytotoxic properties (14), 2-chloro-3-(l, 3-dioxolan-2-yl) quinolines for DPPH free radical scavenging activities (15), 2-chloro quinoline-3-carbaldehyde derived Schiff bases for antimicrobial activities (16), 7-chloro-4-quinolinylhydrazone derivatives for antitumoral properties (17), N-(2-(arylmethylimino) ethyl)-7-chloroquinolin-4-amine derivatives for fighting with Zika virus function (18), 1-(7-Chloroquinolin-4-yl)-2-[(1H-pyrrol-2-yl) methylene] hydrazine as an anticancer agent (19), 4-[(p-Aminobenzenesulfonamide-N 1 -(2′pyridinil)]-7-chloroquinoline derivatives as promising antimalarial compounds (20), and finally natural and synthetic chloroquinolone derivatives for in vivo and in vitro antioxidant features (21). Some review articles have also inspected the chemical reactions, synthetic methods, and biological properties of 2-chloroquinoline-3-carbaldehyde in the articles published between the years 1979-2017 (22)(23)(24).…”