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Synthesis, Spectroscopic Characterization, Structural Studies, and In Vitro Antitumor Activities of Pyridine-3-carbaldehyde Thiosemicarbazone Derivatives
Joint Authors
Manzur, Jorge
Hernández, Wilfredo
Spodine, Evgenia
Carrasco, Fernando
Icker, Maik
Krautscheid, Harald
Beyer, Lothar
Vaisberg, Abraham
Source
Issue
Vol. 2020, Issue 2020 (31 Dec. 2020), pp.1-12, 12 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2020-09-14
Country of Publication
Egypt
No. of Pages
12
Main Subjects
Abstract EN
Eight new thiosemicarbazone derivatives, 6-(1-trifluoroethoxy)pyridine-3-carbaldehyde thiosemicarbazone (1), 6-(4′-fluorophenyl)pyridine-3-carbaldehyde thiosemicarbazone (2), 5-chloro-pyridine-3-carbaldehyde thiosemicarbazone (3), 2-chloro-5-bromo-pyridine-3-carbaldehyde thiosemicarbazone (4), 6-(3′,4′-dimethoxyphenyl)pyridine-3-carbaldehyde thiosemicarbazone (5), 2-chloro-5-fluor-pyridine-3-carbaldehyde thiosemicarbazone, (6), 5-iodo-pyridine-3-carbaldehyde thiosemicarbazone (7), and 6-(3′,5′-dichlorophenyl)pyridine-3-carbaldehyde thiosemicarbazone (8) were synthesized, from the reaction of the corresponding pyridine-3-carbaldehyde with thiosemicarbazide.
The synthesized compounds were characterized by ESI-Mass, UV-Vis, IR, and NMR (1H, 13C, 19F) spectroscopic techniques.
Molar mass values and spectroscopic data are consistent with the proposed structural formulas.
The molecular structure of 7 has been also confirmed by single crystal X-ray diffraction.
In the solid state 7 exists in the E conformation about the N2-N3 bond; 7 also presents the E conformation in solution, as evidenced by 1H NMR spectroscopy.
The in vitro antitumor activity of the synthesized compounds was studied on six human tumor cell lines: H460 (lung large cell carcinoma), HuTu80 (duodenum adenocarcinoma), DU145 (prostate carcinoma), MCF-7 (breast adenocarcinoma), M-14 (amelanotic melanoma), and HT-29 (colon adenocarcinoma).
Furthermore, toxicity studies in 3T3 normal cells were carried out for the prepared compounds.
The results were expressed as IC50 and the selectivity index (SI) was calculated.
Biological studies revealed that 1 (IC50 = 3.36 to 21.35 μM) displayed the highest antiproliferative activity, as compared to the other tested thiosemicarbazones (IC50 = 40.00 to >582.26 μM) against different types of human tumor cell lines.
1 was found to be about twice as cytotoxic (SI = 1.82) than 5-fluorouracile (5-FU) against the M14 cell line, indicating its efficiency in inhibiting the cell growth even at low concentrations.
A slightly less efficient activity was shown by 1 towards the HuTu80 and MCF7 tumor cell lines, as compared to that of 5-FU.
Therefore, 1 can be considered as a promising candidate to be used as a pharmacological agent, since it presents significant activity and was found to be more innocuous than the 5-FU anticancer drug against the 3T3 mouse embryo fibroblast cells.
American Psychological Association (APA)
Hernández, Wilfredo& Carrasco, Fernando& Vaisberg, Abraham& Spodine, Evgenia& Manzur, Jorge& Icker, Maik…[et al.]. 2020. Synthesis, Spectroscopic Characterization, Structural Studies, and In Vitro Antitumor Activities of Pyridine-3-carbaldehyde Thiosemicarbazone Derivatives. Journal of Chemistry،Vol. 2020, no. 2020, pp.1-12.
https://search.emarefa.net/detail/BIM-1181550
Modern Language Association (MLA)
Hernández, Wilfredo…[et al.]. Synthesis, Spectroscopic Characterization, Structural Studies, and In Vitro Antitumor Activities of Pyridine-3-carbaldehyde Thiosemicarbazone Derivatives. Journal of Chemistry No. 2020 (2020), pp.1-12.
https://search.emarefa.net/detail/BIM-1181550
American Medical Association (AMA)
Hernández, Wilfredo& Carrasco, Fernando& Vaisberg, Abraham& Spodine, Evgenia& Manzur, Jorge& Icker, Maik…[et al.]. Synthesis, Spectroscopic Characterization, Structural Studies, and In Vitro Antitumor Activities of Pyridine-3-carbaldehyde Thiosemicarbazone Derivatives. Journal of Chemistry. 2020. Vol. 2020, no. 2020, pp.1-12.
https://search.emarefa.net/detail/BIM-1181550
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-1181550