Organotin (IV) complexes from Schiff bases ligands based on 2-amino-3-hydroxypyridine: synthesis, characterization, and
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Medicinal Chemistry Research https://doi.org/10.1007/s00044-020-02630-4
ORIGINAL RESEARCH
Organotin (IV) complexes from Schiff bases ligands based on 2-amino-3-hydroxypyridine: synthesis, characterization, and cytotoxicity José M. Galván-Hidalgo1 Diana M. Roldán-Marchán1 Arturo González-Hernández1 Teresa Ramírez-Apan1 Antonio Nieto-Camacho1 Simón Hernández-Ortega1 Elizabeth Gómez 1 ●
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Received: 2 June 2020 / Accepted: 3 September 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract A multicomponent reaction was used as a synthetic strategy to prepare organotin (IV) complexes, 2-amino-3hydroxypyridine, saliciladehydes 5-R-substituted (H, CH3, OCH3, C(CH)3, F, Cl, Br, I, NO2), and dibutyltin(IV) oxide were used as starting materials. The complexes were analyzed by IR, UV–Visible, MS, NMR of 1H, 13C, 119Sn. The complex 3a was structurally identified by X-ray crystallography, which revealed a dimeric arrangement where the tin atom possess a distorted hexacoordinated environment in which the deprotonated phenolic oxygen atoms and the nitrogen atom of the azomethine from the ligand are coordinated to the metallic center, and one of the phenoxy oxygens bridges with the tin through an intermolecular interaction forming a planar Sn2O2 core. As strategy of molecular design, isosteric and bioisosteric replacement of halogens were employed. All organotin compounds were assessed for their in vitro cytotoxic activity on cancer cell lines K‐562 (chronic myelogenous leukemia), U‐251 (glioblastoma), HCT‐15 (human colorectal cancer), MCF‐7, MDA-MB-231 (human breast cancer), and SKLU‐1 (non‐small‐cell lung cancer). They evidenced an elevated cytotoxic activity, and the inhibitory percentage values stated higher activity than the cis-platin. The K-562 and MDA-MB-231 cells were more sensitive to organotin (IV) complexes than HCT-15 and MCF-7. The organotin (IV) compounds were also tested in vivo for brine shrimp lethality to examine their toxic properties. Keywords Multicomponent reaction Organotin(IV) Schiff base Cytotoxicity Bioisosterism X‐ray crystallography ●
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Introduction Schiff base ligands are some of the most extensively used organic compounds in the biochemistry and chemistry fields. This is owing to their feasibility of synthesis, stability, and their catalytic and pharmacological applications. Additionally, these types of ligands have been employed as biological models to understand the structure of biomolecules and their
Supplementary information The online version of this article (https:// doi.org/10.1007/s00044-020-02630-4) contains supplementary material, which is available to authorized users. * Elizabeth Gómez [email protected] 1
́ Instituto de Quimica, Circuito Exterior s/n, Ciudad Universitaria, Universidad Nacional Autónoma de México (UNAM), 04510 Ciudad de México, México
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bioactivity [1–6]. Schiff bases are simple and highly versatile ligands that also serve as building blocks for various organic substrates of inter
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