Organotin Compound Derived from 3‐Hydroxy‐2‐formylpyridine Semicarbazone: Synthesis, Crystal Structure, and Antiproliferative Activity

Abstract

The novel diphenyltin(IV) compound [Ph2(HyFoSc)Sn] (2), where H2HyFoSc (1) is 3-hydroxy-2-formylpyridine semicarbazone, was prepared and characterized by vibrational and NMR (1H, 13C) spectroscopy. The structure of [Ph2(HyFoSc)Sn] was confirmed by single-crystal X-ray crystallography. The doubly deprotonated ligand is coordinated to the tin atom through the enolic-oxygen, the azomethine-nitrogen, and phenolic-oxygen, and so acts as an anionic tridentate ligand with the ONO donors. Two carbon atoms complete the fivefold coordination at the tin(IV) center. Intermolecular hydrogen bonding, C–H → π, and π → π interactions combine to stabilize the crystal structure. Compounds 1 and 2 have been evaluated for antiproliferative activity in vitro against the cells of three human tumor cell lines: MCF-7 (human breast cancer cell line), T24 (bladder cancer cell line), A549 (nonsmall cell lung carcinoma), and a mouse fibroblast L-929 cancer cell line.

Synthesis, Characterization and DNA Binding Studies of (E)-1-((Pyridin-2-yl)methylidene) semicarbazide Mn(II), Co(II), Ni(II) and Cu(II) Complexes

“…The signals at δ = 9.32 (1H, s) and δ = 8.15 (1H, s) can be assigned to -NH-and =CH-respectively. The multiplet at δ = 8.06 to 7.46 (m, 4H) is due to absorptions of aromatic ring hydrogen atoms (-ArH) [45]. Similar spectra of 2 shows -NH 2 at δ = 12.34 and 11.44 (2H), -NH-at δ = 10.12 (1H), =CH-at δ = 9.05 (1H) and absorption of aromatic H atoms (ArH) at δ = 8.64 to 7.77 (m, 4H) (Fig.…”

De novo unified robust antidiabetic pharmacophores based on biopotent hybrid material: DFT‐assisted design, optimized molecular structure, and understanding mechanism of antidiabetic bioassay

“…Diorganotin(IV) complexes of semicarbazones and other ligands 29 have been reported to possess different bioactivities. 30 Therefore, it was thought worthwhile to synthesize some new dimethyltin(IV) complexes of semicarbazones derived from heterocyclic β-diketones. These complexes were characterized by spectroscopic techniques and by mass spectrometry.…”

The Effectiveness of Organotin (IV) Benzylisopropyldithiocarbamate Compounds as Insecticide Against <i>Aedes Aegypti</i> Linn (Diptera: Culicidae) in Laboratory

“…Wide application of organotin (IV) compounds in the industry (Boraiko and Batt, 2005) and its potential in biological activity has attracted researchers to conduct studies on this compound (Wiecek et al, 2010). Among the biological activities of organotin (IV) compound have these compounds identified as a potential antiviral agent (Sreeja and Kurup, 2005), antineoplastic agents, antituberculosis (Gielen, 2002;Dokorou et al, 2004;Kovala-Demertzi et al, 2005;Kovala-Demertzi, 2006), antibacterial agent (Jamil et al, 2009), anticancer agent (Awang et al, 2010) and so on.…”