Synthesis, Characterization, and Antibacterial Activities of Organotin(IV) Complexes with 2‐Acetylpyridine‐N(4)‐cyclohexylthiosemicarbazone (HAPCT)

Abstract

The reaction of 2‐acetylpyridine‐N(4)‐cyclohexylthiosemicarbazone [(HAPCT), (1)] ligand with organotin(IV) chloride(s) afforded the five new organotin(IV) complexes: [MeSnCl2(APCT)] (2), [BuSnCl2(APCT)] (3), [PhSnCl2(APCT)] (4), [Me2SnCl(APCT)] (5), and [Ph2SnCl(APCT)] (6). The ligand (1) and its organotin(IV) complexes (2–6) have been synthesized and characterized by CHN analyses, molar conductivity, UV–vis, FT IR, 1H, 13C, and 119Sn NMR spectral studies. The single crystal X‐ray diffraction studies indicated that [PhSnCl2(APCT)] (4) is six coordinated and strongly adopts a distorted octahedral configuration with the coordination through pyridine‐N, azomethine‐N, and thiolato‐S atoms of the ligand. The compound crystallizes into a monoclinic lattice with the space group P21/n. The ligand (1) and its organotin(IV) complexes (2–6) were assayed for in vitro antibacterial activity against Staphylococcus aureus, Escherichia coli, Enterobacter aerogenes, and Salmonella typhi. The screening results have shown that the organotin(IV) complexes (2–6) have better antibacterial activity than the free ligand. Furthermore, it has been shown that the diphenyltin(IV) derivative (6) exhibits significantly better activities than the other organotin(IV) derivatives (2–5). © 2012 Wiley Periodicals, Inc. Heteroatom Chem 24:43–52, 2013; View this article online at http://wileyonlinelibrary.com. DOI 10.1002/hc.21061

Synthesis, crystal structures and spectroscopic properties of two new organotin (IV) complexes and their antiproliferative effect against cancerous and non-cancerous cells

“…Discovery of cis-platin by Rosenberg [55] and its new marketing analogues (carboplatin, lobaplatin, oxaliplatin, nedaplatin) have further created interest in metal-based anticancer drugs [1,56]. Tin complexes have been studied in detail as antibacterial agents [9,15,[17][18][19]28] and recently against cancerous cell lines [12,26,57] other than colon cancer. In the current study, complexes 1-2 were tested against three cancerous cell lines (human colon cancer HCT 116, breast cancer MCF-7, leukemia K562) and a non-cancerous cell line (3T3-L1).…”

“…Tin is a non-transition and biocompatible metal [5][6][7] and its complexes have shown significant antibacterial properties [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22]. However, tin complexes have been rarely studied against cancer [12,[23][24][25][26][27][28].…”

Schiff base‐nickel, palladium, and platinum complexes derived from N‐cyclohexyl hydrazine carbothioamide and 3‐hydroxy‐4‐methoxybenzaldehyde: Selective antiproliferative and proapoptotic effects against colorectal carcinoma

“…Thiosemicarbazones having ONS coordinating sites are important in coordination chemistry due to their strong bonding ability with transition metals (Alomar, Khan, Allain, & Bouet, ; Rayati, Sadeghzadeh, & Khavasi, ; Siddiki et al, ; Vieites et al, ). Researchers have focused on Pt(II) and Pd(II) complexes containing N and S donors due to metal based drugs exhibiting significant anticancer activity with lower toxicity and adverse effects (Faraglia et al, ; Salam, Affan, Arafat, Saha, & Nasrin, ).…”

“…Pd(II) complexes containing N and S donors due to metal based drugs exhibiting significant anticancer activity with lower toxicity and adverse effects (Faraglia et al, 2001;Salam, Affan, Arafat, Saha, & Nasrin, 2013).…”

The structure–activity relationship of some hexacoordinated dimethyltin(IV) complexes of fluorinated β‐diketone/β‐diketones and sterically congested heterocyclic β‐diketones

“…Some organotin(IV) complexes are potentially active biological agents and have great impact in the biosphere. Organotin(IV) complexes are used as fungicides, bactericides, antioxidants, analgesics and insecticides . Diorganotin(IV) complexes attract considerable interest in biological applications owing to their use as antineoplastic agents .…”