Synthesis, structural characterization and cytotoxic activity of organotin derivatives of indomethacin

Camacho‐Camacho, Carlos; Rojas-Oviedo, Irma; Paz-Sandoval, M. Ángeles; Cárdenas, Jorge; Toscano, Rubén A.; Gielen, Marcel; Sosa, Lidia Barrón; Bártez, Francisco Sánchez; Gracia-Mora, Isabel

doi:10.1002/aoc.1366

Cited by 22 publications

(29 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The design of organotin derivatives with biologically important ligands, like antibiotics [7, 8], anticancer drugs, [9] and some other biologically relevant substrates [10], has been explored in the past years [11]. Organotin derivatives of amino acids have been of interest as possible biocides [12]; for example, tricyclohexyltin alaninate is a powerful fungicide and bactericide [13].…”

Section: Introductionmentioning

confidence: 99%

Novel Organotin(IV) Schiff Base Complexes with Histidine Derivatives: Synthesis, Characterization, and Biological Activity

Garza-Ortiz

Camacho‐Camacho

Sainz‐Espuñes

et al. 2013

Bioinorganic Chemistry and Applications

Self Cite

View full text Add to dashboard Cite

Five novel tin Schiff base complexes with histidine analogues (derived from the condensation reaction between L-histidine and 3,5-di-tert-butyl-2-hydroxybenzaldehyde) have been synthesized and characterized. Characterization has been completed by IR and high-resolution mass spectroscopy, 1D and 2D solution NMR (1H, 13C and 119Sn), as well as solid state 119Sn NMR. The spectroscopic evidence shows two types of structures: a trigonal bipyramidal stereochemistry with the tin atom coordinated to five donating atoms (two oxygen atoms, one nitrogen atom, and two carbon atoms belonging to the alkyl moieties), where one molecule of ligand is coordinated in a three dentate fashion. The second structure is spectroscopically described as a tetrahedral tin complex with four donating atoms (one oxygen atom coordinated to the metal and three carbon atoms belonging to the alkyl or aryl substituents), with one molecule of ligand attached. The antimicrobial activity of the tin compounds has been tested against the growth of bacteria in vitro to assess their bactericidal properties. While pentacoordinated compounds 1, 2, and 3 are described as moderate effective to noneffective drugs against both Gram-positive and Gram-negative bacteria, tetracoordinated tin(IV) compounds 4 and 5 are considered as moderate effective and most effective compounds, respectively, against the methicillin-resistant Staphylococcus aureus strains (Gram-positive).

show abstract

Section: Introductionmentioning

confidence: 99%

Novel Organotin(IV) Schiff Base Complexes with Histidine Derivatives: Synthesis, Characterization, and Biological Activity

Garza-Ortiz

Camacho‐Camacho

Sainz‐Espuñes

et al. 2013

Bioinorganic Chemistry and Applications

Self Cite

View full text Add to dashboard Cite

show abstract

“…Organotin compounds have been studied as possible candidates for anticancer compounds, fungicides or bactericides, and they have been studied for the treatment of leishmaniasis. [1][2][3][4][5][6][7][8] It is recognized that the synthesis of metal coordinated compounds of ligands with well-known biological activity could result in important biological activity. In this way, a designed metal-based compound combines ligands with important biological activity and pharmacologically active metal in a single chemical moiety.…”

Section: Introductionmentioning

confidence: 99%

“…[10] The difference between asymmetric and symmetric O&bond; C=O stretching vibrations (Δν) has been used to determine the mode of coordination of a carboxylate ligand with metals. [1,17,18] Differences larger than 250 cm H NMR spectra of the complexes show that the signal assigned to azomethine proton N=CH (H-11, Fig. 1) appears in the range 8.04-8.43 ppm (Table 1) for all compounds.…”

mentioning

confidence: 97%

Tributyltin(IV) Schiff base complexes with amino acid derivatives: synthesis, characterization and biological activity

Camacho‐Camacho

Rojas-Oviedo

Garza-Ortiz

et al. 2016

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

The synthesis in one-pot reactions and structural characterization of six new tri-n-butyltin(IV) derivatives of Schiff bases are reported. The compounds are derived from a condensation reaction between L-alanine, L-valine, L-isoleucine, L-methionine, L-phenylalanine or L-tryptophan and 3,5-di-tert-butyl-2-hydroxybenzaldehyde. Characterization was completed using elemental analysis, infrared spectroscopy, mass spectrometry, one-and two-dimensional solution NMR ( Sn NMR. In addition, the crystal structures of three of the compounds were confirmed using single-crystal X-ray diffraction. Although five-coordinated and polymeric in the solid state, the tin compounds are four-coordinated and monomeric in solution. The coordination environment around the triorganotin units comprises three carbon atoms and two oxygen atoms from two ligands in a trigonal bipyramidal geometry. The anti-proliferative effect of these compounds on the cervical carcinoma cell lines HeLa, CaSki and ViBo was screened in vitro, the compounds showing cytotoxic activity against all three strains and null or low cytotoxic activity (necrotic) as well.

show abstract

“…1). Furthermore, Camaco-Camaco et al [6] have reported the synthesis and in vitro cytotoxicity of various indomethacinderived n-alkyl-tin complexes, while Jones et al [7] reported the cytotoxic activity of a new indomethacin Scheme 1. Synthesis of benzimidazoles 8 -10, imidazolo-pyridine 11, purine 12, and benzothiazole 13 derivatives from indomethacin (1) and various arene diamines (2 -6) and 2-aminobenzenethiol (7).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and anti-HIV Activity of New Benzimidazole, Benzothiazole and Carbohyrazide Derivatives of the anti-Inflammatory Drug Indomethacin

Al‐Masoudi

Jafar²,

Baqir³

et al. 2011

Zeitschrift Für Naturforschung B

View full text Add to dashboard Cite

There is an urgent need for the design and development of new and safer drugs for the treatment of HIV infection, active against the currently resistant viral strains. New derivatives of the non-steroidal anti-inflammatory drug indomethacin bearing benzimidazoles, benzothiazole, purine and pyridine residues 8 -13 were synthesized with the aim of developing new non-nucleoside reverse transcriptase inhibitors (NNRTIs). Alternatively, new imine analogs 16 -20 were synthesized from condensation of indomethacinyl hydrazide 15, prepared from the ester 14, with various ketone precursors. Treatment of 15 with phenyl isothiocyanate or triethyl orthoformate afforded the phenylcarbonothioyl and the oxadiazole derivatives 21 and 22, respectively. The new compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. Compounds 9 and 10 were the most active in inhibiting HIV-2 and HIV-1, respectively, with EC 50 ≥ 17.60 µg mL −1 and > 1.15 µg mL −1 (therapeutic indexes (SI) of ≥ 3 and < 1, respectively), and are leading candidates for further development.

show abstract

Synthesis, structural characterization and cytotoxic activity of organotin derivatives of indomethacin

Cited by 22 publications

References 29 publications

Novel Organotin(IV) Schiff Base Complexes with Histidine Derivatives: Synthesis, Characterization, and Biological Activity

Novel Organotin(IV) Schiff Base Complexes with Histidine Derivatives: Synthesis, Characterization, and Biological Activity

Tributyltin(IV) Schiff base complexes with amino acid derivatives: synthesis, characterization and biological activity

Synthesis and anti-HIV Activity of New Benzimidazole, Benzothiazole and Carbohyrazide Derivatives of the anti-Inflammatory Drug Indomethacin

Contact Info

Product

Resources

About