Two novel macrocyclic organotin(<scp>iv</scp>) carboxylates based on amide carboxylic acids

Xiao, Xiao; Ling, Yinghui; Mei, Ze-Min; Zhu, Dongsheng; Xu, Lin

doi:10.1039/c3ra46198j

Cited by 23 publications

(13 citation statements)

References 43 publications

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“…As a consequence of the structural differences, similar to macrocycle A in compound 5 , the macrocyclic ring conformation is slightly tiered (Figure S59). Although macrocyclic structures are quite commonly found in organotin complexes, [ 7,82–84 ] so far, there are only few examples for assemblies based on large heteroditopic ligands. [ 5,17,19,21,85 ]…”

Section: Resultsmentioning

confidence: 99%

Triorganotin(IV) derivatives with semirigid heteroditopic hydroxo‐carboxylato ligands: Synthesis, characterization, and cytotoxic properties

Baul

Addepalli

Duthie

et al. 2020

Applied Organom Chemis

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Three organic hydroxy‐carboxylic acids separated by a semirigid aromatic diaza scaffold and carrying alkyl groups of different steric hindrance (H′HL1, cyclopropyl; H′HL2, cyclohexyl; H′HL3, adamantyl) were employed as pro‐ligands. Their reaction with suitable triorganotin precursors leads to 10 complexes of compositions: [Me3Sn(HL1)]n·0.5nC6H5CH3 1, [Et3Sn(HL1)]n 2, [nBu3Sn(HL1)]n 3, [Ph3Sn(HL1)]n 4, [Me3Sn(HL2)]2·2CH2Cl2 5, [Et3Sn(HL2)]2 6, {[nBu3Sn(HL2)][nBu3Sn(HL2)(H2O)]} 7, [Ph3Sn(HL2)]n·nC2H5OH 8, [nBu3Sn(HL3)]n 9, and [Ph3Sn(HL3)]n 10. The solid‐state structures of 1–10 were deduced from single‐crystal X‐ray diffraction studies along with two of the pro‐ligands: H′HL1 and H′HL2. In the solid state, four different extended structure types were observed. In compounds 1–3 with aliphatic substituents at the tin atoms and a small substituent at the ligand backbone (cyclopropyl), 1D coordination polymers based on carboxylate bridging were observed, whereas compounds 4 and 8–10 with large substituents attached to the metal and the ligand (cyclohexyl and adamantyl) were 1D coordination polymers based on heteroditopic binding of the ligands. Albeit having essentially the same ligand conformation, the compounds having smaller substituents at the tin atoms (5, R = Me; 6, R = Et) comprise 24‐membered macrocyclic ring structures. In 7, water molecules are coordinated to half the tin atoms, giving dinuclear fragments {[HL2][nBu3Sn][HL2][nBu3Sn(H2O)]}, which are linked through OwH···Osal hydrogen bonds into 1D hydrogen‐bonded tapes. In solution, the tin atoms in 1–10 are coordinated to a single monoanionic [HL1–3]− ligand molecule utilizing anisobidentate coordination with the carboxylate group, as revealed from 119Sn nuclear magnetic resonance spectral results. The antiproliferative activity of the tri‐n‐butyl and triphenyltin compounds 3, 4, and 7–10 was evaluated against the cervical cancer cells (HeLa) and normal kidney cells (HEK) using the 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide assay. Of these, the adamantyl‐substituted tin complexes 9 and 10 present increased activity with IC50 values of 0.51 ± 0.01 and 0.41 ± 0.03 (μM) and good selectivity. The cell death mechanism was identified as apoptosis based on dual staining with fluorescent dyes (Hoechst 33342/propidium iodide and acridine orange/ethidium bromide) and might be related to reactive oxygen species.

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Section: Resultsmentioning

confidence: 99%

Triorganotin(IV) derivatives with semirigid heteroditopic hydroxo‐carboxylato ligands: Synthesis, characterization, and cytotoxic properties

Baul

Addepalli

Duthie

et al. 2020

Applied Organom Chemis

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“…Fernandes and coworkers synthesized macrocyclic metal complexes and evaluated their ability to scavenge the superoxide anions generated by the xanthine- To further the field of organotin carboxylate macrocycle with aesthetic architecture and to explore the rules of molecular ring formation, we suppose to synthesize novel organotin carboxylate macrocycle with fascinating supramolecular structure. Two unique macrocyclicorganotin(IV)carboxylates were generated by the reactions of dibutyltin oxide with amide dicarboxylic acids and the cell cytotoxicity against mouse sarcoma cells S180 was studied by MTT assays (Xiao et al, 2014). A wide repertoire of Zn(II) complexes have been utilized as radioprotective agents, tumor photosensitizers, antidiabetic insulin-mimetic, and antibacterial or antimicrobial agents (Fig 4).…”

Section: Applications Of Macrocyclic Complexes:-mentioning

confidence: 99%

Macrocyclic Complexes: A New Way Forward Into the Medicinal World.

Chaudhary¹,

Singh²

2016

IJAR

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“…As an important part of organotin chemistry, the study on organotin carboxylate has also been well developed. They own fascinating properties and structures , . It is generally recognized that the structure of organotin carboxylate depends on the ligand type, tin‐R group, and the metal‐to‐ligand molar ratio .…”

Section: Introductionmentioning

confidence: 99%

“…Few have put the attention on the effect of reactive solvent. In fact, the type of reactive solvent can not only affect the coordination of tin atoms in organotin carboxylates occasionally but also influence the internal mechanism of the reaction.…”

Section: Introductionmentioning

confidence: 99%

Organotin Carboxylates based on 3‐(1,3‐Dioxo‐2,3‐dihydro‐1H‐phenalen‐2‐yl)benzoic Acid and the Influence of Solvent on the Molecular Structure

Xiao

Shi

et al. 2017

Zeitschrift anorg allge chemie

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Two novel macrocyclic organotin(iv) carboxylates based on amide carboxylic acids

Cited by 23 publications

References 43 publications

Triorganotin(IV) derivatives with semirigid heteroditopic hydroxo‐carboxylato ligands: Synthesis, characterization, and cytotoxic properties

Triorganotin(IV) derivatives with semirigid heteroditopic hydroxo‐carboxylato ligands: Synthesis, characterization, and cytotoxic properties

Macrocyclic Complexes: A New Way Forward Into the Medicinal World.

Organotin Carboxylates based on 3‐(1,3‐Dioxo‐2,3‐dihydro‐1H‐phenalen‐2‐yl)benzoic Acid and the Influence of Solvent on the Molecular Structure

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