Synthesis and structural characterization of diorganotin(IV) complexes with 2,6‐pyridinedicarboxylic acid

Azadmeher, Amirreza; Amini, Mostafa M.; Hadipour, Nasser L.; Khavasi, Hamid Reza; Fun, Hoong‐Kun; Chen, Chun‐Jung

doi:10.1002/aoc.1343

Cited by 30 publications

(21 citation statements)

References 22 publications

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“…The design and synthesis of new organotin carboxylates by selecting ligands and organotin substrates has been encouraged in order to achieve efficacy. 2,6-pyridinedicarboxylic acid (Scheme 1) is a dicarboxylic acid containing an aromatic N donor atom, and some of its di-and trioganotin derivatives such as R 2 Sn(2,6-C 5 H 3 N)(COO) 2 (H 2 O) (R = Me, n-Bu) (Szorcsik et al, 2004a;Azadmeher et al, 2008), R 2 Sn(2,6-C 5 H 3 N)(COO) 2 (R = t-Bu, Ph, Et) (Gielen, 2002;Szorcsik et al, 2004b), 2,6-C 5 H 3 N(COOSnBu-n 3 ) 2 (Yin et al, 2007), 2,6-C 5 H 3 N(COOSnBu-n 3 ) 2 (4,4′-bpy) (Chandrasekhar et al, 2012) have been studied. In order to continue to expand the chemistry and therapeutic potential of the triorganotin/2,6-pyridinedicarboxylic acid compounds, we synthesized two new bis(triorganotin) 2,6-pyridinedicarboxylates from 2,6-pyridinedicarboxylic acid and triorganotin hydroxide and determined their in vitro cytotoxic activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and in vitro cytotoxic activity of bis(triorganotin) 2,6-pyridinedicarboxylates

Wang

Liu²,

Tian

2014

Main Group Metal Chemistry

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Two bis(triorganotin) 2,6-pyridinedicarboxylates, 2,6-C 5 H 3 N(COOSnR 3 ) 2 (R = C 6 H 11 -c, 1; C 6 H 5 C(CH 3 ) 2 CH 2 , 2), have been synthesized by the reaction of 2,6-pyridinedicarboxylic acid with triorganotin hydroxide in toluene-ethanol and characterized by means of elemental analysis, FT-IR, 1 H NMR spectroscopy, and single crystal X-ray diffraction analysis. In the compounds, a 2,6-pyridinedicarboxylate dianion binds two triorganotin units in a monodentate manner and both tin atoms exist in a distorted tetrahedral environment. Bioassay results have shown that the compounds possess good in vitro cytotoxic activity against two human tumor cell lines, Hela and MCF-7.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and in vitro cytotoxic activity of bis(triorganotin) 2,6-pyridinedicarboxylates

Wang

Liu²,

Tian

2014

Main Group Metal Chemistry

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“…These unusual elongations of the Sn-N bond distances are due to the fact that Snatoms are not symmetrically coordinated to two axial Natoms, but rather to one N-and one O-atom. On the other hand, Sn1 is coordinated to the N-atom from the tbpe ligand (Sn1-N17 = 2.584 Å ), which is longer than the reported values [45][46][47][48][49][50] (Table 4). Thus, the non-equivalence of the tin-nitrogen bond lengths is notable.…”

Section: Resultsmentioning

confidence: 57%

Assembly, Fluorescence Properties and Antitumor Activity of Novel Silver(I) Cyanide Supramolecular Coordination Polymer Based on Trans-1,2-bis(4-pyridyl)ethene and Me3SnCl

Etaiw

El‐din

2011

J Inorg Organomet Polym

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A bimetallic supramolecular coordination polymer; {[(Me 3 Sn) 8 Ag 4 (OH) 4 (CN) 8 (tbpe)](tbpe)} n , 1, was obtained by the reaction in situ of K 2 [Ag(CN) 2 ] with Me 3 SnCl and trans-1,2-bis(4-pyridyl)ethene (tbpe) in a H 2 O/MeCN/NH 3 solvent. The structure of 1 consists of discrete puckered tetranuclear chains comprising {[(Me 3 Sn) 4 Ag 2 (OH) 2 (CN) 4 ] 2 (tbpe)} in addition to one template free tbpe ligand. In these chains, the bridging hydroxyl group and the bipodal tbpe ligand are used to give two novel spacers based on the organometallic Me 3 Sn unit; i.e., a longer spacer [-CN-(Me 3 )Sn-O(H)-(Me 3 )Sn-L-(Me 3 )Sn-O(H)-(Me 3 )Sn-NC-] with a separation distance of 31.29 Å , and a relatively shorter spacer [-CN-(Me 3 )Sn-O(H)-(Me 3 )Sn-NC-] with a separation distance of 14.431 Å .Supramolecular interactions such as hydrogen bonding, p-p stacking, cationÁÁÁp interactions, play a prominent role in the assembly of this compound. The structure of the SCP was also investigated by FTIR and electronic absorption spectra and thermal analysis and the data are compared to the prototype compounds. The SCP 1 exhibits strong fluorescence in acetonitrile and shows specific in vitro antitumor activity against human breast cancer cell line, MCF7.

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“…Among these, acetates, benzoates and salicylates have attracted considerable interest from structural and biological viewpoints [5][6][7][8][9] . Structural diversity observed in metal carboxylates has significant influence of the preparation route on the structure of the final product 10 . ) is too low to account for dissociation reveals non electrolytic nature 15 .…”

Section: Introductionmentioning

confidence: 99%

Transition Metal Chelates of 2-[(2, 6-dichlorophenyl)-amino] Benzene Acetic Acid: Synthesis, Spectral Characterization and Antimicrobial Studies

Kulkarni¹,

Deshpande²

2012

Orientjchem.

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In view of the biochemical activity of transition metal carboxylates is influenced by the molecular structure and coordination status of the metal ion [11][12] , synthesis of transition metal chelates of 2-[(2,6-Dichlorophenyl)amino]benzene acetic acid (DAPA) (Fig. 1.) would be beneficial. Synthesis of metal chelatesCalculated amounts of metal chlorides and ligand DAPA were separately dissolved in ethanol to obtain 0.1M solutions and then clear solutions were mixed in stoichiometric amounts. p H of the mixture was adjusted 6.0 to 7.0 by adding ammonia buffer and resultant mixtures were refluxed on water bath for about 1 to 2 and half hours and allowed to cool. Solid mass separated at the end was separated after digestion, washed with water and ethanol, dried and stored.

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Synthesis and structural characterization of diorganotin(IV) complexes with 2,6‐pyridinedicarboxylic acid

Cited by 30 publications

References 22 publications

Synthesis, characterization and in vitro cytotoxic activity of bis(triorganotin) 2,6-pyridinedicarboxylates

Synthesis, characterization and in vitro cytotoxic activity of bis(triorganotin) 2,6-pyridinedicarboxylates

Assembly, Fluorescence Properties and Antitumor Activity of Novel Silver(I) Cyanide Supramolecular Coordination Polymer Based on Trans-1,2-bis(4-pyridyl)ethene and Me3SnCl

Transition Metal Chelates of 2-[(2, 6-dichlorophenyl)-amino] Benzene Acetic Acid: Synthesis, Spectral Characterization and Antimicrobial Studies

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