Synthesis, photophysical properties and structures of organotin-Schiff bases utilizing aromatic amino acid from the chiral pool and evaluation of the biological perspective of a triphenyltin compound

Baul, Tushar S. Basu; Kehie, Pelesakuo; Duthie, Andrew; Guchhait, Nikhil; Raviprakash, Nune; Mokhamatam, Raveendra B.; Manna, Sunil K.; Armata, Nerina; Scopelliti, Michelangelo; Wang, Ruimin; Englert, Ulli

doi:10.1016/j.jinorgbio.2016.12.001

Cited by 48 publications

(32 citation statements)

References 53 publications

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“…Compared with the reference drug, cis ‐platin (4.80±1.11 μmol/l), complexes 3, 4 , and 5 are more active, and 1 and 2 are not, which are similar to those of our previously reported diorganotin analogues . Compounds 3 – 5 belong to the efficient cytostatic agents, but their activities against HeLa are weaker than triphenyltin and tricyclohexyltin analogues . For 1 – 5 , the activity decreased in the order 4 > 3 > 5 > 2 > 1 (R: Cy > n ‐Bu > Ph > Et > Me), indicating that the organotin moiety play an important role in determining cytotoxicity against cancer cells.…”

Section: Resultssupporting

confidence: 80%

Synthesis, structure and property of diorganotin N‐[(3‐methoxy‐2‐oxyphenyl)methylene]tyrosinates

Tian

Han

Yao

et al. 2018

Applied Organom Chemis

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Five new diorganotin N‐[(3‐methoxy‐2‐oxyphenyl)methylene] tyrosinates, R2Sn[2‐O‐3‐MeOC6H3CH=NCH (CH2C6H4OH‐4)COO] (R = Me, 1; Et, 2; Bu, 3; Cy, 4; Ph, 5), have been synthesized and characterized by elemental analysis, IR, NMR (1H, 13C and 119Sn) spectra, and the X‐ray single crystal diffraction. In non‐coordinated solvent, complexes 1–5 have penta‐coordinated tin atom. In the solid state, 1–3 are centrosymmetric dimmers in which each tin atom is seven‐coordinated in a distorted pentagonal bipyramid, and 4 displays discrete molecular structure with distorted trigonal bipyramidal geometry, and the tin atom of 5 is hexa‐coordinated and possess the distorted octahedral geometry with a coordinational methanol molecule. The intermolecular O‐H⋅⋅⋅O hydrogen bonds in 1–4 link molecules into the different one‐dimensional supramolecular chain with R22 (30) or R22 (20) macrocycles, and the molecules of 5 are joined into a two‐dimensional supramolecular network containing R44 (24) and R44 (28) two macrocycles. Bioassay results against human tumour cell HeLa indicated that 3‐5 belonged to the efficient cytostatic agents and the activity decreased in the order 4>3>5>2>1. The fluorescence determinations show the complexes may be explored for potential luminescent materials.

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Section: Resultssupporting

confidence: 80%

Synthesis, structure and property of diorganotin N‐[(3‐methoxy‐2‐oxyphenyl)methylene]tyrosinates

Tian

Han

Yao

et al. 2018

Applied Organom Chemis

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“…In spite of exhibiting interesting luminescent properties, bioimaging studies of organotin(IV) complexes have been scarcely reported . However, very recently, fluorescence imaging was successfully employed to investigate cytotoxicity of organotin(IV) compounds . Interestingly, Sn(IV) is attached to phenyl (Ph), n ‐butyl ( n ‐Bu) or methyl (Me) groups in these complexes.…”

Section: Introductionmentioning

confidence: 99%

Schiff base supported mononuclear organotin(IV) complexes: Syntheses, structures and fluorescence cell imaging

Vinayak

Dey

Ghosh

et al. 2017

Applied Organom Chemis

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Three mononuclear organotin(IV) complexes supported by Schiff bases have been synthesized. The complexes [(C6H5)2Sn(L)] (1), [(t‐Bu)2Sn(L)] (2) and [(t‐Bu)2Sn(L')] (3) (L, L' = deprotonated Schiff bases) were obtained in good yield by the reaction of Schiff bases H2L or H2L′ with corresponding diorganotin dichlorides respectively. All newly synthesized complexes were characterized by means of FT‐IR spectroscopy, elemental analysis and multinuclear (1H, 13C and 119Sn) NMR spectroscopy. In addition, single crystal X‐ray diffraction analyses were employed to establish the solid state molecular structures of these complexes. The structures of 1–3 reveal that all complexes are mononuclear with a five‐coordinated tin(IV) centre in it. The absorption and emission properties of all complexes have been investigated. Moreover, cytotoxicity and fluorescence cell imaging studies of theses complexes have been performed.

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“…The presence of an imine moiety (‐C=N‐) in the ligand skeleton can greatly influence the biological properties of the metal compounds…”

Section: Synthesis Structure and Anti‐cancer Activity Of Triphenymentioning

confidence: 99%

“…Compound 23 was synthesized by reacting Ph 3 SnCl with the sodium salt of 2‐(( E )‐(( Z )‐4‐hydroxypent‐3‐en‐2‐ylidene) amino)‐3‐(1H‐indol‐3‐yl)propanoate, H 2 NaL 11 (Table , entry 5 and Scheme ) in anhydrous chloroform The compound was designed in order to incorporate, in the same ligand skeleton, imino, carboxylate and indole groups, as well as methyl and hydroxide substituents, which are features, together with the phenyl residues coordinated to the tin(IV) cation, that were considered as adequate for the compound acting as inhibitor for tryptophan 2,3‐dioxygenase. The solid‐state structure of 23 was authenticated by single‐crystal X‐ray diffraction, which revealed its 1D polymeric nature, similar to what was described for 17–22 (see above) The monodentate binding mode of carboxylate in 23 was clearly supported by the value (204 cm –1 ) of the difference (Δ) between the asymmetric and the symmetric vibration modes of the carboxylate group [Δ = ν as(OCO) – ν s(OCO) ] in the IR spectrum.…”

Section: Synthesis Structure and Anti‐cancer Activity Of Triphenymentioning

confidence: 99%

Biological Evaluation of Azo‐ and Imino‐Based Carboxylate Triphenyltin(IV) Compounds

et al. 2020

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Azo (‐N=N‐)‐ and imino (‐C=N‐)‐carboxylate triphenyltin(IV) compounds, which are well known for their promising biological activities, are usually synthesized by reacting a triphenyltin(IV) compound (oxide, hydroxide or chloride) with a suitably substituted carboxylic acid, under appropriate conditions. Their biological properties are influenced by the type/position of the functional azo or imino group in the carboxylate ligand skeleton. They are very effective in anticancer studies, being often better than the standard drug cisplatin in terms of cytotoxicity. A few of the azo‐appended carboxylate triphenyltin(IV) compounds also display anti‐bacterial, anti‐fungal and anti‐diabetic activities. The present manuscript highlights the syntheses, structures, and biological (i.e., anti‐cancer, anti‐bacterial, anti‐fungal and anti‐diabetic) activities of such triphenyltin(IV) compounds.

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Synthesis, photophysical properties and structures of organotin-Schiff bases utilizing aromatic amino acid from the chiral pool and evaluation of the biological perspective of a triphenyltin compound

Cited by 48 publications

References 53 publications

Synthesis, structure and property of diorganotin N‐[(3‐methoxy‐2‐oxyphenyl)methylene]tyrosinates

Synthesis, structure and property of diorganotin N‐[(3‐methoxy‐2‐oxyphenyl)methylene]tyrosinates

Schiff base supported mononuclear organotin(IV) complexes: Syntheses, structures and fluorescence cell imaging

Biological Evaluation of Azo‐ and Imino‐Based Carboxylate Triphenyltin(IV) Compounds

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