Synthesis, DFT calculations and cytotoxic investigation of platinum complexes with 3-thiolanespiro-5′-hydantoin and 4-thio-1H-tetrahydropyranespiro-5′-hydantoin

Bakalova, Adriana; Buyukliev, Rossen; Momekov, Georgi

doi:10.1016/j.molstruc.2015.02.055

Cited by 22 publications

(10 citation statements)

References 24 publications

(37 reference statements)

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“…These findings are in line with our previous reports on the in vitro biological performance of related platinum and palladium species of a different series. 11,12 The complexes 3 and 4 are typical "rulebreaking" compounds, i.e., they do not retain the antitumor properties of the classical platinum therapeutic compounds. 13 C NMR spectra.…”

Section: Resultsmentioning

confidence: 99%

Palladium complexes with 3-methyl-8-thia-1,3-diaza- spiro[4.5]decane-2,4-dione: experimental and theoretical studies

Cherneva¹,

Buyukliev²,

Bakalova³

2018

Arkivoc

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Platinum complexes are a cornerstone of the treatment of various cancers. Their side effects, however, like nephrotoxicity and ototoxicity, have led to the investigation of alternative metal-based anticancer drugs such as palladium complexes, which show promising activities. New cis-palladium complexes with general formulas [PdL 2 Cl 2 ] and [PdL 2 Cl 4 ] and ligand 3-methyl-8-thia-1,3-diaza-spiro[4.5]decane-2,4-dione have been synthesized. The structures of the complexes were elucidated by elemental analyses and spectroscopic techniques as well as theoretical methods. Quantum chemical calculations confirm the square planar geometry of Pd(II) and a distorted octahedral coordination of Pd(IV) complexes. The in vitro cytotoxicity-assay results against K-562 and REH cell lines are also reported.

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Section: Resultsmentioning

confidence: 99%

Palladium complexes with 3-methyl-8-thia-1,3-diaza- spiro[4.5]decane-2,4-dione: experimental and theoretical studies

Cherneva¹,

Buyukliev²,

Bakalova³

2018

Arkivoc

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“…This results in the formation of organometallic complexes (Figure 3), and so hydantoin can adopt mono or bidentate behavior. [43][44] Some of these complexes (27,28) were tested and found to be strong cytotoxic agents.…”

Section: As Ligands In Organometallicmentioning

confidence: 99%

“…Hydantoins, through their nitrogen atoms, have the ability to coordinate with various transition metals such as platinum(II), copper(II), nickel, iron(II), gold(III), cobalt(II), mercury (II), or silver(I) to give organometallic complexes in which hydantoin can adopt mono-or bidentate behavior. 41,42 Some of these complexes (Figure 3; 27 and 28) have been tested and found to be strong cytotoxic agents.…”

Section: Hydantoins As Ligands In Organometallic Complexesmentioning

confidence: 99%

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Kumar¹

2021

Synlett

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Hydantoin and its analogs such as thiohydantoin and iminohydantoin have received substantial attention both from a chemical and biological point of view. Several compounds of this class have shown useful pharmacological activities such as anticonvulsant, antitumor, antiarrhythmic, herbicidal, and others that lead in some cases to clinical applications. Because of broad-spectrum activities, intensive research efforts have been dedicated in industry and academia to the synthesis and structural modifications of hydantoin and its derivatives. Realizing the importance of hydantoin in organic and medicinal chemistry, we also initiated a research program to successfully design and develop the new routes/methods resulting in the formation of hydantoin, thiohydantoin, and iminohydantoin substituted at different positions particularly at the N-1 position without following protection-deprotection strategy. Given the fact that the combination of two or more pharmacophoric groups may lead to hybrid molecules which result in a mixed mechanism of action on the biological target. We, therefore, further extended the developed strategy for the synthesis of new types of hydantoin-based hybrid molecules by combining hydantoin with a triazole, isoxazoline, and phosphate scaffolds as another pharmacophoric group to exploit diverse biological functions.

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“…In this case, the metal ion was coordinated to the sulfur contained in the spiro-compounds, as proved by DFT calculations. 407 5-Methyl-5′-pyridinyl-hydantoin and its derivatives are widely used ligands for the preparation of platinum(II), palladium-(II), 408−413 gold(III), 414 and mercury(II) complexes. 415,416 Depending on the position of the hydantoin core on the pyridinyl ring, 5-methyl-5-pyridylhydantoin could adopt either monodentate or bidentate coordination behavior (Scheme 70).…”

Section: Hydantoins As Ligands In Organometallic Complexesmentioning

confidence: 99%

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

et al. 2017

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The review highlights the hydantoin syntheses presented from the point of view of the preparation methods. Novel synthetic routes to various hydantoin structures, the advances brought to the classical methods in the aim of producing more sustainable and environmentally friendly procedures for the preparation of these biomolecules, and a critical comparison of the different synthetic approaches developed in the last twelve years are also described. The review is composed of 95 schemes, 8 figures and 528 references for the last 12 years and includes the description of the hydantoin-based marketed drugs and clinical candidates.

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Synthesis, DFT calculations and cytotoxic investigation of platinum complexes with 3-thiolanespiro-5′-hydantoin and 4-thio-1H-tetrahydropyranespiro-5′-hydantoin

Cited by 22 publications

References 24 publications

Palladium complexes with 3-methyl-8-thia-1,3-diaza- spiro[4.5]decane-2,4-dione: experimental and theoretical studies

Palladium complexes with 3-methyl-8-thia-1,3-diaza- spiro[4.5]decane-2,4-dione: experimental and theoretical studies

Designed Synthesis of Diversely Substituted Hydantoins and Hydantoin-Based Hybrid Molecules: A Personal Account

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

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