Crystal Structure of 2-Thiohydantoin-L-Isoleucine Synthesized under Solvent-Free Conditions

Delgado, Gerzon E.; Seijas, Luis E.; Mora, Asiloé J.; Almeida, Rafael; González, Teresa

doi:10.1080/15421406.2014.928433

Cited by 5 publications

(2 citation statements)

References 19 publications

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“…This lineal packing is also appreciated in the structure of 1-acetyl-5-benzyl-2-thioxoimidazolidin-4-one [19]. The steric bulk of the 2methylpropyl group appears to inhibit formation of rings, as in the structures rac-1-acetyl-5-methyl-2-thioxo-imidazolidin-4-one [18], rac-5-(2methylthio-ethyl)-2-tioxo-imidazolidin-4-one [22], rac-1-acetil-5-propionamida-2-tioxo-imidazolidin-4-ona [24] and (S)-5-secbutyl-2-thiohydantoin [25]. A comparison of these structures suggests increased steric bulk in the 5-position favours chain formation.…”

Section: Bonds N--h•••o and O--h•••o Are Indicated By Dashed Lines H Atoms Not Involved In Hydrogen Bonding Have Been Omitted For Claritymentioning

confidence: 99%

Synthesis, Crystal Structure and Hirshfeld Surface Analysis of 1-Acetyl-5-(2-Methylpropyl)-2-Thioxo-Imidazolidin- 4-One

Chacón

Henao

Jamalis³

et al. 2018

PTQ

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The hydantoin and thiohydantoin heterocycles are present in a wide range of biologically active compounds including therapeutic drugs for the treatment of seizures and anti-tumor compounds. Thiohydantoins, have also been used as anti-convulsant agents and are present in fungicides, herbicides and natural products. However, the principal current interest comes from the application of thiohydantoins for the treatment of prostate cancers. Structural characterization of hydantoin and thiohydantoin are important to comprehend their effect mechanisms because of their considerable biological effects. In this work a thiohydantoin derivative, 1-acetyl-5-(2-methylpropyl)-2-thioxo-imidazolidin-4-one (I), has been obtained by the reaction of 2-amino-4-methylpentanoic acid with KSCN in acetic anhydride-acetic acid mixture. The heterocyclic compound was characterized by FTIR, NMR, powder and single-crystal X-ray diffraction analysis. This compound crystallizes in the triclinic system, space group P-1 (Nº2), Z=4, with two independent molecules in the unit asymmetric. The thiohydantoin (I) forms one-dimensional hydrogen bonded chains, via a single hydrogen bond between the carbonyl oxygens and the amine ring N3 position, that run along [100] direction, with graphset motif C(6). The nature of intermolecular interactions has been analyzed through Hirshfeld surfaces and 2D fingerprint plots.

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Section: Bonds N--h•••o and O--h•••o Are Indicated By Dashed Lines H Atoms Not Involved In Hydrogen Bonding Have Been Omitted For Claritymentioning

confidence: 99%

Synthesis, Crystal Structure and Hirshfeld Surface Analysis of 1-Acetyl-5-(2-Methylpropyl)-2-Thioxo-Imidazolidin- 4-One

Chacón

Henao

Jamalis³

et al. 2018

PTQ

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“…As part of our research work to explore the synthesis and structural characterization of hydantoin and thiohydantoin derivative compounds (Delgado et al, 2007;2012;2013;2015a;2015b;2015c;2016;Sulbaran et al, 2007;Uzcátegui et al, 2009;Seijas et al, 2010;, we have investigated the synthesis, crystalline and molecular structure of rac-2thiohydantoin-valine, systematic name rac-5isopropyl-2-tioxoimidazolidin-4-one, synthesized from a solvent-free reaction.…”

Section: Introductionmentioning

confidence: 99%

SOLVENT-FREE SYNTHESIS AND CRYSTAL STRUCTURE OF rac-2-THIOHYDANTOIN-VALINE

Delgado¹,

Mora²,

González³

et al. 2019

PTQ

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Thiohydantoins have been used in the manufacture of medicines and in industrial processes. Depending on the nature and type of substitution on the heterocyclic ring, these compounds may display pharmaceutical and biological activity with a variety of applications as antiepileptic, antitumoral, antiinflammatory, and principally for the treatment of prostate cancer. In this study, a new thiohydantoin was synthetized from the valine amino acid and structurally characterized. The title compound, C6H10N2O2S, with systematic name rac-5-isopropyl-2-tioxoimidazolidin-4-one, has been synthetized by a solvent-free synthesis. The heterocyclic compound was characterized by spectroscopic infrared (FTIR) and nuclear magnetic resonance (NMR) techniques, powder and single-crystal X-ray diffraction analysis (XRD). This material crystallizes in the monoclinic space group P21/c. In the supramolecular structure, the molecules are joined by N- --H···O and N---H···S hydrogen bonds, forming centrosymmetric R2 2(8) dimers and C2 2(9) chains that run along the [001] direction in an infinite one-dimensional network.

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N-acetyl-5-isopropyl-2-tioxoimidazolidin-4-one: Synthesis, spectroscopic characterization, crystal structure, DFT calculations, Hirshfeld surface analysis and energy framework study

Delgado

Mora

Seijas

et al. 2020

Journal of Molecular Structure

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Crystal Structure of 2-Thiohydantoin-L-Isoleucine Synthesized under Solvent-Free Conditions

Cited by 5 publications

References 19 publications

Synthesis, Crystal Structure and Hirshfeld Surface Analysis of 1-Acetyl-5-(2-Methylpropyl)-2-Thioxo-Imidazolidin- 4-One

Synthesis, Crystal Structure and Hirshfeld Surface Analysis of 1-Acetyl-5-(2-Methylpropyl)-2-Thioxo-Imidazolidin- 4-One

SOLVENT-FREE SYNTHESIS AND CRYSTAL STRUCTURE OF rac-2-THIOHYDANTOIN-VALINE

N-acetyl-5-isopropyl-2-tioxoimidazolidin-4-one: Synthesis, spectroscopic characterization, crystal structure, DFT calculations, Hirshfeld surface analysis and energy framework study

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