Call us toll-free

Development of novel hydantoin synthesis

Development of novel hydantoin syntheses

Approximate price

Pages:

275 Words

$19,50

Synthesis of Hydantoins from Enantiomerically Pure α …

This review concerns methods of synthesis, NMR analysis and applications of isotope-labelled hydantoins. The hydantoin moiety is present in natural products and in extraterrestrial ice, indicating this to be an important compound in prebiotic chemistry. Bacterial transport proteins that scavenge hydantoins have been identified, isolated and characterised with isotope-labelling of hydantoins as an essential requirement to achieve this. These are Mhp1 from Microbacterium liquefaciens and PucI from Bacillus subtilis, transporting 5-aryl-substituted hydantoins and allantoin, respectively. The hydantoin ring is a useful centre in synthetic chemistry, especially for combinatorial chemistry, multicomponent reactions and in diversity-oriented synthesis. It is also found in pharmacologically active molecules, such as the anticonvulsant phenytoin. Hydantoins synthesised with isotope labels include hydantoin itself, allantoin, other 5-monosubstituted derivatives, phenytoin, other 5,5-di-substituted derivatives, N-substituted derivatives and other more complex molecules with multiple substituents. Analysis of isotope-containing hydantoins by NMR spectroscopy has been important for confirming purity, labelling integrity, specific activity and molecule conformation. Isotope-labelled hydantoins have been used in a range of biological, biomedical, food and environmental applications including metabolic and in vivo tissue distribution studies, biochemical analysis of transport proteins, identification and tissue distribution of drug binding sites, drug metabolism and pharmacokinetic studies and as an imaging agent.

Hydantoin synthesis - University of Oxford

Figure 11. Synthesis of the separate enantiomers of 5-[2-2H]phenyl-5-phenylhydantoin (3k, 3l) (Scheme 18).

parallel synthesis of a hydantoin ..

This reaction can be performed in excellent yields and is suitable for the synthesis of 5- and 5,5-substituted hydantoins.

Some hydantoins with substituents at the N-1 and/or N-3 position have been synthesised with isotope labels. The hydantoin drug dantrolene (82), which interferes with release of calcium ions from intracellular stores of skeletal muscle, and a photoaffinity azido analogue (83) have been synthesised with a tritium label at a non-exchangeable imine in the N-1 substituent group () [].

Figure 13. Synthesis of other 5,5-disubstituted hydantoins. A 13C-labelled precursor to α-methyldopa (66) (Scheme 20), 5,5-cyclic disubstituted sorbinil with 14C, deuterium or tritium labels (70a, 70b, 70c) (Scheme 21), deuterated and 14C-labelled versions of 5-ethyl-5-phenylhydantoin (71a,71b,71c), [2-13C, 1,3-15N2]spirodihydantoin (74a) (Scheme 22) and a series of 13C,15N-labelled hydantoin sulphonamide compounds (81) (Scheme 23).

Facile synthesis of hydantoins and thiohydantoins in aqueous solution

T1 - Synthesis of substituted 2-imidazolidinones and annelated hydantoins via amidoalkylation transformations

Laure Konnert graduated in Fine and Industrial Organic Chemistry from the Ecole Nationale Supérieure de Chimie de Clermont-Ferrand (now Sigma Clermont) in 2011. After a master degree in 2012 in Organic Synthesis and Chemistry of Bioactive Molecules at the University Claude Bernard Lyon 1, she received her Ph.D. in biomolecular engineering from the University of Montpellier (Institute of Biomolecules Max Mousseron) in 2015, under the direction of Dr. Evelina Colacino and Dr. Frédéric Lamaty as co-director, on the mechanochemical synthesis of amino acid derivatives and hydantoins. She then joined the group of Prof. Carsten Bolm at the Institute of Organic Chemistry in RWTH Aachen University as a postdoctoral researcher in 2016, where she worked on functionalization of lignin by mechanochemistry.

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.

Novel synthetic routes to various hydantoin structures, the advances brought to the classical methods in the aim of producing more sustainable and ...
Order now
  • Synthesis of Hydantoins and Thiohydantoins Spiro …

    The review highlights the hydantoin syntheses presented from the point of view of the preparation methods

  • Synthesis of fused hydantoins by intramolecular ..

    20/12/2017 · [reaction: see text] A fluorous synthesis of hydantoins is introduced

  • Synthesis of Novel 5-(alk-3-enyl)-hydantoins

    AbstractThis review concerns methods of synthesis, NMR analysis and applications of isotope-labelled hydantoins

Order now

Synthesis of Fused Tricyclic Hydantoins of Homotriquinane Type

Figure 10. Synthesis of deuterated and tritiated versions of phenytoin (5,5-diphenylhydantoin) (3) (Schemes 15-17).

A Study on the Synthesis of Hydantoins | Korea Science

Figure 8. Synthesis of isotope-labelled versions of phenytoin (5,5-diphenylhydantoin) (3) (Schemes 10-14).

A Study on the Synthesis of Hydantoins - ..

The hydantoin that has been isotope-labelled and used in biomedical applications with highest proliferation is the anticonvulsant drug phenytoin (5,5-diphenylhydantoin) (3). A wide range of different isotope labels, labelling patterns and synthetic routes have been used with phenytoin and with derivatives of phenytoin.

Synthesis of Hydantoins and Thiohydantoins Spiro-Fused …

Figure 12. Synthesis of 5,5-di-[2-2H]phenylhydantoin (3m) (Scheme 19) and structures of phenytoin derivatives with 125I (61) and 15N,2H labels (62).

The synthesis of 5-substituted hydantoins - CORE

A number of 5-monosubstituted hydantoins have been synthesised with isotope labels, where the label has been directed to the substituent group and/or to the hydantoin moiety. Starting with [1-14C]phenol (12a), 5-(4-methoxy)benzylhydantoin (16) and 5-(4-hydroxy)benzyl-hydantoin (17) were synthesised with a 14C label at the 4-position in the benzyl ring ( Scheme 4) [72].

Urech hydantoin synthesis - Wikipedia

Abstract This review concerns methods of synthesis, NMR analysis and applications of isotope-labelled hydantoins. The hydantoin moiety is present in natural products and in extraterrestrial ice, indicating this to be an important compound in prebiotic chemistry. Bacterial transport proteins that scavenge hydantoins have been identified, isolated and characterised with isotope-labelling of hydantoins as an essential requirement to achieve this. These are Mhp1 from Microbacterium liquefaciens and PucI from Bacillus subtilis, transporting 5-aryl-substituted hydantoins and allantoin, respectively. The hydantoin ring is a useful centre in synthetic chemistry, especially for combinatorial chemistry, multicomponent reactions and in diversity-oriented synthesis. It is also found in pharmacologically active molecules, such as the anticonvulsant phenytoin. Hydantoins synthesised with isotope labels include hydantoin itself, allantoin, other 5-monosubstituted derivatives, phenytoin, other 5,5-di-substituted derivatives, N-substituted derivatives and other more complex molecules with multiple substituents. Analysis of isotope-containing hydantoins by NMR spectroscopy has been important for confirming purity, labelling integrity, specific activity and molecule conformation. Isotope-labelled hydantoins have been used in a range of biological, biomedical, food and environmental applications including metabolic and in vivo tissue distribution studies, biochemical analysis of transport proteins, identification and tissue distribution of drug binding sites, drug metabolism and pharmacokinetic studies and as an imaging agent.

Order now
  • Kim

    "I have always been impressed by the quick turnaround and your thoroughness. Easily the most professional essay writing service on the web."

  • Paul

    "Your assistance and the first class service is much appreciated. My essay reads so well and without your help I'm sure I would have been marked down again on grammar and syntax."

  • Ellen

    "Thanks again for your excellent work with my assignments. No doubts you're true experts at what you do and very approachable."

  • Joyce

    "Very professional, cheap and friendly service. Thanks for writing two important essays for me, I wouldn't have written it myself because of the tight deadline."

  • Albert

    "Thanks for your cautious eye, attention to detail and overall superb service. Thanks to you, now I am confident that I can submit my term paper on time."

  • Mary

    "Thank you for the GREAT work you have done. Just wanted to tell that I'm very happy with my essay and will get back with more assignments soon."

Ready to tackle your homework?

Place an order