Nucleophilic substitution of halogen in 4-halo genated derivatives of glutamic acid

Краснов, В. П.; Koroleva, M. A.; Evstigneeva, N. G.; Низова, И. А.

doi:10.1007/bf00698493

Cited by 4 publications

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“…The different reactivity between tosylate 24 and 25 is not surprising. Krasnov and his colleagues investigated the nucleophilic substitution of two stereoisomers of 4-bromo substituted glutamate derivatives (Scheme ). , First, they found that this type of reaction follows a “rigorous” S N 2 mechanism, that is, a full inversion at the C4 position. Second, the bromide 31 ( erythro ) showed higher reactivity compared to the other stereoisomer, 30 ( threo ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Optically Pure 4-Fluoro-Glutamines as Potential Metabolic Imaging Agents for Tumors

et al. 2010

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A versatile synthetic route to prepare all four stereoisomeric 4-fluoro-glutamines was developed by exploiting a Passerini three-component reaction. The skeleton of 4-substituted glutamine derivatives was efficiently constructed. Subsequent four-step reactions, highlighted by a "neutralized" TASF fluorination, provided the desired products with high yields and excellent optical purity. The optically pure fluorine-18 labeled 4-fluoroglutamines were also successfully prepared using either a 18-crown-6/KHCO(3) or K[222]/K(2)CO(3) catalysis system. Preliminary cell uptake and inhibition studies using the 9L tumor cells and SF188(Bcl-xL) tumor cells (a glutamine addicted tumor derived from glioblastoma) provided strong evidence for their potential application in conjunction with positron emission tomography (PET) for in vivo imaging of tumors, which use glutamine as an alternative energy source.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Optically Pure 4-Fluoro-Glutamines as Potential Metabolic Imaging Agents for Tumors

et al. 2010

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Synthesis of 4‐Amino Derivatives of 5‐Oxoproline

et al. 2007

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The possibility of obtaining the stereoisomeric derivatives of 5-oxoproline and glutamic acid with a tertiary amino group at C-4, using the nucleophilic substitution of bromine in dimethyl (2S,4RS)-4-bromo-N-phthaloylglutamate with secondary amines followed by resolution of diastereomers and removal of protecting groups has been studied. We have shown that the reaction with arylamines results in optically

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Theoretical study of the stereoselectivity in the reaction of 4-haloglutamic acid derivatives with arylamines

Korolyova

Vigorov²,

Краснов³

2022

Russ Chem Bull

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Nucleophilic substitution of halogen in 4-halo genated derivatives of glutamic acid

Cited by 4 publications

References 3 publications

Synthesis of Optically Pure 4-Fluoro-Glutamines as Potential Metabolic Imaging Agents for Tumors

Synthesis of Optically Pure 4-Fluoro-Glutamines as Potential Metabolic Imaging Agents for Tumors

Synthesis of 4‐Amino Derivatives of 5‐Oxoproline

Theoretical study of the stereoselectivity in the reaction of 4-haloglutamic acid derivatives with arylamines

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