Researches on Phenylhydantoins<sup>1</sup>

Henze, Henry R.; Long, Loren M.

doi:10.1021/ja01852a040

Cited by 16 publications

(13 citation statements)

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“…The intermediate aminonitriles were hydrolyzed in either 6N HCl or concentrated HBr, purified by ion-exchange chromatography and crystallized from an appropriate solvent. The a -alkyl phenylglycines, (RS) -a methyl -3 -carboxy-4-hydroxyphenyl glycine (M3C4HPG), (RS) --ethyl -4 -carboxyphenylglycine (ECPG), (RS)-a-methyl-3carboxymethylphenylglycine (M3CMPG), (RS)-a-methyl-4carboxy-3-chlorophenylglycine (M4C3C1PG), (RS)-a-methyl-2-bromo-4-carboxyphenyl glycine (M2Br4CPG) and (RS)-axmethyl-4-carboxy-3-hydroxyphenylglycine (M4C3HPG), were synthesized from the corresponding acetophenones by the Bucherer-Berg reaction (a variation of the method of Henze & Long, 1941) followed by hydrolysis of the intermediate hydantoins in 6N HCl, purification by ion-exchange chromatography and crystallization from an appropriate solvent.…”

Section: Methodsmentioning

confidence: 99%

Structure‐activity relationships of new agonists and antagonists of different metabotropic glutamate receptor subtypes

Sekiyama

Hayashi

Nakanishi

et al. 1996

British J Pharmacology

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1 We investigated the agonist and antagonist activities of 22 new phenylglycine and phenylalanine derivatives for metabotropic glutamate receptors (mGluRs) by examining their effects on the signal transduction of mGluR1, mGluR2 and mGluR6 subtypes expressed in Chinese hamster ovary cells. This analysis revealed several structural characteristics that govern receptor subtype specificity of the agonist and antagonist activities of phenylglycine derivatives.2 Hydroxyphenylglycine derivatives possessed either an agonist activity on mGluR,/mGluR6 or an antagonist activity on mGluR,.3 Carboxyphenylglycine derivatives showed an agonist activity on mGluR2 but an antagonist activity on mGluR1. 4 a-Methylation or a-ethylation of the carboxyphenylglycine derivatives converts the agonist property for mGluR2 to an antagonist property, thus producing antagonists at both mGluRj and mGluR2.5 Structurally-corresponding phenylalanine derivatives showed little or no agonist or antagonist activity on any subtypes of the receptors. 6 This investigation demonstrates that the nature and positions of side chains and ring substituents incorporated into the phenylglycine structure are critical in determining the agonist and antagonist activities of members of this group of compounds on different subtypes of the mGluR family. 7 We also tested two ax-methyl derivatives of mGluR agonists. (2S, 1'S, 2'S)-2-(2-Carboxycyclopropyl)glycine (L-CCG-I) is a potent agonist for mGluR2 but a-methylation of this compound changes its activity to that of an mGluR2-selective antagonist. In contrast, a-methylation of L-2-amino-4-phosphonobutyrate (L-AP4) results in retention of an agonist activity on mGluR6. Thus, a-methylation produces different effects, depending on the chemical structures of lead compounds and/or on the subtype of mGluR tested.

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Section: Methodsmentioning

confidence: 99%

Structure‐activity relationships of new agonists and antagonists of different metabotropic glutamate receptor subtypes

Sekiyama

Hayashi

Nakanishi

et al. 1996

British J Pharmacology

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“…Most commonly, a mixture of water with ethanol (or methanol) or methanol itself is employed as a solvent, and the one-step reaction products-5-substituted and 5,5-disubstituted hydantoins (unsubstituted on N-1 and N-3)-are typically formed under thermal conditions ( ∼ =50 • C to reflux) or under pressure (sealed vessel) [98,203,. In some cases, amides like fused acetamide, formamide, and dimethylformamide are used as a solvent [6,250,251,256]. Occasionally, the reactions are performed under ultrasonication [8,252,[257][258][259][260][261][262][263][264] or under mechanochemical ball milling using a ZnO catalyst [265].…”

Section: Experimental Conditions 61 General Commentsmentioning

confidence: 99%

“…This reaction works well for aliphatic and aromatic aldehydes or ketones and for cyclic ketones despite some reports concerning the failure of this reaction. For such difficult cases, the use of acetamide (formamide as well as dimethylformamide) as a solvent has been recommended [6,7]. It was found that ultrasonication could also accelerate hydantoin formation [8].…”

Section: Introductionmentioning

confidence: 99%

The Bucherer–Bergs Multicomponent Synthesis of Hydantoins—Excellence in Simplicity

et al. 2021

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Hydantoins and their hybrids with other molecules represent a very important group of heterocycles because they exhibit diverse biological and pharmacological activities in medicinal and agrochemical applications. They also serve as key precursors in the chemical or enzymatic synthesis of significant nonnatural α-amino acids and their conjugates with medical potential. This review provides a comprehensive treatment of the synthesis of hydantoins via the Bucherer–Bergs reaction including the Hoyer modification but limited to free carbonyl compounds or carbonyl compounds protected as acetals (ketals) and cyanohydrins used as starting reaction components. In this respect, the Bucherer–Bergs reaction provides an efficient and simple method in the synthesis of important natural products as well as for the preparation of new organic compounds applicable as potential therapeutics. The scope and limitations, as well as a comparison with some other methods for preparing hydantoins, are also discussed.

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“…Najveći broj sinteza i karakterisanje mnogih hidantoina izveo je Hense i, pri tome, došao do sledećih zaključaka [62][63][64][65]:…”

Section: Uticaj Strukture Na Aktivnost Derivata Hidantoinaunclassified

Hydantoins: Synthesis, properties and anticonvulsant activity

Trišović¹,

Ušćumlić²,

Petrović³

2009

Hem Ind

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Hydantoin is a five-membered cyclic ureide that is present in numerous biologically active compounds including antiarrhytmics, anticonvulsants and antitumor agents. This paper describes different ways of synthesis of hydantoin-derivatives, their physical properties and reactivity. Also, the most widely used hydantoin anticonvulsants and the analysis of structureactivity relationships of anticonvulsant drugs in terms of lipophilicity and hydrogen bonding are presented here

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Researches on Phenylhydantoins¹

Cited by 16 publications

References 0 publications

Structure‐activity relationships of new agonists and antagonists of different metabotropic glutamate receptor subtypes

Structure‐activity relationships of new agonists and antagonists of different metabotropic glutamate receptor subtypes

The Bucherer–Bergs Multicomponent Synthesis of Hydantoins—Excellence in Simplicity

Hydantoins: Synthesis, properties and anticonvulsant activity

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Researches on Phenylhydantoins1

Cited by 16 publications

References 0 publications

Structure‐activity relationships of new agonists and antagonists of different metabotropic glutamate receptor subtypes

Structure‐activity relationships of new agonists and antagonists of different metabotropic glutamate receptor subtypes

The Bucherer–Bergs Multicomponent Synthesis of Hydantoins—Excellence in Simplicity

Hydantoins: Synthesis, properties and anticonvulsant activity

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Researches on Phenylhydantoins¹