Allylic strain effects on the stereochemistry of the alkylation reaction of mycophenolic acid chiral enolates

Fernández‐Zertuche, Mario; Robledo-Pérez, Ricardo; Meza-Aviña, Ma Elena; Ordoñez-Palacios, Mario

doi:10.1016/s0040-4039(02)00469-0

Cited by 11 publications

(8 citation statements)

References 11 publications

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“…In contrast, approach of the electrophile to enolate 54 (from imide 50 ) is partially hindered by the isopropyl function, resulting in reduced facial preference. A similar alkylation result was observed in the synthesis of mycophenolic acid analogues that was rationalized as being due to 1,3-allylic strain effects on the enolate . As the mixture of alkylated products 51 and 52 were found to be inseparable, an alternate route was devised.…”

Section: Synthesismentioning

confidence: 58%

“…Carrageenan-Induced Thermal Hyperalgesia in the Rat. Thermal hyperalgesia was assessed using the rat plantar test following a modified method . Rats were habituated to the apparatus, which consisted of three individual Perspex boxes on an elevated glass table.…”

Section: Methodsmentioning

confidence: 99%

“…A similar alkylation result was observed in the synthesis of mycophenolic acid analogues that was rationalized as being due to 1,3-allylic strain effects on the enolate. 45 As the mixture of alkylated products 51 and 52 were found to be inseparable, an alternate route was devised.…”

Section: Synthesismentioning

confidence: 99%

“…Thermal hyperalgesia was assessed using the rat plantar test following a modified method. 45 Rats were habituated to the apparatus, which consisted of three individual Perspex boxes on an elevated glass table. A mobile radiant heat source located under the table was focused onto the desired paw, and paw withdrawal latencies (PWL) were recorded.…”

Section: -(1-aminoethyl)-5-methylhexanoic Acid 38mentioning

confidence: 99%

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Structure−Activity Relationships of Pregabalin and Analogues That Target the α₂-δ Protein

et al. 2005

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Pregabalin exhibits robust activity in preclinical assays indicative of potential antiepileptic, anxiolytic, and antihyperalgesic clinical efficacy. It binds with high affinity to the alpha(2)-delta subunit of voltage-gated calcium channels and is a substrate of the system L neutral amino acid transporter. A series of pregabalin analogues were prepared and evaluated for their alpha(2)-delta binding affinity as demonstrated by their ability to inhibit binding of [(3)H]gabapentin to pig brain membranes and for their potency to inhibit the uptake of [(3)H]leucine into CHO cells, a measure of their ability to compete with the endogenous substrate at the system L transporter. Compounds were also assessed in vivo for their ability to promote anxiolytic, analgesic, and anticonvulsant actions. These studies suggest that distinct structure activity relationships exist for alpha(2)-delta binding and system L transport inhibition. However, both interactions appear to play an important role in the in vivo profile of these compounds.

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Section: Synthesismentioning

confidence: 58%

Section: Methodsmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Section: -(1-aminoethyl)-5-methylhexanoic Acid 38mentioning

confidence: 99%

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Structure−Activity Relationships of Pregabalin and Analogues That Target the α₂-δ Protein

et al. 2005

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“…126,127 The trimethoxysilyl group imparts a positive effect on rDA reactions by lowering the activation energy. 128…”

Section: Retro-diels-alder Reactionmentioning

confidence: 99%

The pharmaceutical chemical tendency towards continuous-flow processing

Nekkaa

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The syntheses of various pyrimidinones as potentially bioactive products by means of the highly controlled continuous-flow retro-Diels-Alder reaction of condensed pyrimidinone derivatives are presented. Noteworthy, the use of this approach allowed us to rapidly screen a selection of conditions and quickly confirm the viability of preparing the desired pyrimidinones in short reaction times. Yields typically higher than those published earlier using conventional batch or microwave processes were achieved.

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Seasoning Materials Chemistry by Using a Well‐Matured Organic Concept

Yokoyama

2004

Chemistry A European J

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The concept "introduction of allylic 1,3-strain (A(1,3)-strain) to photochromism" originated from the experience of total synthesis of natural products about 18 years ago, when the author was a post doc. It was first applied to synthetic organic reactions, then it was successfully employed in the diastereoselective photochromic reactions of diarylethenes. A diastereomeric excess of the photoreaction was 88 % for the first example, and it was improved to 94 % by the recent operation of rational molecular tailoring.

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Allylic strain effects on the stereochemistry of the alkylation reaction of mycophenolic acid chiral enolates

Cited by 11 publications

References 11 publications

Structure−Activity Relationships of Pregabalin and Analogues That Target the α₂-δ Protein

Structure−Activity Relationships of Pregabalin and Analogues That Target the α₂-δ Protein

The pharmaceutical chemical tendency towards continuous-flow processing

Seasoning Materials Chemistry by Using a Well‐Matured Organic Concept

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Allylic strain effects on the stereochemistry of the alkylation reaction of mycophenolic acid chiral enolates

Cited by 11 publications

References 11 publications

Structure−Activity Relationships of Pregabalin and Analogues That Target the α2-δ Protein

Structure−Activity Relationships of Pregabalin and Analogues That Target the α2-δ Protein

The pharmaceutical chemical tendency towards continuous-flow processing

Seasoning Materials Chemistry by Using a Well‐Matured Organic Concept

Contact Info

Product

Resources

About

Structure−Activity Relationships of Pregabalin and Analogues That Target the α₂-δ Protein

Structure−Activity Relationships of Pregabalin and Analogues That Target the α₂-δ Protein