ChemInform Abstract: N‐Substituted Hydroxysuccinimides from (S)‐Malic Acid as New Reagents for Asymmetric Diels‐Alder Additions to Enoates.

Poll, Thomas S. van der; Hady, A. F. Abdel; Karge, Reinhard; Linz, G.; Weetman, J.; Helmchen, Günter

doi:10.1002/chin.199020094

Cited by 1 publication

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Due to the marked stereochemical requirements for adenosine receptor affinity exhibited by both agonist and antagonist asymmetric ligands, it became of interest to synthesize the individual enantiomers of 4 and to evaluate their biological activity. From the many known norbornene syntheses based on asymmetric Diels-Alder cycloadditions with dienophiles containing removable chiral auxiliaries, 14 those utilizing (S)-2-hydroxy-N-methylsuccinimde 15 and pantolactone 16 were chosen. They provided the required optically active precursors 5 and 9, respectively, which were treated with aqueous NaOH to remove the chiral auxiliaries (Schemes 1 and 2).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of the Enantiomers of the Potent and Selective A₁-Adenosine Antagonist 1,3-Dipropyl-8-[2-(5,6-epoxynorbonyl)]- xanthine

et al. 1997

View full text Add to dashboard Cite

The individual enantiomers 8 and 12 of the potent and highly selective racemic A1-adenosine antagonist 1,3-dipropyl-8-[2-(5,6-epoxynorbornyl)]xanthine (ENX, 4) were synthesized utilizing asymmetric Diels-Alder cycloadditions for the construction of the norbornane moieties. The absolute configuration of 12 was determined by X-ray crystallography of the 4-bromobenzoate 14, which was derived from the bridged secondary alcohol 13. The latter was obtained from 12 by an acid-catalyzed intramolecular rearrangement. The binding affinities of the enantiomers 8 and 12 and the racemate 4 at guinea pig, rat, and cloned human A1- and A2a-adenosine receptor subtypes were determined. The S-enantiomer 12 (CVT-124) appears to be one of the more potent and clearly the most A1-selective antagonist reported to date, with K1 values of 0.67 and 0.45 nM, respectively, at the rat and cloned human A1-receptors and with 1800-fold (rat) and 2400-fold (human) subtype selectivity. Both enantiomers, administered intravenously to saline-loaded rats, induced diuresis via antagonism of renal A1-adenosine receptors.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of the Enantiomers of the Potent and Selective A₁-Adenosine Antagonist 1,3-Dipropyl-8-[2-(5,6-epoxynorbonyl)]- xanthine

et al. 1997

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: N‐Substituted Hydroxysuccinimides from (S)‐Malic Acid as New Reagents for Asymmetric Diels‐Alder Additions to Enoates.

Abstract: (S)‐Malic acid (I) is cyclized with methylamine (II) to form the N‐methylhydroxysuccinimide (III) which is esterified to produce the acrylates (V).

Cited by 1 publication

References 1 publication

Synthesis and Biological Evaluation of the Enantiomers of the Potent and Selective A₁-Adenosine Antagonist 1,3-Dipropyl-8-[2-(5,6-epoxynorbonyl)]- xanthine

Synthesis and Biological Evaluation of the Enantiomers of the Potent and Selective A₁-Adenosine Antagonist 1,3-Dipropyl-8-[2-(5,6-epoxynorbonyl)]- xanthine

Contact Info

Product

Resources

About

ChemInform Abstract: N‐Substituted Hydroxysuccinimides from (S)‐Malic Acid as New Reagents for Asymmetric Diels‐Alder Additions to Enoates.

Abstract: (S)‐Malic acid (I) is cyclized with methylamine (II) to form the N‐methylhydroxysuccinimide (III) which is esterified to produce the acrylates (V).

Cited by 1 publication

References 1 publication

Synthesis and Biological Evaluation of the Enantiomers of the Potent and Selective A1-Adenosine Antagonist 1,3-Dipropyl-8-[2-(5,6-epoxynorbonyl)]- xanthine

Synthesis and Biological Evaluation of the Enantiomers of the Potent and Selective A1-Adenosine Antagonist 1,3-Dipropyl-8-[2-(5,6-epoxynorbonyl)]- xanthine

Contact Info

Product

Resources

About

Synthesis and Biological Evaluation of the Enantiomers of the Potent and Selective A₁-Adenosine Antagonist 1,3-Dipropyl-8-[2-(5,6-epoxynorbonyl)]- xanthine

Synthesis and Biological Evaluation of the Enantiomers of the Potent and Selective A₁-Adenosine Antagonist 1,3-Dipropyl-8-[2-(5,6-epoxynorbonyl)]- xanthine