5-Bromobarbituric Acid : A Mild and Selective Monobrominating Agent Employed in the Synthesis of the Gastrin Antagonist GR174152

Bright, Robert D.; Coote, Steven J.; Freeman, Stephen; Hayes, Doug; Smith, G.F.; Tapolczay, David J.

doi:10.1080/00397919608004658

Cited by 6 publications

(2 citation statements)

References 17 publications

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“…135, can be classified as Freidinger lactam analogs [108]. Cote et al later published a synthetic route leading to 136, a powerful suppressor of gastric acid secretion, potentially applicable to the treatment of gastrooesopheageal reflux disease (GORD) [109] (Fig. 11).…”

Section: Cholecystokinin (Cck) and Gastrin Receptor Modulatorsmentioning

confidence: 99%

The Application of Freidinger Lactams and their Analogs in the Design of Conformationally Constrained Peptidomimetics

Perdih¹,

Kikelj

2006

CMC

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Peptides exist in solution as an equilibrium mixture of conformers. The backbone conformational constraints are of interest as a means of limiting degrees of freedom and thereby constraining a synthetic peptide into the bioactive conformation. This concept plays an important role in the design of peptidomimetics in the drug development process. In the early eighties, Freidinger proposed the concept of protected lactam-bridged dipeptides, which was a milestone in the design of conformationally constrained peptides. These types of compounds, now widely known as Freidinger lactams, have been of interest to many medicinal and peptide chemists. This review seeks to present the various applications that Freidinger lactams and their hetero-, fused- and unsaturated analogs have found in the design of conformationally constrained peptidomimetics in different therapeutic areas.

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Section: Cholecystokinin (Cck) and Gastrin Receptor Modulatorsmentioning

confidence: 99%

The Application of Freidinger Lactams and their Analogs in the Design of Conformationally Constrained Peptidomimetics

Perdih¹,

Kikelj

2006

CMC

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“…With an efficient in situ synthesis in hand, we turned our attention to catalytic asymmetric ketene brominations, screening a number of reagents for this purpose (NBS, an obvious choice, is inactive in these applications) . We found that the polybrominated p -quinone 2,4,4,6-tetrabromo-2,5-cyclohexadien-1-one 4 works best in the reaction (eq 1).…”

mentioning

confidence: 99%

Reactive Ketenes through a Carbonate/Amine Shuttle Deprotonation Strategy: Catalytic, Enantioselective α-Bromination of Acid Chlorides

et al. 2001

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ChemInform Abstract: 5‐Bromobarbituric Acid: A Mild and Selective Monobrominating Agent Employed in the Synthesis of the Gastrin Antagonist GR174152.

et al. 1997

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5-Bromobarbituric Acid : A Mild and Selective Monobrominating Agent Employed in the Synthesis of the Gastrin Antagonist GR174152

Cited by 6 publications

References 17 publications

The Application of Freidinger Lactams and their Analogs in the Design of Conformationally Constrained Peptidomimetics

The Application of Freidinger Lactams and their Analogs in the Design of Conformationally Constrained Peptidomimetics

Reactive Ketenes through a Carbonate/Amine Shuttle Deprotonation Strategy: Catalytic, Enantioselective α-Bromination of Acid Chlorides

ChemInform Abstract: 5‐Bromobarbituric Acid: A Mild and Selective Monobrominating Agent Employed in the Synthesis of the Gastrin Antagonist GR174152.

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