Synthesis of 2‐n butyl 3‐(3,5‐<sup>125</sup>diiodo 4‐(N, N‐diethylamino 2‐ethoxybenzoyl)) benzofuran hydrochloride (<sup>125</sup>I amiodarone)

Sion, R.

doi:10.1002/jlcr.2580220807

Cited by 3 publications

(1 citation statement)

References 3 publications

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“…Bromination utilized 2 Eq of Br 2 and triethylamine in MeOH at 4°C (Pearson et al, 1967). I 2 and NaI (2 Eq), and 4 Eq of NaOH in water at 65°C gave the diiodinated product after 24 h (Sion, 1985). Sulfuryl chloride (2 Eq) with 0.1% molar equivalent of diisobutylamine in toluene at 60°C gave the dichlorinated product after 2 h (Gnaim and Sheldon, 1995 pK a Measurement.…”

Section: Methodsmentioning

confidence: 99%

A New Class of Cyp2c9 Inhibitors: Probing 2c9 Specificity With High-Affinity Benzbromarone Derivatives

Locuson¹,

Wahlstrom²,

Rock³

et al. 2003

Drug Metab Dispos

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This article is available online at http://dmd.aspetjournals.org ABSTRACT:Noncovalent forces, other than hydrophobic interactions, are important determinants of substrate bias exhibited by some cytochromes P450. The CYP2C9 pharmacophore is proposed to include either an anionic group or hydrogen bond donor in addition to its hydrophobic groups. By constructing analogs of benzbromarone, evidence supporting the existence of a 2C9 anion-binding site was revealed. A nonsubstituted phenol analog was determined to have a pK a of 8.4 and a K i of 414 nM whereas those with dihalogenated benzoyl phenols had pK a values between 4.2 to 5.2 and K i values as low as 1 nM. The nonhalogenated, nonionizable analog is the poorest binder at 796 nM. The K i range covers around three orders of magnitude with even the weakest binder being a more potent inhibitor than 2C9 substrate phenytoin. Thus, benzbromarone derivatives represent a class of molecules with the potential to reveal more structural details of the 2C9 active site.

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Section: Methodsmentioning

confidence: 99%

A New Class of Cyp2c9 Inhibitors: Probing 2c9 Specificity With High-Affinity Benzbromarone Derivatives

Locuson¹,

Wahlstrom²,

Rock³

et al. 2003

Drug Metab Dispos

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Radiohalogen incorporation into organic systems

Bolton

2002

Labelled Comp Radiopharmac

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SummaryThis Review reports the more recent applications of radiohalogen labelling in organic compounds. Modern synthetic methods place more emphasis upon substitution at specific sites. Electrophilic substitution, especially at aromatic carbon atoms, involves displacement of halogen or of metals rather than the earlier popular halogen-deprotiation processes. Nucleophilic displacement, at either aliphatic or aromatic sites, has also become widespread since it may be made more selective by the inclusion of appropriate activating groups or suitable displaced groups. Microwave and thermally induced methods are both reported with a critical assessment of the value of each process.

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Aryl radical involvement in amiodarone-induced pulmonary toxicity: Investigation of protection by spin-trapping nitrones

Nicolescu

Comeau

Hill

et al. 2007

Toxicology and Applied Pharmacology

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Synthesis of 2‐n butyl 3‐(3,5‐¹²⁵diiodo 4‐(N, N‐diethylamino 2‐ethoxybenzoyl)) benzofuran hydrochloride (¹²⁵I amiodarone)

Cited by 3 publications

References 3 publications

A New Class of Cyp2c9 Inhibitors: Probing 2c9 Specificity With High-Affinity Benzbromarone Derivatives

A New Class of Cyp2c9 Inhibitors: Probing 2c9 Specificity With High-Affinity Benzbromarone Derivatives

Radiohalogen incorporation into organic systems

Aryl radical involvement in amiodarone-induced pulmonary toxicity: Investigation of protection by spin-trapping nitrones

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Synthesis of 2‐n butyl 3‐(3,5‐125diiodo 4‐(N, N‐diethylamino 2‐ethoxybenzoyl)) benzofuran hydrochloride (125I amiodarone)

Cited by 3 publications

References 3 publications

A New Class of Cyp2c9 Inhibitors: Probing 2c9 Specificity With High-Affinity Benzbromarone Derivatives

A New Class of Cyp2c9 Inhibitors: Probing 2c9 Specificity With High-Affinity Benzbromarone Derivatives

Radiohalogen incorporation into organic systems

Aryl radical involvement in amiodarone-induced pulmonary toxicity: Investigation of protection by spin-trapping nitrones

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Product

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Synthesis of 2‐n butyl 3‐(3,5‐¹²⁵diiodo 4‐(N, N‐diethylamino 2‐ethoxybenzoyl)) benzofuran hydrochloride (¹²⁵I amiodarone)