152028-96-1

Basic information

• Product Name: iodoproxyfan
• Synonyms: iodoproxyfan
• CAS NO: 152028-96-1
• Molecular Formula: C₁₃H₁₅IN₂O
• Molecular Weight: 342.174
• Mol File: 152028-96-1.mol

Chemical Properties

• Boiling Point: 464.2°Cat760mmHg
• Flash Point: 234.6°C
• Appearance: /
• Density: 1.584g/cm³
• Vapor Pressure: 2.36E-08mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: iodoproxyfan(CAS DataBase Reference)
• NIST Chemistry Reference: iodoproxyfan(152028-96-1)
• EPA Substance Registry System: iodoproxyfan(152028-96-1)

Safety Data

• Hazardous Substances Data: 152028-96-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H15IN2O/c14-12-5-3-11(4-6-12)9-17-7-1-2-13-8-15-10-16-13/h3-6,8,10H,1-2,7,9H2,(H,15,16)

Upstream product

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• 152030-49-4 3-(1-trityl-1H-imidazol-4-yl)propan-1-ol 
• 589-17-3 p-bromobenzyl chloride 
• 183155-67-1 3-<1-(triphenylmethyl)imidazol-4(5)-yl>propyl 4-iodobenzyl ether 

Relevant articles and documents

Iododestannylation: An Improved Synthesis of Iodoproxyfan, a Specific Radioligand of the Histamine H3 Receptor

Iodoproxyfan, a specific radioligand of histamine H3 receptors, was synthesized in 60percent yield under very mild conditions from a tributylstannyl precursor.The arylstannane, which was obtained in a palladium-catalyzed reaction of arylbromide and hexabutylditin, smoothly underwent radioiodination with sodium iodide and chloramine-T to give tritylated iodoproxyfan.Final detritylation was achieved with formic acid 90percent at room temperature.Compared to the original copper(I)-mediated halogen exchange this procedure has major advantages in terms of cost and ease of use. - Key Words: Iodine-125; iododestannylation; iodoproxyfan; histamine H3 receptor antagonist.

Imidazole compounds and their therapeutic applications

A compound selected from the group consisting of a compound of the formulawherein the substituents are defined as in the specification having antagonist properties to histamine H3-receptors.

[125I]iodoproxyfan and related compounds: a reversible radioligand and novel classes of antagonists with high affinity and selectivity for the histamine H3 receptor.

The synthesis and biological evaluation of new histamine H3 receptor antagonists with an iodinated aryl partial structure are described as part of an extensive research program to find model compounds for the development of a new radioligand with high H3 receptor affinity and specific activity. All compounds were tested for their H3 receptor antagonist activity in a [3H]-histamine-release assay with synaptosomes from rat cerebral cortex. The new leads with potent H3 receptor antagonist activity belong to a series of derivatives of 3-(1H-imidazol-4-yl)propanol with carbamate (4-7), ester (8-16), and ether (17-22) as functional groups. Structure-activity relationships are discussed. The most active compound in the functional test (-log Ki = 8.3) and in binding studies with [3H]-(R)-alpha-methylhistamine on rat cerebral cortex (-log Ki = 9.0) in vitro was 3-(1H-imidazol-4-yl)propyl (4-iodophenyl)methyl ether (iodoproxyfan, 19) exhibiting no central H3 receptor antagonist activity in vivo. The potency of iodoproxyfan is more than 300 times lower at H1, H2, alpha1, alpha2, beta1, 5-HT2A, 5-HT3, and M3 receptors than at histamine H3 receptors. Because of the high potency and selectivity of 19, this compound has also been prepared in the [125I]-iodinated form by a nucleophilic halogen exchange reaction using the corresponding bromo derivative 22 as a precursor. The newly prepared [125I]iodoproxyfan (23) possesses advantageous pharmacological properties and fulfills all criteria of a useful radioligand.