362483-70-3

Upstream product

• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 106-95-6 allyl bromide 

Downstream Products

• 1222181-53-4 methyl 2-(4-bromophenyl)-3-(oxiran-2-yl)-propanoate 
• 362483-84-9 3-(4-bromo-phenyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-dihydro-furan-2-one 
• 362483-88-3 3-(4-bromo-phenyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one 
• 362483-24-7 3-(4-bromophenyl)-5-hydroxymethyl-2,5-dihydrofuran-2-one 
• 362483-77-0 3-(4-bromo-phenyl)-5-hydroxymethyl-dihydro-furan-2-one 
• 301854-29-5 3-(4-bromophenyl)-5-methyltetrahydrofuran-2-one 
• 188943-73-9 2-(4-bromophenyl)pent-4-enoic acid 

Relevant academic research and scientific papers

Macrocycles All Aflutter: Substitution at an Allylic Center Reveals the Conformational Dynamics of [13]-Macrodilactones

The shapes adopted by large-ring macrocyclic compounds play a role in their reactivity and their ability to be bound by biomolecules. We investigated the synthesis, conformational analysis, and properties of a specific family of [13]-macrodilactones as models of natural-product macrocycles. The features of our macrodilactones enabled us to study the relationship between stereogenic centers and planar chirality through the modular synthesis of new members of this family of macrocycles. Here we report on insights gained from a new [13]-macrodilactone that is substituted at a position adjacent to the alkene in the molecule. Analysis of the compound, in comparison to an α-substituted regioisomer, by using X-ray crystallography, NMR coupling constants, and reaction-product characterization in concert with computational chemistry, revealed that the alkene unit is dynamic. That is, the data support a model in which the alkene in our [13]-macrodilactones oscillates between two conformations. A difference in reactivity of one conformation compared to the other leads to manifestation of this dynamic behavior. The results underscore the local conformational dynamics observed in some natural-product macrocycles, which could have implications for biomolecule binding.

Synthesis and structure-antifungal activity relationships of 3-aryl-5-alkyl-2,5-dihydrofuran-2-ones and their carbanalogues: Further refinement of tentative pharmacophore group

Two series of 3-(substituted phenyl)-5-alkyl-2,5-dihydrofuran-2-ones related to a natural product, (-)incrustoporine, were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring exhibited selective antifungal activity against the filamentous strains of Absidia corymbifera and Aspergillus fumigatus. On the other hand, the influence of the lenghth of the alkyl chain at C(5) was marginal. The antifungal effect of the most active compound against the above strains was higher than that of ketoconazole, and close to that of amphotericin B. In order to verify the hypothesis about a possible relationship between the Michael-accepting ability of the compounds and their antifungal activity, a series of simple carbanalogues, 2-(substituted phenyl)cyclopent-2-enones, was prepared and subjected to antifungal activity assay as well.

3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones: Synthesis and biological activity of a novel group of potential antifungal drugs

3-(Substituted phenyl)-5-acyloxymethyl-2H,5H-furan-2-ones related to the natural product (-)-incrustoporine were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring displayed much higher antifungal effect against Aspergillus fumigatus than selected representatives of azole antifungal drugs. In particular, the activity (1.34 μg/mL) of the most promising derivative, 3-(3,4-dichlorophenyl)-5-pivaloyloxymethyl-2H,5H-furan-2-one, was comparable to that of amphotericin B (0.5 μg/mL). Preliminary evaluation of the toxicity of the compound was carried out as well. Considering the size and properties of these molecules in comparison with those of amphotericin B, further development of this novel group of antifungals may lead to substances with better pharmacological profiles than that of the standard anti-Aspergillus drug.

3-Phenyl-5-methyl-2H,5H-furan-2-ones: Tuning antifungal activity by varying substituents on the phenyl ring

A series of racemic 3-phenyl-5-methyl-2H,5H-furan-2-ones related to a natural product, (-)incrustoporine, was synthesized, and their antifungal activity evaluated. The key structural feature, furanone ring, was closed via H2SO4-mediated cyclization of 2-phenylpent-4-enoic acids. The compounds displayed antifungal activity, especially against filamentous fungi. Expressed as the minimum inhibition concentration (MIC) in μmol/L, the activity of the most promising derivative against Absidia corymbifera matched that of ketoconazole (31.25 μmol/L). In terms of μg/mL, the substance was more active (7.6 μg/mL) than this standard antifungal drug (16.6 μg/mL). (C) 2000 Elsevier Science Ltd. All rights reserved.