179319-84-7

Upstream product

• 67-56-1 methanol 
• 20760-12-7 1-(2-hydroxyphenyl)-3-phenyl-1-propanol 
• 3516-95-8 2'-hydroxy-3-phenylpropiophenone 

Downstream Products

• 179319-72-3 2-[2-(1-Methoxy-3-phenyl-propyl)-phenoxymethyl]-oxirane 

Relevant academic research and scientific papers

Photoreactions of trans-1-o-Hydroxyphenyl-2-phenylcyclopropane

The photochemistry of trans-1-o-hydroxyphenyl-2-phenylcyclopropane, trans-1, was studied under a variety of experimental conditions. Direct irradiation through quartz in cyclohexane gave rise mainly to ring-expanded products, 2-phenyl-3,4-dihydro-2H-benzopyran, 2, 2-benzyl-2,3-dihydrobenzofuran, 3, and 1-o-hydroxyphenylindan, 4. The major products, 2 and 3, are rationalized by intramolecular proton transfer. However, a significant fraction of 3 is formed via ring-opening to cinnamylphenol, 5. An additional product, o-(α-cyclohexylmethyl)phenol, 7, suggests fragmentation of trans-1 and (formal) insertion of o-hydroxyphenylcarbene into cyclohexane. Direct irradiation in methanol produced methanol adducts 8 and 9 instead of 2, 3,4, or 7. Finally, acetone-sensitized irradiation of trans-1 resulted in geometric isomerization to cis-1; this result can be rationalized via a biradical intermediate.

Structural requirements for activity of propafenone-type modulators in P- glycoprotein-mediated multidrug resistance

The sodium channel blocker propafenone and a series of analogs have been identified as effective modulators of P-glyco-protein-mediated multidrug resistance in human tumor cells. A series of closely related structural homologues showed a highly significant correlation between lipophilicity and pharmacological effect. Reduction of the carbonyl group as well as conversion to a methylether led to a remarkable decrease in activity, whereby lipophilicity lost its predictive character as the main determinant for modulator potency. Similarly, the relative positioning of the acyl- and propanolamine side chains also influences activity, so the distance between carbonyl group and nitrogen atom seems important.