Highly fluorinated analogues of pharmacologically active compounds

Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39670000293

Abstract

The pentafluorophenyl analogues of noradrenaline, adrenaline, and N-methyladrenaline [C6F5·CH(OH)·CH2·NR1R2 with R1= R2= H; R1= H, R2= Me; R1= R2= Me, respectively] have been prepared by reduction with sodium borohydride of the corresponding amino-ketones obtained by standard methods. 3-(N-2-Chloroethyl-N-ethyl)-aminomethyl-4,5,6,7-tetrafluorobenzo[b]thiophen has also been synthesised as a potential catecholamine antagonist and anti-tumour agent, by a method involving the cyclisation with polyphosphoric acid of 2,3,4,5-tetra-fluorophenylthiopropanone to give the expected 4,5,6,7-tetrafluoro-3-methylbenzo[b]thiophen, and thence by standard methods. The above pentafluorophenyl compounds are only very weak catecholamine antagonists.

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