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2005
Thiopyran derivatives
R 0370
Synthesis of 8-Thiabicyclo[3.2.1]oct-2-enes and Their Binding Affinity for the
and Serotonin Transporters. — Key compound in the synthesis of thia15- 130 Dopamine
tropenes (VII) is the enol triflate (V), which is subjected to Suzuki coupling with arylboronic acids (VI) to give the targets (VII). Keto ester (III), obtained under standard
conditions, exists in an equilibrium of three isomers, but all optical centers are lost in
the ensuing conversion to (V). Thiatropenes (VII) are highly potent and quite selective
inhibitors of the dopamine transporter. Dichlorophenyl derivative (VIIf) is particularly
potent and selective with regard to inhibition of the seratonin transporter. —
(MELTZER*, P. C.; PHAM-HUU, D.-P.; MADRAS, B. K.; Bioorg. Med. Chem. Lett.
14 (2004) 24, 6007-6010; Organix Inc., Woburn, MA 01801, USA; Eng.) —
H. Hoennerscheid
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