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2004
Steroids
U 0300
52- 166
On Steroids. Part 417. Effects of 3α-Amino-5α-pregnan-20-one on GABAA Receptor: Synthesis, Activity and Cytotoxicity. — To gain further insight into possible
functional group modifications in position 3α of the skeleton of the alkaloid funtumin,
various attempts are undertaken in search for the most suitable synthetic approach. The
most benign approach is based on the stereospecific solvolysis of mesyl derivative (III)
to synthesize the 3α-amino target compound (V). Title compound (V) increases the
binding of [3H]flunitrazepam at the GABAA receptor and displays no cytotoxicity at
relevant neuroactive concentrations. This result seems to contradict the hitherto held
axiom of the essentiality of a 3α-hydroxy group for neuronal activity. — (MATYAS,
L.; KASAL*, A.; BABOT RIERA, Z.; SUNOL, C. E.; Collect. Czech. Chem.
Commun. 69 (2004) 7, 1506-1516; Inst. Org. Chem. Biochem., Acad. Sci. Czech Rep.,
CZ-166 10 Prague 6, Czech Republic; Eng.) — H. Hoennerscheid
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