title: Azido analogs of neuroactive steroids.
abstract: Analogs of pregnanolone (3α-hydroxy-5β-pregnan-20-one), modified in position 17 were prepared. Compounds with 20-keto pregnane side chain replaced completely by azide (17α- and 17β-azido-5β-androstan-3α-ol), compounds with its part replaced (20-azido-21-nor-5β-pregnan-3α-ol), and compounds with keto group only replaced ((20R)- and (20S)-20-azido-5β-pregnan-3α-ol) were synthesized using tosylate displacements with sodium azide or Mitsunobu reaction with azoimide. All five azido steroids were converted into corresponding sulfates. Subsequent tests for inhibition of glutamate induced response on NMDA receptors revealed that modification of pregnanolone sulfate side chain with azide did not disturb the activity and some of sulfates tested were more active than parent compound.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., 166 10 Prague 6, Czech Republic.
authors.forename: Lukáš
authors.initials: L
authors.lastname: Vidrna
authors.forename: Ivan
authors.initials: I
authors.lastname: Černý
authors.forename: Vladimír
authors.initials: V
authors.lastname: Pouzar
authors.forename: Jiřina
authors.initials: J
authors.lastname: Borovská
authors.forename: Vojtěch
authors.initials: V
authors.lastname: Vyklický
authors.forename: Ladislav
authors.initials: L
authors.lastname: Vyklický
authors.forename: Hana
authors.initials: H
authors.lastname: Chodounská
mesh_terms: D027743:Dioscoreaceae / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013256:Steroids / Q000737:chemistry*
chemical_list: D013256:Steroids