Azido analogs of neuroactive steroids

Lukáš Vidrna; Ivan Černý; Vladimír Pouzar; Jiřina Borovská; Vojtěch Vyklický; Ladislav Vyklický Jr; Hana Chodounská

doi:10.1016/j.steroids.2011.04.008

Azido analogs of neuroactive steroids

Steroids. 2011 Sep-Oct;76(10-11):1043-50. doi: 10.1016/j.steroids.2011.04.008. Epub 2011 Apr 25.

Authors

Lukáš Vidrna¹, Ivan Černý, Vladimír Pouzar, Jiřina Borovská, Vojtěch Vyklický, Ladislav Vyklický Jr, Hana Chodounská

Affiliation

¹ Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., 166 10 Prague 6, Czech Republic.

PMID: 21545806
DOI: 10.1016/j.steroids.2011.04.008

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Dioscoreaceae / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Steroids / chemistry*

Substances

Steroids