Allopregnanolone and Pregnanolone Analogues Modified in the C Ring: Synthesis and Activity

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F13%3A00392261" target="_blank" >RIV/61388963:_____/13:00392261 - isvavai.cz</a>

Alternative codes found

RIV/00023752:_____/13:43914448

Result on the web

<a href="http://dx.doi.org/10.1021/jm3016365" target="_blank" >http://dx.doi.org/10.1021/jm3016365</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/jm3016365" target="_blank" >10.1021/jm3016365</a>

Result language

angličtina

Original language name

Allopregnanolone and Pregnanolone Analogues Modified in the C Ring: Synthesis and Activity

Original language description

25R-3 beta-Hydroxy-5 alpha-spirostan-12-one (hecogenin) and 11 alpha-hydroxypregn-4-ene-3,20-dione (11 alpha-hydroxyprogesterone) were used as starting materials for the synthesis of a series of 11- and 12-substituted derivatives of 5 xi-pregnanolone (3alpha-hydroxy-5 alpha-pregnan-20-one and 3 alpha-hydroxy-5 beta-pregnan-20-one), the principal neurosteroid acting via gamma-aminobutyric acid (GABA). These analogues were designed to study the structural requirements of the corresponding GABA(A) receptor. Their biological activity was measured by in vitro test with [H-3]flunitrazepam as radio-ligand in which allopregnanolone and its active analogues stimulated the binding to the GABA(A) receptor. Analysis of the SAR data suggests dependence of the flunitrazepam binding activity on the hydrophobic-hydrophilic balance of the groups at the C-ring edge rather than on specific interactions between them and the receptor.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

FR - Pharmacology and apothecary chemistry

OECD FORD branch

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Project

<a href="/en/project/GAP303%2F12%2F1464" target="_blank" >GAP303/12/1464: Neurosteroid modulation of NMDA receptors</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2013

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Journal of Medicinal Chemistry

ISSN

0022-2623

e-ISSN

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Volume of the periodical

56

Issue of the periodical within the volume

6

Country of publishing house

US - UNITED STATES

Number of pages

14

Pages from-to

2323-2336

UT code for WoS article

000317032200013

EID of the result in the Scopus database

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