Neurosteroid analogues. 17. Inverted binding orientations of androsterone enantiomers at the steroid potentiation site on γ-aminobutyric acid type A receptors

Journal of Medicinal Chemistry

Volumn 55, Issue 3, 2012, Pages 1334-1345

  Krishnan, Kathiresan ^a   Manion, Brad D ^a   Taylor, Amanda ^a   Bracamontes, John ^a   Steinbach, Joseph H ^a   Reichert, David E ^b   Evers, Alex S ^a   Zorumski, Charles F ^a,b   Mennerick, Steven ^a   Covey, Douglas F ^a  

^a WASHINGTON UNIVERSITY   (United States)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(3ALPHA,11BETA) 3 [[(METHYLOXY)METHYL]OXY] 11 HYDROXYANDROSTAN 17 ONE,CYCLIC 17 (1,2 ETHANEDIYL ACETAL); (3ALPHA,5ALPHA) 3 [[(METHYLOXY)METHYL]OXY]ANDROSTANE 11,17 DIONE,CYCLIC 17 (1,2 ETHANEDIYL ACETAL); (3ALPHA,5ALPHA) 3 HYDROXYANDROSTANE 11,17 DIONE; (3ALPHA,5ALPHA) 3 HYDROXYANDROSTANE 11,17 DIONE,CYCLIC 17 (1,2 ETHANEDIYL ACETAL); (3ALPHA,5ALPHA,11ALPHA) 11 (BENZYLOXY) 3 HYDROXYANDROSTAN 17 ONE; (3ALPHA,5ALPHA,11BETA) 11(BENZYLOXY) 3 [[(METHYLOXY]METHYL]OXY]ANDROSTAN 17 ONE,CYCLIC 17 (1,2 ETHANEDIYL ACETAL); (3ALPHA,5ALPHA,11BETA,17BETA)SPIRO[11 (BENZYLOXY)ANDROSTANE 17,2' OXIRAN] 3 OL; (3ALPHA,5ALPHA,7BETA) 7 (BENZYLOXY) 3 HYDROXYANDROSTAN 17 ONE; (3ALPHA,5ALPHA,7BETA)SPIRO(BENZYLOXY)ANDROSTAN 17,2' OXIRAN] 3 OL; (3BETA) 3 [[(METHYLOXY)METHYL]OXY]ANDROST 5 EN 17 ONE,CYCLIC 17 (1,2 ETHANEDIYL ACETAL); (3BETA) 3 [[(METHYLOXY)METHYL]OXY]ANDROST 5 ENE 7,17 DIONE,CYCLIC 17 (1,2 ETHANEDIYL ACETAL); (3BETA,5ALPHA) 3 [[(METHYLOXY)METHYL]OXY]ANDROSTANE 7,17 DIONE,CYCLIC 17 (1,2 ETHANEDIYL ACETAL); (3BETA,5ALPHA,7BETA) 7 (BENZYLOXY) 3 HYDROXYANDROSTAN 17 ONE; (3BETA,5BETA,7ALPHA,8ALPHA,9BETA,10ALPHA,13ALPHA,14BETA) 7 (BENZYLOXY) 3 HYDROXYANDROSTAN 17 ONE; (3BETA,5BETA,7ALPHA,8ALPHA,9BETA,10ALPHA,13ALPHA,14BETA,17ALPHA)SPIRO[7 (BENZYOXY)ANDROSTANE 17,2' OXIRAN] 3 OL; (3BETA,5BETA,8ALPHA,10ALPHA,13ALPHA,14ALPHA) 3 HYDROXYANDROST 9(11) EN 17 ONE; (3BETA,5BETA,8ALPHA,10ALPHA,13ALPHA,14BETA) 11 (BENZYLOXY) 3 [[(METHYLOXY)METHYL]OXY]ANDROSTAN 17 ONE,CYCLIC 17 (1,2 ETHANEDIYL ACETAL); (3BETA,5BETA,8ALPHA,10ALPHA,13ALPHA,14BETA) 3 [[(METHYLOXY)METHYL]OXY] 11 ANDROSTANE 11,17 DIONE,CYCLIC 17 (1,2 ETHANEDIYL ACETAL); (3BETA,5BETA,8ALPHA,10ALPHA,13ALPHA,14BETA) 3 [[(METHYLOXY)METHYL]OXY] 11 HYDROXYANDROSTAN 17 ONE,CYCLIC 17 (1,2 ETHANEDIYL ACETAL); (3BETA,5BETA,8ALPHA,10ALPHA,13ALPHA,14BETA) 3 [[(METHYLOXY)METHYL]OXY]ANDROST 9(11) EN 17 ONE,CYCLIC 17 (1,2 ETHANEDIYL ACETAL); (3BETA,5BETA,8ALPHA,10ALPHA,13ALPHA,14BETA) 3 HYDROXYANDROST 9(11) EN 17 ONE,CYCLIC 17 (1,2 ETHANEDIYL ACETAL); (3BETA,5BETA,8ALPHA,9BETA,10ALPHA,11ALPHA,13ALPHA,14BETA) 11 (BENZYLOXY) 3 HYDROXYANDROSTAN 17 ONE; (3BETA,5BETA,8ALPHA,9BETA,10ALPHA,11ALPHA,13ALPHA,14BETA,17ALPHA)SPIRO[11 (BENZYLOXY)ANDROSTAN 17,2' OXIRAN] 3 OL; (5BETA,8ALPHA,10ALPHA,13ALPHA,14BETA)ANDROST 9(11)ENE 3,17 DIONE; (5BETA,8ALPHA,10ALPHA,13ALPHA,14BETA,17ALPHA) 17 HYDROXYANDROST 9(11) EN 3 ONE; 4 AMINOBUTYRIC ACID A RECEPTOR; ANDROSTERONE; ANDROSTERONE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALLOSTERISM; ANIMAL EXPERIMENT; ARTICLE; BINDING AFFINITY; DRUG BINDING SITE; DRUG DESIGN; DRUG EFFICACY; DRUG POTENTIATION; ENANTIOMER; NEUROMODULATION; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; TADPOLE;

ALLOSTERIC SITE; ANDROSTERONE; ANIMALS; BINDING, COMPETITIVE; BRAIN; FEMALE; LARVA; MODELS, MOLECULAR; NEUROTRANSMITTER AGENTS; OOCYTES; PATCH-CLAMP TECHNIQUES; PROTEIN BINDING; RADIOLIGAND ASSAY; RATS; RECEPTORS, GABA-A; REFLEX; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; XENOPUS LAEVIS;

EID: 84856900135     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2014925     Document Type: Article

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