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Volumn 52, Issue 7, 2009, Pages 2119-2125

Allopregnanolone (3α-Hydroxy-5α-pregnan-20-one) derivatives with a polar chain in position 16α: Synthesis and activity

Author keywords

[No Author keywords available]

Indexed keywords

16ALPHA BIS(CARBAMOYLOXYMETHYL)METHYL 3ALPHA HYDROXY 5ALPHA PREGNAN 20 ONE; 16ALPHA CARBAMOYLOXYETHYL 3ALPHA HYDROXY 5ALPHA PREGNAN 20 ONE; 16ALPHA ETHYL 20 OXO 5ALPHA PREGNANE 3ALPHA,16B DIYL DICARBAMATE; 16ALPHA ETHYL 20 OXO 5ALPHA PREGNANE 3R,16B DIYL DICARBAMATE; 20,20 ETHYLENEDIOXY 16R BIS(METHOXYCARBONYL)METHYL 5ALPHA PREGNAN 3ALPHA OL; 3ALPHA HYDROXY 16ALPHA (2 HYDROXYETHOXY) 5ALPHA PREGNAN 20 ONE; 3ALPHA HYDROXY 16ALPHA (2,3 DIHYDROXYPROPOXY) 5ALPHA PREGNAN 20 ONE; 3ALPHA HYDROXY 16ALPHA [2 HYDROXY (2 ETHOXYETHOXY)] 5ALPHA PREGNAN 20 ONE; 3ALPHA HYDROXY 16ALPHA BIS(METHOXYCARBONYL)METHYL 5ALPHA PREGNAN 20 ONE; 3ALPHA HYDROXY 16ALPHA METHOXYCARBONYLMETHYL 5ALPHA PREGNAN 20 ONE; 3ALPHA HYDROXY 16ALPHA-BIS(HYDROXYMETHYL)METHYL 5ALPHA PREGNAN 20 ONE; 3ALPHA HYDROXY 5ALPHA PREGNAN 20 ONE; 3ALPHA TERT BUTYLDIMETHYLSILYLOXY 16ALPHA ETHYL 20,20 ETHYLENEDIOXY 5ALPHA PREGNAN 16B OL; 3ALPHA TERT BUTYLDIMETHYLSILYLOXY 20,20 ETHYLENEDIOXY 16ALPHA BIS(HYDROXYMETHYL)METHYL 5ALPHA PREGNANE; 3BETA HYDROXY 16RALPHA (2' HYDROXYETHOXY) PREGN 5 EN 20 ONE; 3R TERT BUTYLDIMETHYLSILYLOXY 20,20 ETHYLENEDIOXY 16R BIS (METHOXYCARBONYL)METHYL 5ALPHA PREGNANE; 4 AMINOBUTYRIC ACID A RECEPTOR; UNCLASSIFIED DRUG; BENZODIAZEPINE RECEPTOR AFFECTING AGENT; DRUG DERIVATIVE; ELTANOLONE;

EID: 64549085335     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801454a     Document Type: Article
Times cited : (6)

References (65)
  • 1
    • 0001027095 scopus 로고    scopus 로고
    • Steroid Modulation of GABAA Receptors
    • Pharmacology of GABA and Glycine Neurotransmission; Möhler, H. Ed, Springer: Berlin
    • Lambert, J. J.; Peters, J. A.; Harney, S. C.; Belelli, D. Steroid Modulation of GABAA Receptors. In Pharmacology of GABA and Glycine Neurotransmission; Möhler, H. Ed.; Handbook of Experimental Pharmacology, Vol. 150; Springer: Berlin, 2001; pp 117-140.
    • (2001) Handbook of Experimental Pharmacology , vol.150 , pp. 117-140
    • Lambert, J.J.1    Peters, J.A.2    Harney, S.C.3    Belelli, D.4
  • 3
    • 30644478785 scopus 로고    scopus 로고
    • Nongenomic effects of estrogen. Why all the uncertainty?
    • Warner, M.; Gustafsson, J. Å. Nongenomic effects of estrogen. Why all the uncertainty? Steroids 2006, 71, 91-95.
    • (2006) Steroids , vol.71 , pp. 91-95
    • Warner, M.1    Gustafsson, J.A.2
  • 4
    • 0038178996 scopus 로고    scopus 로고
    • Whiting, P. J. GABA-A receptor subtypes in the brain, a paradigm for CNS drug discovery. Drug DiscoVery Today 2003, 8, 445-450.
    • Whiting, P. J. GABA-A receptor subtypes in the brain, a paradigm for CNS drug discovery. Drug DiscoVery Today 2003, 8, 445-450.
  • 10
    • 1542327569 scopus 로고    scopus 로고
    • Anticonvulsant activity of the testosterone-derived neurosteroid 3α-androstanediol
    • Reddy, D. S. Anticonvulsant activity of the testosterone-derived neurosteroid 3α-androstanediol. NeuroReport 2004, 15, 515-518.
    • (2004) NeuroReport , vol.15 , pp. 515-518
    • Reddy, D.S.1
  • 11
    • 34548848044 scopus 로고    scopus 로고
    • Neuroactive steroids and human recombinant rho 1 GABA(C) receptors
    • Li, W. J.; Jin, X. C.; Covey, D. F.; Steinbach, J. H. Neuroactive steroids and human recombinant rho 1 GABA(C) receptors. J. Pharmacol. Exp. Ther. 2007, 323, 236-247.
    • (2007) J. Pharmacol. Exp. Ther , vol.323 , pp. 236-247
    • Li, W.J.1    Jin, X.C.2    Covey, D.F.3    Steinbach, J.H.4
  • 12
  • 13
    • 33751314737 scopus 로고    scopus 로고
    • Endogenous neurosteroids regulate GABAA receptors via two discrete transmembrane sites
    • Hosie, A. M.; Wilkins, M. E.; da Silva, H. M. A.; Smart, T. G. Endogenous neurosteroids regulate GABAA receptors via two discrete transmembrane sites. Nature 2006, 444, 486-489.
    • (2006) Nature , vol.444 , pp. 486-489
    • Hosie, A.M.1    Wilkins, M.E.2    da Silva, H.M.A.3    Smart, T.G.4
  • 14
    • 49349099107 scopus 로고    scopus 로고
    • Antidepressant effect and changes of GABA(A) receptor gamma 2 subunit mRNA after hippocampal administration of allopregnanolone in rats
    • Nin, M. S.; Salles, F. B.; Azeredo, L. A.; Frazon, A. P. G.; Gomez, R.; Barros, H. M. T. Antidepressant effect and changes of GABA(A) receptor gamma 2 subunit mRNA after hippocampal administration of allopregnanolone in rats. J. Psychopharmacol. 2008, 22, 477-485.
    • (2008) J. Psychopharmacol , vol.22 , pp. 477-485
    • Nin, M.S.1    Salles, F.B.2    Azeredo, L.A.3    Frazon, A.P.G.4    Gomez, R.5    Barros, H.M.T.6
  • 15
    • 33847415856 scopus 로고    scopus 로고
    • A receptors, relevance to the ovarian cycle and stress
    • A receptors, relevance to the ovarian cycle and stress. J. Neurosci. 2007, 2155-2162.
    • (2007) J. Neurosci , pp. 2155-2162
    • Maguire, J.1    Mody, I.2
  • 17
    • 33646847032 scopus 로고    scopus 로고
    • The pharmacokinetics and interactions of new antiepileptic drugs. An overview
    • Bialer, M. The pharmacokinetics and interactions of new antiepileptic drugs. An overview. Ther. Drug Monit. 2005, 27, 722-726.
    • (2005) Ther. Drug Monit , vol.27 , pp. 722-726
    • Bialer, M.1
  • 18
    • 27844443050 scopus 로고    scopus 로고
    • Valproate is an anti-androgen and anti-progestin
    • Death, A. K.; McGrath, K. C. Y.; Handelsman, D. H. Valproate is an anti-androgen and anti-progestin. Steroids 2005, 70, 946-953.
    • (2005) Steroids , vol.70 , pp. 946-953
    • Death, A.K.1    McGrath, K.C.Y.2    Handelsman, D.H.3
  • 20
    • 58149383668 scopus 로고    scopus 로고
    • Synthesis of the neuroactive steroid antagonist 17-phenyl-5alphaandrost-16-en- 3alpha-ol by a palladium-catalysed coupling reaction
    • Bian, X. Q.; Li, S. S.; Geng, X.; Liu, L. H.; Xie, Z. Y.; Wang, C. Synthesis of the neuroactive steroid antagonist 17-phenyl-5alphaandrost-16-en- 3alpha-ol by a palladium-catalysed coupling reaction. J. Chem. Res., Synop. 2008, 7, 422-424.
    • (2008) J. Chem. Res., Synop , vol.7 , pp. 422-424
    • Bian, X.Q.1    Li, S.S.2    Geng, X.3    Liu, L.H.4    Xie, Z.Y.5    Wang, C.6
  • 21
    • 17444405326 scopus 로고    scopus 로고
    • Neurosteroid analogues. 10. The effect of methyl group substitution at the C-6 and C-7 positions on the GABA modulatory and anesthetic actions of (3alpha,5alpha)- and (3alpha,5beta)-3-hydroxypregnan-20- one
    • Zeng, C. M.; Manion, B. D.; Benz, A.; Evers, A. S.; Zorumski, C. F.; Mennerick, S.; Covey, D. F. Neurosteroid analogues. 10. The effect of methyl group substitution at the C-6 and C-7 positions on the GABA modulatory and anesthetic actions of (3alpha,5alpha)- and (3alpha,5beta)-3-hydroxypregnan-20- one. J. Med. Chem. 2005, 48, 3051-3059.
    • (2005) J. Med. Chem , vol.48 , pp. 3051-3059
    • Zeng, C.M.1    Manion, B.D.2    Benz, A.3    Evers, A.S.4    Zorumski, C.F.5    Mennerick, S.6    Covey, D.F.7
  • 22
    • 64549162656 scopus 로고    scopus 로고
    • SlaVíkoVá et al
    • 2124 Journal of Medicinal Chemistry, 2009, Vol. 52, No. 7 SlaVíkoVá et al.
    • (2009) Journal of Medicinal Chemistry , vol.52 , Issue.7
  • 23
    • 14444270606 scopus 로고    scopus 로고
    • Characterization of the anticonvulsant properties of ganaxolone (CCD 1042; 3alpha-hydroxy-3beta-methyl-5alpha-pregnan-20-one), a selective, high-affinity, steroid modulator of the gamma-aminobutyric acid(A) receptor
    • Carter, R. B.; Wood, P. L.; Wieland, S.; Hawkinson, J. E.; Belelli, D.; Lambert, J. J.; White, H. S.; Wolf, H. H.; Mirsadeghi, S.; Tahir, S. H.; Bolger, M. B.; Lan, N. C.; Gee, K. W. Characterization of the anticonvulsant properties of ganaxolone (CCD 1042; 3alpha-hydroxy-3beta-methyl-5alpha-pregnan-20-one), a selective, high-affinity, steroid modulator of the gamma-aminobutyric acid(A) receptor. J. Pharmacol. Exp. Ther. 1997, 280, 1284-1295.
    • (1997) J. Pharmacol. Exp. Ther , vol.280 , pp. 1284-1295
    • Carter, R.B.1    Wood, P.L.2    Wieland, S.3    Hawkinson, J.E.4    Belelli, D.5    Lambert, J.J.6    White, H.S.7    Wolf, H.H.8    Mirsadeghi, S.9    Tahir, S.H.10    Bolger, M.B.11    Lan, N.C.12    Gee, K.W.13
  • 25
    • 0035824291 scopus 로고    scopus 로고
    • Functional analysis of GABA receptors in nucleus tractus solitarius A neurons from neonatal rats
    • Huang, R. Q.; Dillon, G. H. Functional analysis of GABA receptors in nucleus tractus solitarius A neurons from neonatal rats. Brain Res. 2001, 921, 183-194.
    • (2001) Brain Res , vol.921 , pp. 183-194
    • Huang, R.Q.1    Dillon, G.H.2
  • 26
    • 23844490599 scopus 로고    scopus 로고
    • Š íša, M.; Hniličková, J.; Swaczynová, J.; Kohout, L. Syntheses of new androstane brassinosteroids with 17β-ester groupssbutyrates, heptafluorobutyrates, and laurates. Steroids 2005, 70, 755-762.
    • Š íša, M.; Hniličková, J.; Swaczynová, J.; Kohout, L. Syntheses of new androstane brassinosteroids with 17β-ester groupssbutyrates, heptafluorobutyrates, and laurates. Steroids 2005, 70, 755-762.
  • 27
    • 0034717323 scopus 로고    scopus 로고
    • 6-Substituted derivatives of 7-norallopregnanolone
    • Kasal, A. 6-Substituted derivatives of 7-norallopregnanolone. Tetrahedron 2000, 56, 3559-3565.
    • (2000) Tetrahedron , vol.56 , pp. 3559-3565
    • Kasal, A.1
  • 28
    • 13644271598 scopus 로고    scopus 로고
    • Neurosteroid analogues, synthesis of 6-aza-allopregnanolone
    • Kasal, A.; Matyáš, L.; Buděší nský, M. Neurosteroid analogues, synthesis of 6-aza-allopregnanolone. Tetrahedron 2005, 61, 2269- 2278.
    • (2005) Tetrahedron , vol.61 , pp. 2269-2278
    • Kasal, A.1    Matyáš, L.2    Buděší nský, M.3
  • 30
    • 23044500398 scopus 로고    scopus 로고
    • Drug resistance in brain diseases and the role of drug efflux transporters
    • Löscher, W.; Potschka, H. Drug resistance in brain diseases and the role of drug efflux transporters. Nat. Rev. Neurosci. 2005, 6, 591-602.
    • (2005) Nat. Rev. Neurosci , vol.6 , pp. 591-602
    • Löscher, W.1    Potschka, H.2
  • 31
    • 0142186830 scopus 로고    scopus 로고
    • Pain and the blood-brain barrier, obstacles to obstacles to drug delivery
    • Wolka, A. M.; Huber, J. D.; Davis, T. Pain and the blood-brain barrier, obstacles to obstacles to drug delivery. AdV. Drug DeliVery Rev. 2003, 55, 987-1006.
    • (2003) AdV. Drug DeliVery Rev , vol.55 , pp. 987-1006
    • Wolka, A.M.1    Huber, J.D.2    Davis, T.3
  • 32
    • 3042552746 scopus 로고    scopus 로고
    • Anticonvulsant activity of progesterone and neurosteroids in progesterone receptor knockout mice
    • Reddy, D. S.; Castaneda, D. C.; O'Malley, B. W.; Rogawski, M. A. Anticonvulsant activity of progesterone and neurosteroids in progesterone receptor knockout mice. J. Pharmacol. Exp. Ther. 2004, 310, 230-239.
    • (2004) J. Pharmacol. Exp. Ther , vol.310 , pp. 230-239
    • Reddy, D.S.1    Castaneda, D.C.2    O'Malley, B.W.3    Rogawski, M.A.4
  • 33
    • 28544441523 scopus 로고    scopus 로고
    • Park, K. K.; Ko, D. H.; You, Z.; Heiman, A. S.; Lee, H. J. Synthesis and pharmacological evaluations of new steroidal anti-inflammatory antedrugs, 9α-fluoro-11β,17α,21-trihydroxy-3,20-dioxo-pregna-1, 4-diene-16α-carboxylate (FP16CM) and its derivatives. Steroids 2006, 71, 83-89.
    • Park, K. K.; Ko, D. H.; You, Z.; Heiman, A. S.; Lee, H. J. Synthesis and pharmacological evaluations of new steroidal anti-inflammatory antedrugs, 9α-fluoro-11β,17α,21-trihydroxy-3,20-dioxo-pregna-1, 4-diene-16α-carboxylate (FP16CM) and its derivatives. Steroids 2006, 71, 83-89.
  • 34
    • 0024929342 scopus 로고
    • Synthesis of 17α-acyloxy-9α-fluoro- 11β-hydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 21-thio derivatives and related compounds
    • Mitsukuchi, M.; Ikemoto, T.; Taguchi, M.; Higuchi, S.; Abe, S.; Yasui, H.; Hatayama, K.; Sota, K. Synthesis of 17α-acyloxy-9α-fluoro- 11β-hydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 21-thio derivatives and related compounds. Chem. Pharm. Bull. 1989, 37, 3286-3293.
    • (1989) Chem. Pharm. Bull , vol.37 , pp. 3286-3293
    • Mitsukuchi, M.1    Ikemoto, T.2    Taguchi, M.3    Higuchi, S.4    Abe, S.5    Yasui, H.6    Hatayama, K.7    Sota, K.8
  • 35
    • 0029867856 scopus 로고    scopus 로고
    • Steroid specificity of the human sperm membrane progesterone receptor
    • Alexander, N. J.; Kim, H. K.; Blye, R. R.; Blackmore, P. F. Steroid specificity of the human sperm membrane progesterone receptor. Steroids 1996, 61, 116-125.
    • (1996) Steroids , vol.61 , pp. 116-125
    • Alexander, N.J.1    Kim, H.K.2    Blye, R.R.3    Blackmore, P.F.4
  • 36
    • 0014756898 scopus 로고
    • Pharmaco-chemical interrelations among catatoxic steroids
    • Selye, H. Pharmaco-chemical interrelations among catatoxic steroids. Rev. Can. Biol. 1970, 29, 49-102.
    • (1970) Rev. Can. Biol , vol.29 , pp. 49-102
    • Selye, H.1
  • 37
    • 0033472854 scopus 로고    scopus 로고
    • Epalons, synthesis of new 16α-carboxymethyl derivatives
    • Slavíková, B.; Kasal, A. Epalons, synthesis of new 16α-carboxymethyl derivatives. Collect. Czech. Chem. Commun. 1999, 64, 1479-1486.
    • (1999) Collect. Czech. Chem. Commun , vol.64 , pp. 1479-1486
    • Slavíková, B.1    Kasal, A.2
  • 39
    • 33747881255 scopus 로고    scopus 로고
    • Action of two neuroactive steroids against motor seizures induced by pentetrazol in rats during ontogeny
    • Mareš, P.; Haugvicová, R.; Kasal, A. Action of two neuroactive steroids against motor seizures induced by pentetrazol in rats during ontogeny. Physiol. Res. 2006, 55, 437-444.
    • (2006) Physiol. Res , vol.55 , pp. 437-444
    • Mareš, P.1    Haugvicová, R.2    Kasal, A.3
  • 40
    • 33746917578 scopus 로고    scopus 로고
    • Anticonvulsant action of allopregnanolone in immature rats
    • Mareš, P.; Mikulecká, A.; Haugvicová, R.; Kasal, A. Anticonvulsant action of allopregnanolone in immature rats. Epilepsy Res. 2006, 70, 110-117.
    • (2006) Epilepsy Res , vol.70 , pp. 110-117
    • Mareš, P.1    Mikulecká, A.2    Haugvicová, R.3    Kasal, A.4
  • 41
    • 49749219175 scopus 로고
    • 16-Substituted steroids
    • Mazu, R. H.; Cella, J. A. 16-Substituted steroids. Tetrahedron 1959, 7, 130-137.
    • (1959) Tetrahedron , vol.7 , pp. 130-137
    • Mazu, R.H.1    Cella, J.A.2
  • 42
    • 33645843629 scopus 로고    scopus 로고
    • Organocatalytic oxy-Michael addition of alcohols to α,β-unsaturated aldehydes
    • Kano, T.; Tanaka, Y.; Maruoka, K. Organocatalytic oxy-Michael addition of alcohols to α,β-unsaturated aldehydes. Tetrahedron Lett. 2006, 47, 3039-3041.
    • (2006) Tetrahedron Lett , vol.47 , pp. 3039-3041
    • Kano, T.1    Tanaka, Y.2    Maruoka, K.3
  • 43
    • 33947459181 scopus 로고
    • 17-Hydroxy-20-ketopregnanes from steroidal sapogenins
    • Marker, R. E. 17-Hydroxy-20-ketopregnanes from steroidal sapogenins. J. Am. Chem. Soc. 1949, 71, 4149-4151.
    • (1949) J. Am. Chem. Soc , vol.71 , pp. 4149-4151
    • Marker, R.E.1
  • 45
    • 44349084170 scopus 로고    scopus 로고
    • The oxa-Michael reaction: From recent developments to applications in natural product synthesis
    • Nising, C. F.; Brase, S. The oxa-Michael reaction: from recent developments to applications in natural product synthesis. Chem. Soc. Rev. 2008, 37, 1218-1228.
    • (2008) Chem. Soc. Rev , vol.37 , pp. 1218-1228
    • Nising, C.F.1    Brase, S.2
  • 47
    • 0036134692 scopus 로고    scopus 로고
    • Alumina-promoted fast solid-phase Michael addition of enamines with conjugated enones under microwave irradiation
    • Sharma, U.; Bora, U.; Boruah, R. C.; Sandhu, J. S. Alumina-promoted fast solid-phase Michael addition of enamines with conjugated enones under microwave irradiation. Tetrahedron Lett. 2002, 43, 143-145.
    • (2002) Tetrahedron Lett , vol.43 , pp. 143-145
    • Sharma, U.1    Bora, U.2    Boruah, R.C.3    Sandhu, J.S.4
  • 48
    • 33847803888 scopus 로고    scopus 로고
    • Hajos, Z. G.; Parrish, D. R. Synthesis and conversion of 2-methyl-2-(3-oxobutyl)-1,3-cyclopentanedione to isomeric racemic ketols of [3.2.1]bicyclooctane of perhydroindan series. J. Org. Chem. 1974, 39, 1612-1615.
    • Hajos, Z. G.; Parrish, D. R. Synthesis and conversion of 2-methyl-2-(3-oxobutyl)-1,3-cyclopentanedione to isomeric racemic ketols of [3.2.1]bicyclooctane of perhydroindan series. J. Org. Chem. 1974, 39, 1612-1615.
  • 50
    • 12744280766 scopus 로고    scopus 로고
    • Novel amine-catalysed hydroalkoxylation reactions of activated alkenes and alkynes
    • Murtagh, J. E.; McCooey, S. H.; Connon, S. J. Novel amine-catalysed hydroalkoxylation reactions of activated alkenes and alkynes. Chem. Commun. 2005, 227-229.
    • (2005) Chem. Commun , pp. 227-229
    • Murtagh, J.E.1    McCooey, S.H.2    Connon, S.J.3
  • 51
    • 0141854101 scopus 로고    scopus 로고
    • A general, Brønsted acid-catalyzed hetero-Michael addition of nitrogen, oxygen, and sulfur nucleophiles
    • Wabnitz, T. C.; Spencer, J. B. A general, Brønsted acid-catalyzed hetero-Michael addition of nitrogen, oxygen, and sulfur nucleophiles. Org. Lett. 2003, 5, 2141-2144.
    • (2003) Org. Lett , vol.5 , pp. 2141-2144
    • Wabnitz, T.C.1    Spencer, J.B.2
  • 52
    • 4444296898 scopus 로고    scopus 로고
    • Rhodium-catalyzed addition of alcohols to terminal enones
    • Farnworth, M. V.; Cross, M. J.; Louie, J. Rhodium-catalyzed addition of alcohols to terminal enones. Tetrahedron Lett. 2004, 45, 7441-7443.
    • (2004) Tetrahedron Lett , vol.45 , pp. 7441-7443
    • Farnworth, M.V.1    Cross, M.J.2    Louie, J.3
  • 53
    • 0037140744 scopus 로고    scopus 로고
    • Effect of pressure on sterically congested cyanoalkylation reactions of alcohols
    • Jenner, G. Effect of pressure on sterically congested cyanoalkylation reactions of alcohols. Tetrahedron 2002, 58, 4311-4317.
    • (2002) Tetrahedron , vol.58 , pp. 4311-4317
    • Jenner, G.1
  • 55
    • 37049049736 scopus 로고
    • Side-chain-substituted 5α-pregnanes not carrying substituents in the phenanthrene nucleus
    • Danilewicz, J. B.; Klyne, W. Side-chain-substituted 5α-pregnanes not carrying substituents in the phenanthrene nucleus. J. Chem. Soc. 1962, 4950-4957.
    • (1962) J. Chem. Soc , pp. 4950-4957
    • Danilewicz, J.B.1    Klyne, W.2
  • 56
    • 37049096665 scopus 로고
    • The circular dichroism of strained, bridge-ring, and other ketones
    • Kirk, D. N. The circular dichroism of strained, bridge-ring, and other ketones. J. Chem. Soc., Perkin. Trans. 1 1977, 2122-2148.
    • (1977) J. Chem. Soc., Perkin. Trans. 1 , pp. 2122-2148
    • Kirk, D.N.1
  • 57
    • 24944464209 scopus 로고    scopus 로고
    • Proton modulation of recombinant GABA(A) receptors, influence of GABA concentration and the beta subunit TM2-TM3 domain
    • Wilkins, M. E.; Hosie, A. M.; Smart, T. G. Proton modulation of recombinant GABA(A) receptors, influence of GABA concentration and the beta subunit TM2-TM3 domain. J. Physiol. (London) 2005, 567, 365-377.
    • (2005) J. Physiol. (London) , vol.567 , pp. 365-377
    • Wilkins, M.E.1    Hosie, A.M.2    Smart, T.G.3
  • 58
    • 50249167090 scopus 로고    scopus 로고
    • Synthesis of novel C17 steroidal carbamates. Studies on CYP17 action, androgen receptor binding and function, and prostate cancer cell growth
    • Moreira, V. M. A.; Vasaitis, T. S.; Guo, Z.; Njar, V. C. O.; Salvador, J. A. R. Synthesis of novel C17 steroidal carbamates. Studies on CYP17 action, androgen receptor binding and function, and prostate cancer cell growth. Steroids 2008, 73, 1217-1227.
    • (2008) Steroids , vol.73 , pp. 1217-1227
    • Moreira, V.M.A.1    Vasaitis, T.S.2    Guo, Z.3    Njar, V.C.O.4    Salvador, J.A.R.5
  • 59
    • 0035019780 scopus 로고    scopus 로고
    • Role of glutathione S-transferases A1-1, M1-1, and P1-1 in the detoxification of 2-phenylpropenal, a reactive felbamate metabolite
    • Dieckhaus, C. M.; Roller, S. G.; Santos, W. L.; Sofia, R. D.; Macdonald, T. L. Role of glutathione S-transferases A1-1, M1-1, and P1-1 in the detoxification of 2-phenylpropenal, a reactive felbamate metabolite. Chem. Res. Toxicol. 2001, 14, 511-516.
    • (2001) Chem. Res. Toxicol , vol.14 , pp. 511-516
    • Dieckhaus, C.M.1    Roller, S.G.2    Santos, W.L.3    Sofia, R.D.4    Macdonald, T.L.5
  • 61
    • 10844281990 scopus 로고    scopus 로고
    • Investigating the role of 2-phenylpropenal in felbamate-induced idiosyncratic drug reactions
    • Popovic, M.; Nierkens, S.; Pieters, R.; Uetrecht, J. Investigating the role of 2-phenylpropenal in felbamate-induced idiosyncratic drug reactions. Chem. Res. Toxicol. 2004, 17, 1568-1576.
    • (2004) Chem. Res. Toxicol , vol.17 , pp. 1568-1576
    • Popovic, M.1    Nierkens, S.2    Pieters, R.3    Uetrecht, J.4
  • 63
    • 64549135265 scopus 로고
    • The Michael reaction of 3β-acetoxypregna-5,16-dien-20- one
    • Bladon, P. The Michael reaction of 3β-acetoxypregna-5,16-dien-20- one. J. Chem. Soc. 1958, 372, 3-26.
    • (1958) J. Chem. Soc , vol.372 , pp. 3-26
    • Bladon, P.1


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