cas 485-49-4, (+)-Bicuculline | Articles data ｜lookchem

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485-49-4

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Synthesis, anti-GABA activity and preferred conformation of bicuculline and norbicuculline enantiomers
Synthesis of erythro-(±)-[1SR,9RS]-norbicuculline and threo-(±)-[1SR,9SR]-noradlumidine from piperonal was performed using Bischler-Napieralski cyclization as a key step. Resolution gave rise to (+)-[1S,9R]-norbicuculline ([1S,9R] norBIC) and (-)-[1R,9S]-norbicuculline ([1R,9S] norBIC) in >99.5% enantiomeric purity. Bicuculline enantiomers were readily obtained by methylation of the latter products. [1S,9R]BIC was about 70 times more potent than [1R,9S]BIC as an inhibitor of GABA(A) receptor binding and was about 100 and 900 times more potent than [1S,9R] norBIC at pH 7.1 and 5.0 respectively. Similarly, [1S,9R] norBIC was much less potent than [1S,9R]BIC as an inhibitor of GABA-specific 36Cl- ion flux. The observed increase of about two orders of magnitude in the in vitro biological activity caused by N2-CH3 substitution in [1S,9R] norBIC was attributed to different conformations for erythro- and nor-erythro-bicucullines indicated by 1H nuclear Overhauser enhancements of [1S,9R]BIC and [1S,9R] norBIC.
Kardos,Blandl,Luyen,Doernyei,Gacs-Baitz,Simonyi,Cash,Blasko,Szantay
p. 761 - 765
(1996)
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Haworth,Pinder,Robinson
p. 529
(1950)
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Alkaloids of Corydalis incisa Pers. V. The structures of corydalispirone and corydalisol
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Nonaka,Nishioka
p. 294 - 298
(2007/10/04)

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Chemical Properties

Appearance/Colour :pale yellow solid
Melting Point: 193-197 °C
Boiling Point: 542.3 °C at 760 mmHg
Flash Point:281.8 °C
Density: 1.473 g/cm³
Solubility:Benzene, Chloroform, DMSO, Ethyl Acetate
Storage Temp.:0-6°C
Vapor Pressure: 7.98E-12mmHg at 25°C
Refractive Index: 1.5600 (estimate)
PKA: 4.84(at 25℃)
Merck: 14,1203
BRN: 98786
PSA: 66.46000
LogP: 2.52260

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