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23930-19-0

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NEUROACTIVE STEROIDS AND METHODS OF PREPARATION
Disclosed are neuroactive steroid anaesthetic agents, methods for their preparation and compositions comprising the same. The invention provides scaled up and/or GMP methods for preparing neuroactive steroids, such as alfaxalone, alfadolone and alfadolone acetate.
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(2020/01/31)

Allopregnanolone and pregnanolone analogues modified in the C ring: Synthesis and activity
(25R)-3β-Hydroxy-5α-spirostan-12-one (hecogenin) and 11α-hydroxypregn-4-ene-3,20-dione (11α-hydroxyprogesterone) were used as starting materials for the synthesis of a series of 11- and 12-substituted derivatives of 5ξ-pregnanolone (3α-hydroxy-5α- pregnan-20-one and 3α-hydroxy-5β-pregnan-20-one), the principal neurosteroid acting via γ-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 [3H]flunitrazepam as radioligand in which allopregnanolone and its active analogues stimulated the binding to the GABAA 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.
Slavíková, Barbora,Bujons, Jordi,Matyá?, Libor,Vidal, Miguel,Babot, Zoila,Kri?tofíková, Zdena,Su?ol, Cristina,Kasal, Alexander
p. 2323 - 2336
(2013/06/04)

First synthesis of a C-homosteroid from pregn-4-ene-3,11,20-trione
(3α,5α)-3-Hydroxy-C-homopregnane-11,20-dione (3) was prepared in eleven steps from the commercially available pregn-4-ene-3,11,20-trione (4) via the 11-oxo-13-formyl-12,13-secopregnane intermediate 11 (Scheme 2). Subjection of this secopregnane to an intramolecular aldol condensation afforded the α,β-unsaturated key intermediate C-homopregn-12-en-11-one 12. Copyright
Zhang, Zonglei,Wang, Lizhong,Bian, Xiaoqin,Sun, Qian,Xu, Hangxian,Wang, Cunde
p. 98 - 104
(2011/03/17)

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Chemical Properties

Melting Point: 172-174°
Boiling Point: 468.1 °C at 760 mmHg
Flash Point:251 °C
Density: 1.112 g/cm³
Solubility:chloroform: ≥5 mg/mL, clear, colorless
Storage Temp.:Store at RT
Vapor Pressure: 9.95E-11mmHg at 25°C
Refractive Index: 1.532
PKA: 15.05±0.70(Predicted)
PSA: 54.37000
LogP: 3.77420

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