256955-84-7Relevant articles and documents
Synthesis of 3α-hydroxy-21-(1′-imidazolyl)-3β-methoxyl- methyl-5α-pregnan-20-one via lithium imidazole with 17α- acetylbromopregnanone
Wong, Fung Fuh,Chen, Chun-Yen,Chen, Tse-Hsin,Huang, Jiann-Jyh,Fang, Hsiao-Ping,Yeh, Mou-Yung
, p. 77 - 82 (2006)
The synthesis of biologically active 3α-hydroxyl-21-(1′- imidazolyl)-3β-methoxymethyl-5α-pregnan-20-one (11) was accomplished in six steps. The key steps were the improvement of stereoselectivity for acetyl isomers in C-17 and the introduction of imidazole into the core structure by use of lithium imidazole. This latter key step provided the desired product 11 in 82% yield without the formation of 1,3-disubstituted imidazolium salt as impurity, which is generally observed in traditional method.
The mechanism investigation in substitution of 21-bromo-3α-hydroxyl-3β-methoxymethyl-5α-pregnan-20-one with nucleophiles
Chen, Chun-Yen,Wong, Fung Fuh,Lee, Yueh-Hsien,Chou, Shan-Yen,Huang, Jiann-Jyh,Yeh, Mou-Yung
, p. 942 - 948 (2006)
A mechanistic study on the nucleophilic substitution of a strictly geometric 21-bromo-3α-hydroxyl-3β-methoxymethyl-5α-pregnan-20-one was described. Reaction of the α-bromoketone with excess lithium imidazole followed by the addition of extra bases including n-butyllithium, methyllithium, lithium piperidine, and lithium pyrrolidine provided unexpected α-nucleophilic carbonyl adducts that derived from strong base. Data from HPLC and proton NMR suggested an epoxide as the intermediate. Two possible reaction pathways were proposed for the nucleophilic substitution reaction. One pathway is the normal SN2 substitution reaction, directly provided the imidazoly product without the formation of the unexpected α-substituted products. The other pathway went through an epoxide intermediate, in which imidazole anion or the strong bases added would attack from the less hindered site of the epoxide to give the substitution product. {A figure is presented}.
COMPOSITIONS AND METHODS FOR TREATING CNS DISORDERS
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Page/Page column 159; 160, (2016/05/24)
Described herein are neuroactive steroids of the Formula (I): or a pharmaceutically acceptable salt thereof; wherein (II), A, R1, R2, R3a, R4a, R4b, R5, R7a, and R7b are as defined herein. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. The present invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia.