965-67-3Relevant articles and documents
A Change from Kinetic to Thermodynamic Control Enables trans-Selective Stereochemical Editing of Vicinal Diols
Gu, Xin,Wendlandt, Alison E.,Zhang, Yu-An
supporting information, p. 599 - 605 (2022/01/03)
Here, we report the selective, catalytic isomerization of cis-1,2-diols to trans-diequatorial-1,2-diols. The method employs triphenylsilanethiol (Ph3SiSH) as a catalyst and proceeds under mild conditions in the presence of a photoredox catalyst and under
Vecuronium bromide position isomer impurity preparation method
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Paragraph 0028; 0030; 0032-0033; 0050; 0052-0053, (2019/01/17)
The invention discloses a vecuronium bromide position isomer impurity preparation method, and relates to the technical field of synthesis and preparation of chemical substances. By taking androstane-2-alkene-17-ketone as a raw material, a vecuronium bromide position isomer impurity is obtained through oxidization, ring opening, quaternary amination, bromination, substitution, reduction and acetylation reaction. The vecuronium bromide position isomer impurity prepared through the preparation method is high in purity and can be used as a contrast.
A new and efficient method for the synthesis of rocuronium bromide
Wu, Xue-Ying,Wang, Yao-Ling,Hai, Li,Gong, Ping,Wu, Yong
, p. 487 - 492 (2017/01/28)
Rocuronium bromide has been used as an aminosteroid non-depolarizing neuromuscular blocker and muscle relaxant. In this work, a new and efficient route for preparing a key intermediate 2β-(4-morpholinyl)-16β-(1-pyrrolidinyl)-5α-androstan-3α,17β-diol (6) was developed through a ring-opening of epoxide followed by introducing and pyrrolidine. Compound 6 can easily provide rocuronium bromide and the overall yield of compound 6 in 5 steps increased to 57.8%, which was higher than currently reported methods. Extraordinarily, this method would avoid the generation of disubstituted impurities E and F which are difficult to remove.
Novel method for preparing rocuronium bromide
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Paragraph 0011; 0012, (2017/11/18)
The invention relates to a novel method for preparing rocuronium bromide 1-[17beta-acetoxyl-3alpha-hydroxyl-2beta-(4-morpholinyl)-androstane-16beta-yl]-1-(2-propenyl) pyrrole bromide, the problem of chemoselectivity of pyrrolidine open epoxy in an original line is solved, generation of byproducts is avoided, reaction yield is greatly improved, the production cost is reduced, column chromatography separation is avoided, and aftertreatment purification is implemented easily.
NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
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Page/Page column 72; 73, (2015/02/02)
Described herein are neuroactive steroids of the Formula (I): (Formula (I)) or a pharmaceutically acceptable salt thereof; wherein R1a and R1b 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.
Neurosteroid analogues. 18. Structure-activity studies of ent-steroid potentiators of γ-aminobutyric acid type a receptors and comparison of their activities with those of alphaxalone and allopregnanolone
Qian, Mingxing,Krishnan, Kathiresan,Kudova, Eva,Li, Ping,Manion, Brad D.,Taylor, Amanda,Elias, George,Akk, Gustav,Evers, Alex S.,Zorumski, Charles F.,Mennerick, Steven,Covey, Douglas F.
, p. 171 - 190 (2014/02/14)
A model of the alignment of neurosteroids and ent-neurosteroids at the same binding site on γ-aminobutyric acid type A (GABAA) receptors was evaluated for its ability to identify the structural features in ent-neurosteroids that enhance their activity as positive allosteric modulators of this receptor. Structural features that were identified included: (1) a ketone group at position C-16, (2) an axial 4α-OMe group, and (3) a C-18 methyl group. Two ent-steroids were identified that were more potent than the anesthetic steroid alphaxalone in their threshold for and duration of loss of the righting reflex in mice. In tadpoles, loss of righting reflex for these two ent-steroids occurs with EC50 values similar to those found for allopregnanolone. The results indicate that ent-steroids have considerable potential to be developed as anesthetic agents and as drugs to treat brain disorders that are ameliorated by positive allosteric modulators of GABA A receptor function.
NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF
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Page/Page column 111, (2014/01/08)
Described herein are neuroactive steroids of the Formula (I) or a pharmaceutically acceptable salt, solvate, stereoisomer, tautomer, and/or isotopic variant thereof; wherein ----, X, Z1, Z2, R1, R2, R3, and R4 are as defined herein, provided at least one of R1, R2, R3, and X a group of the formula -OC(=O)RE1. Such compounds are envisioned, in certain embodiments, to behave as soft drugs and, in certain embodiments, 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.
New structure-activity relationships of A-and D-ring modified steroidal aromatase inhibitors: Design, synthesis, and biochemical evaluation
Varela, Carla,Tavares Da Silva, Elisiário J.,Amaral, Cristina,Correia Da Silva, Georgina,Baptista, Teresa,Alcaro, Stefano,Costa, Giosuè,Carvalho, Rui A.,Teixeira, Natércia A. A.,Roleira, Fernanda M. F.
experimental part, p. 3992 - 4002 (2012/07/30)
A- and D-ring androstenedione derivatives were synthesized and tested for their abilities to inhibit aromatase. In one series, C-3 hydroxyl derivatives were studied leading to a very active compound, when the C-3 hydroxyl group assumes 3β stereochemistry (1, IC50 = 0.18 μM). In a second series, the influence of double bonds or epoxide functions in different positions along the A-ring was studied. Among epoxides, the 3,4-epoxide 15 showed the best activity (IC50 = 0.145 μM) revealing the possibility of the 3,4-oxiran oxygen resembling the C-3 carbonyl group of androstenedione. Among olefins, the 4,5-olefin 12 (IC50 = 0.135 μM) revealed the best activity, pointing out the importance of planarity in the A,B-ring junction near C-5. C-4 acetoxy and acetylsalicyloxy derivatives were also studied showing that bulky substituents in C-4 diminish the activity. In addition, IFD simulations helped to explain the recognition of the C-3 hydroxyl derivatives (1 and 2) as well as 15 within the enzyme.
2-(N-SUBSTITUTED PIPERAZINYL) STEROID DERIVATIVES
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Page/Page column 53; 90, (2010/06/17)
Novel chemical agents of Formula I are described herein. More specifically, 2-(N-substituted piperazinyl) pregnane and 2-(N-substituted piperazinyl) androstane derivatives exhibiting cytotoxicity on a variety of cancer cell lines are disclosed herein. (I)
The Transannular Effect of One Androstane Epoxide on the Stereochemistry of a Second Epoxidation
Hanson, James R.,Hitchcock, Peter B.,Kiran, Ismail
, p. 2365 - 2383 (2007/10/03)
The transannular directing effect of a 2α,3α-, 2β,3β- and 5α,6α-epoxide on the epoxidation of a 5-ene and a 2-ene respectively has been shown to increase the proportion of epoxidation of the anti face of the alkene when compared to the unsubstituted 2- and 5-androstenes.
