595-77-7Relevant articles and documents
Novel stereoids from cetyltrimethylammonium permanganate-initiated oxidative rearrangements of 16-dehydroprogesterone
Kym, Philip R.,Wilson, Scott R.,Gritton, William H.,Katzenellenbogen, John A.
, p. 2833 - 2836 (1994)
Cetyltrimethylammonium permanganate initiates oxidative opening of the D-ring of 16-dehydroprogesterone in CH2Cl2. The novel steroids 3 and 4 have been isolated and characterized as the major products obtained from oxidative rearrangement of the steroid backbone. The X-ray crystal structure of the D-homosteroid 3 is provided, and a putative mechanism that invokes a benzilic acid rearrangement for formation of 3 is presented.
Preparation method of algestone acetophenide
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Paragraph 0023; 0032; 0037; 0042; 0047; 0052; 0054; 0055, (2017/07/21)
The invention discloses a preparation method of algestone acetophenide. The preparation method comprises the following steps: (1) performing reaction among androstenedione cyanohydrin ketal, 1 to 1.5 times amount of substance of phosphorus oxychloride and 1 to 10 times amount of substance of an alkaline medium for 1 to 5h at the reaction temperature of -10 to 80 DEG C to obtain a suppressor; (2) performing reaction between the suppressor and 1 to 10 times amount of substance of methyl magnesium chloride for 1 to 5h at the reaction temperature of -10 to 70 DEG C to obtain a Grignard's product; (3) performing reaction between the Grignard's product and 1 to 5 times amount of substance of potassium permanganate for 10 to 60m at the reaction temperature of -10 to 30 DEG C, and then performing reaction between the Grignard's product and 1 to 5 times amount of substance of acid for 1 to 10h at the reaction temperature of -10 to 30 DEG C to obtain a hydroxy compound; (5) performing reaction among the hydroxy compound, 0.025 to 0.1 time amount of substance of a catalyst and 2 to 10 times amount of substance of acetyl benzene for 1 to 10h at the reaction temperature of -10 to30 DEG C to obtain the algestone acetophenide. Not only the quality and yield of a product are improved, but also the production cost is reduced and the process time is shortened.
Progestin 16α,17α-dioxolane ketals as molecular probes for the progesterone receptor: Synthesis, binding affinity, and photochemical evaluation
Kym,Carlson,Katzenellenbogen
, p. 1111 - 1119 (2007/10/02)
Chemical probes for steroid receptors have proven useful in providing molecular details about important hormone-receptor interactions. A series of progestin 16α,17α-dioxolane ketals of acetophenone or substituted acetophenones that bind to the progesterone receptor (PgR) with comparable or higher affinities than the natural ligand, progesterone, have been prepared and evaluated as potential in vitro and in vivo probes for the progesterone receptor. p-Azidoacetophenone ketal 6, the tetrafluoro analog 8, and the p- (benzoyl)acetophenone ketal 9 demonstrate the required combination of high relative binding affinity (RBA) (6 = 15%, 8 = 14%, 9 = 6.6%, progesterone = 13%, R5020 = 100%) and photoinactivation efficiency (6 = 80%, 8 = 77%, 9 = 29% at 30 min) required for potential photoaffinity labeling reagents for the PgR. The synthesis of azide 6 has been modified to accommodate a palladium- catalyzed tritium gas hydrogenolysis of an iodoaryl precursor in the final stage of the synthetic sequence; this procedure has been verified by hydrogenation. In addition, the progestin p-fluoroacetophenone ketal 10 was selected for preparation in fluorine-18-labeled form, on the basis of its high affinity for the PgR (RBA = 53%). Fluorine-18-labeled progestins may be evaluated as potential diagnostic imaging agents for PgR-positive breast tumors. The radiochemical syntheses and further biochemical results with the fluorine-18-labeled ketal 10 and the tritium-labeled aryl azide 6 will be presented in an accompanying paper and elsewhere.
