976-70-5

Usage

Uses

Used in Pharmaceutical Industry:
3-oxopregn-4-ene-21,17alpha-carbolactone is used as a key intermediate in the synthesis of Canrenone (C175610), an aldosterone antagonist. It plays a crucial role in the development of diuretic medications, which help in the treatment of various conditions related to fluid retention and high blood pressure.
Additionally, due to its steroidal structure, 3-oxopregn-4-ene-21,17alpha-carbolactone may also be utilized in the synthesis of other hormone-related drugs, contributing to the treatment of various endocrine disorders.

Upstream product

• 52520-26-0 (17β)-4',5'-dihydro-5'-methoxyspiro-3-one 
• 35491-69-1 3,3-ethylenedioxy-17β-hydroxy-17α-(2-carboxyethinyl)-androst-5-ene 
• 169306-25-6 3,3-(ethylenedithio)-17α-pregn-4-ene 21,17-carbolactone 
• 57144-06-6 3-methoxyandrosta-3,5-dien-17-one 
• 75219-50-0 C₂₄H₃₄O₄ 
• 50775-60-5 Allyl Tetramethylphosphorodiamidate 
• 972-46-3 3-ethoxyandrosta-3,5-dien-17-one 
• 55542-27-3 17α-(3-hydroxypropyl)-17β-hydroxy-4-androsten-3-one 
• 55542-26-2 17,23-dihydroxy-21,24-dinor-17βH-chol-4-en-20-yn-3-one 
• 63-05-8 Androstenedione 
• 74137-34-1 (8R,9S,10R,13S,14S,17R)-3-Methoxy-10,13-dimethyl-17-((E)-3-trimethylsilanyl-allyl)-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol 
• 74137-33-0 17β-hydroxy-17α-(2,3-epoxy-3-trimethylsilylpropyl)androst-4-en-3-one 
• 74137-32-9 17β-hydroxy-17α-(trimethylsilylprop-2-enyl)androst-4-en-3-one 
• 121936-43-4 5'-hydroxyspiro-5-en-3-one 

Downstream Products

• 976-71-6 canrenone 
• 63815-34-9 6,7-dihydrocanrenonoic acid 
• 52-01-7 SPIRONOLACTONE 
• 976-71-6 Canrenone 

Relevant academic research and scientific papers

Synthesis process of steroid compound, canrenone and spirolactone

The invention relates to the technical field of medicine synthesis, in particular to a synthesis process of a steroid compound, canrenone and spirolactone. An embodiment of the invention provides thesteroid compound. The steroid compound has a structural formula as shown in the specification. In the structural formula, R is selected from H or an alkyl group. The steroid compound can be used for synthesizing canrenone and spirolactone, synthesis conditions are mild, synthesis efficiency is high, the amount of wastewater is small, the quality of the formed products is high, and production costcan be effectively reduced.

A spironolacton intermediate testosterone for synthesizing method

The invention relates to a synthesis method of a chemical medicine, and concretely relates to a synthesis method of a spironolactone intermediate testosterone lactone. The method is characterized in that a compound I 4-androstenedione (4AD) undergoes a two-step reaction of addition siloxane removal and oxidation cyclization to obtain the compound III testosterone lactone, and the reaction route is shown in the specification. Compared with traditional methods adopting a traditional raw material 16-dehydropregnenolone acetate with high price, the method provided by the invention adopting the cheap and easily available 4-androstenedione (4AD, I) as an initial raw material has extremely high production application and economic values under the affection of market supply and demand.

Having a method for the synthesis of intermediates spirondactone

The invention relates to a synthesis method of a chemical medicine, and concretely relates to a synthesis method of a spironolactone intermediate canrenone. The method comprises the following steps: carrying out an ethynylation reaction on a compound I 4-androstenedione (4AD), hydrogenating, carrying out an oxidation cyclization reaction, and carrying out a bromization and debromination reaction to obtain the compound V canrenone, and the above reaction route is shown in the specification. A synthesis method of the structure of an important 21,17-carboxy lactone spiro ring adopted in the invention is different from previous process modes, and is concise and efficient. The method has the characteristics of high yield, good selectivity, low cost, mild reactions, suitableness for industrialization, stability and easy realization.

Steroidal spiro-γ-lactones that inhibit 17β-hydroxysteroid dehydrogenase activity in human placental microsomes

The important enzyme 17β-hydroxysteroid dehydrogenase (17β-HSD) is known to regulate intracellular levels of biologically active steroids, namely, androgens and estrogens. In an effort to develop potent inhibitors of 17β- HSD for reducing the levels of active steroids, we found that steroidal spiro-γ-lactones inhibit 17β-HSD activity. In this report, we describe the synthesis of 11 spiro-γ-lactone analogs containing a steroidal C-18 or C-19 nucleus and compare their relative inhibitory effects on 17γ-HSD activity in the human placenta microsomes that catalyze the interconversion of androgens and estrogens. To avoid the interaction of the cytosolic 17β-HSD activity that is specific for the interconversion of estrone and estradiol, we used 4- androstenedione as substrate. Analysis of the inhibitory effect exerted by these analogs on microsomal 17β-HSD activity indicates that spiro-γ- lactones containing the C-18 nucleus are more potent inhibitors than C-19 nucleus analogs. The best inhibition was obtained with the phenolic spiro- γ-lactone 7 (3-hydroxy-19-nor-17α-pregna-1,3,5(10)-triene 21,17- carbolactone), which has an IC50 value of 0.27 μM, and was much lower than the competitive effect of the unlabeled substrate 4-androstenedione, which has an IC50 value of 1.40 μM. Preincubation with lactone 7 did not inactivate 17β-HSD activity. The results thus suggest that lactone 7 is a reversible inhibitor. Lactone 7 is selective for microsomal 17β-HSD activity, as no inhibition was observed for cytosolic 17β-HSD activity.

STRUCTURE ELUCIDATION OF MINOR COMPONENTS IN DRUGS AND RELATED MATERIALS AFTER HPLC SEPARATION

Four practical examples are presented to demonstrate the usefulness of the off-line coupling of high performance liquid chromatography (HPLC) with various spectroscopic techniques, mainly mass spectrometry.The structure of the decomposition product of the experimental drug 3-chloro-6,9-difluoro-1,3,5-pregnatriene-11β,16α,17,21-tetrahydroxy-16,17-acetonide 21 acetate (RGH-1113) was elucidated by mass spectrometry and UV spectrophotometry.The by-product of the hydroxymethylation of the intermediate 4-methylimidazole was identified by mass spectrometry after HPLC separation.Two impurities in pyridinol carbamate were identified after HPLC separation by the complex application of UV, IR, NMR and mass spectrometry.The origin of both impurities has also been estimated.In the course of the HPLC analysis of the intermediates in the synthesis of spironolactone a side reaction has been detected by means of the mass spectrometric investigation of an isolated by-product .

SILICON IN SYNTHESIS: USE OF THE HIGHLY NUCLEOPHILIC TRIMETHYLSILYLALLYL ANION FOR THE SYNTHESIS OF STEROIDAL 17-SPIRO-γ-LACTONES

Trimethylsilylallylzinc chloride 2 (M = ZnCl) reacts with 17-ketosteroids to give adducts 4 that can be converted into 17-spirolactones.

Silicon in Synthesis. 10. The (Trimethylisilyl)allyl Anion: A β-Acyl Equivalent for the Conversion of Aldehydes and Ketones into γ-Lactones

The (trimethylsilyl)allyl anion reacts with a number of ketones and aldehydes to give adducts 11-21, resulting from the γ mode of ambident reactivity.These adducts were epoxidized to provide the corresponding α,β-epoxysilanes 23-31.Treatment of the epoxysilanes with methanol in the presence of boron trifluoride etherate gave the lactol methyl ethers 32-39.Jones oxidation of the lactol methyl ethers gave γ lactones 40-45.Addition of bromine to the 4-hydroxy vinylsilane derivative 19 gave oxetane 47 which was converted into the compounds 49, 50, and 51.Application of the (trimethylsilyl)allyl anion, as its zinc counterion, to the synthesis of 17-spirosteroidal lactones is described.