28319-79-1

Usage

Uses

Used in Scientific Research:
20-oxopregna-5,7-dien-3-yl acetate is used as a research compound for studying its properties and potential biological activities. Due to the limited information available on its specific uses, it is primarily of interest within scientific research contexts, where it may be investigated for its potential applications in various fields.

Upstream product

• 105186-40-1 3β-acetoxy-7α-bromo-pregn-5-en-20-one 
• 1093959-59-1 3β-hydroxypregn-5-en-20-one-3-acetate 
• 105186-40-1 Acetic acid (3S,8S,9S,10R,13S,14S)-17-acetyl-7-bromo-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 116028-16-1 3β-benzoyloxy-pregna-5,7-dien-20-one 
• 14553-79-8 Δ⁵-pregnene-3β,20(R)-diol 3-O-monoacetate 
• 145-13-1 Pregnenolone 
• 152964-20-0 (20R)-3β-acetoxy-20-hydroxypregna-5,7-diene 
• 81968-78-7 3β-hydroxy-5,7-pregnadien-20-one 
• 108-24-7 acetic anhydride 
• 1778-02-5 Pregnenolone acetate 

Downstream Products

• 85706-88-3 (20S)-20-isopentylamino-9,10-seco-pregna-5,7,10(19)-trien-3β-ol 
• 81968-78-7 3β-hydroxy-5,7-pregnadien-20-one 
• 14646-73-2 3β-acetoxy-5α-pregn-7-en-20-one 
• 1819-14-3 pregnalumisterol 
• 116028-16-1 3β-benzoyloxy-pregna-5,7-dien-20-one 
• 114696-69-4 3β-benzoyloxy-pregna-5,7,9(11)-trien-20-one 

Relevant academic research and scientific papers

Method for synthesizing dydrogesterone

The invention relates to a method for synthesizing a steroid drug dydrogesterone (CAS: 152-62-5). The method comprises the following steps: starting from pregnenolone, carrying out allylic halogenation and elimination to obtain a Pregna-5, 7-dien-3-ol-20-one intermediate; carrying out illumination isomerization to obtain a key intermediate 9 beta, 10 alpha-Pregna-5, 7-dien-3-ol-20-one; then carrying out Oppenauer oxidation (Oppenauer oxidation) to obtain 7-Dehydro-9beta, 10 alpha-progesterone, and finally, carrying out olefin shift isomerization under the action of acid to obtain the final product 6-Dehydro-9beta, 10 alpha-progesterone (a crude drug of dydrogesterone). The method is economical in steps and comprises four conversion steps; the total yield is as high as 16.4%; the raw materials are cheap and easy to obtain, the whole process route is green and safe, the bulk drugs are high in quality, the purity can reach 99.5% or above, and the method is suitable for industrial production.

Discovery of novel 3-hydroxyandrosta-5,7-Diene-17-Carboxylic acid derivatives as anti-inflammatory bowel diseases (IBD) agents

A series of steroidal compounds based on 3-hydroxyandrosta-5,7-diene-17-carboxylic acid core structure were designed, synthesized and bio-evaluated for their anti-inflammatory potency. Among them, compound 5c, 6f, and 6q effectively inhibited the producti

Biogenesis-Guided Synthesis and Structural Revision of Sarocladione Enabled by Ruthenium-Catalyzed Endoperoxide Fragmentation

Sarocladione is the first 5,10:8,9-diseco-steroid with a 14-membered macrocyclic diketone framework to have been isolated from a natural source. Herein we report a biomimetic synthesis of sarocladione in only two or seven steps from inexpensive, commercially available ergosterol. The key feature of this synthesis was a novel ruthenium-catalyzed endoperoxide fragmentation, which transformed various saturated endoperoxides into olefinic diketones by cleavage of two C?C bonds. This synthesis allowed us to unambiguously determine the structure of sarocladione and provided experimental support for its revised biosynthetic origin. This work also vividly demonstrates that consideration of the biogenesis is a powerful tool for elucidating the structures of natural products.

Chemical synthesis of 20S-hydroxyvitamin D3, which shows antiproliferative activity

20S-hydroxyvitamin D3 (20S-(OH)D3), an in vitro product of vitamin D3 metabolism by the cytochrome P450scc, was recently isolated, identified and shown to possess antiproliferative activity without inducing hypercalcemia. The enzymatic production of 20S-(OH)D3 is tedious, expensive, and cannot meet the requirements for extensive chemical and biological studies. Here we report for the first time the chemical synthesis of 20S-(OH)D3 which exhibited biological properties characteristic of the P450scc-generated compound. Specifically, it was hydroxylated to 20,23-dihydroxyvitamin D3 and 17,20-dihydroxyvitamin D3 by P450scc and was converted to 1α,20-dihydroxyvitamin D3 by CYP27B1. It inhibited proliferation of human epidermal keratinocytes with lower potency than 1α,25-dihydroxyvitamin D3 (1,25(OH)2D3) in normal epidermal human keratinocytes, but with equal potency in immortalized HaCaT keratinocytes. It also stimulated VDR gene expression with similar potency to 1,25(OH)2D3, and stimulated involucrin (a marker of differentiation) and CYP24 gene expression, showing a lower potency for the latter gene than 1,25(OH)2D3. Testing performed with hamster melanoma cells demonstrated a dose-dependent inhibition of cell proliferation and colony forming capabilities similar or more pronounced than those of 1,25(OH)2D3. Thus, we have developed a chemical method for the synthesis of 20S-(OH)D3, which will allow the preparation of a series of 20S-(OH)D3 analogs to study structure-activity relationships to further optimize this class of compound for therapeutic use.

Efficient Process for Preparing Steroids and Vitamin D Derivatives With the Unnatural Configuration at C20 (20 Alpha-Methyl) from Pregnenolone

Disclosed herein are methods for preparing steroids and Vitamin D derivatives having the unnatural beta (usually S) configuration at C20, the methods comprising the use of compounds of the formula: wherein R is as defined herein. Also disclosed are steroids and Vitamin D derivatives made using the methods disclosed herein and pharmaceutical compositions comprising said steroids and Vitamin D derivatives.

Inhibition of Ecdysone Biosynthesis: Preparation of Acetylenic Intermediates

Key Words: Ecdysone; C-22 Hydroxylase; Ecdysteroid inhibitor; Acetylenic inhibitor; Hydroboration. Several acetylenic derivatives of ecdysone were synthesized from pregnenolone.These compounds carry an acetylenic function at C-22 and were devised with the aim to inhibit the C-22 hydroxylation of ecdysone biosynthesis by a suicide-substrate mechanism.The five compounds synthesized inhibit the synthesis of ecdysone in the prothoracic glands of Locusta migratoria in vitro.

Studies on vitamin D (Calciferol)and its analogues. 10. Side chain analogues of 25 hydroxyvitamin D3

A homologous series of side chain analogues of 25 hydroxyvitamin D3 (25 hydroxycholecalciferol) in which the length of the side chain is modified while maintaining its characteristic tertiary hydroxyl moiety has been synthesized. The following five analogues have been prepared and characterized: pentanor 25 OH D3 (2a), trinor 25 OH D3 (2b), dinor 25 OH D3 (2c), nor 25 OH D3 (2d), and homo 25 OH D3 (2e). Biological assays in vivo of intestinal calcium absorption and bone calcium mobilization in the chick of the five analogues revealed that the homo analogue 2e exhibited a significant biological response relative to the -D (-vitamin D3) control. Compared to the natural vitamin D3, 2e is as active in its ability to mobilize bone calcium and is about half as effective in stimulating intestinal calcium transport. The remaining analogues (2a d) exhibited no significant activity in either assay, although the nor analogue 2d was previously observed to exhibit antimetabolite activity.