2099-26-5

Usage

Uses

Used in Performance Enhancement:
Androstenediol diacetate is used as a performance-enhancing drug for its ability to promote muscle growth, increase strength, and endurance, as well as enhance athletic performance. However, it is important to note that its use is banned by many sports organizations due to its potential for abuse and health risks.
Used in Pharmaceutical Industry:
Androstenediol diacetate is used as an intermediate in the synthesis of other steroids for various pharmaceutical applications. Its role in the production of sex hormones makes it valuable in the development of medications for hormone-related conditions.
Used in Therapeutic Applications:
Androstenediol diacetate is studied for its potential therapeutic applications in conditions such as osteoporosis, where it may help improve bone density, and hormone replacement therapy, where it can serve as a precursor for the production of essential hormones.

Upstream product

• 93-59-4 Perbenzoic acid 
• 1778-02-5 Pregnenolone acetate 
• 25256-95-5 3β,17β-Diacetoxy-androsta-5,16-diene 
• 4350-67-8 17β-acetamidoandrost-5-en-3β-ol acetate 
• 1259-22-9 5-androstene-3β,17β-diol 3-acetate 17-p-toluene-δ-sulfonate 
• 108-24-7 acetic anhydride 
• 1639-43-6 androstenediol-3-acetate 
• 1159-66-6 3β,17β-dihydroxyandrost-5-en-16-one 
• 53-43-0 dehydroepiandrosterone 
• 4968-05-2 androstane-3,5-dien-17-one-3β-ol acetate 
• 63-05-8 Androstenedione 
• 521-17-5 5-androstenediol 
• 13209-60-4 3β, 17β-diacetoxyandrost-5-ene-7-one 
• 15426-21-8 5α-Fluor-3β,17β-dihydroxy-6-nitrimino-androstan-diacetat 

Downstream Products

• 156896-66-1 Acetic acid (1S,3aS,4S,5S,7aS)-4-(2,2-dimethoxy-ethyl)-7a-methyl-5-((R)-1-methyl-2-oxo-cyclohex-3-enyl)-octahydro-inden-1-yl ester 
• 7745-18-8 5-bromo-6β,19-epoxy-5α-androstane-3β,17β-diol 
• 6171-48-8 4-Methyl-oestradiol 
• 3404-23-7 3β,17β,19-trihydroxyandrost-5-ene 
• 13209-60-4 3β, 17β-diacetoxyandrost-5-ene-7-one 
• 140421-65-4 3β-hydroxy-16E-oximinoandrost-5-en-17-one 
• 2243-06-3 androst-4-ene-3,6,17-trione 
• 2697-85-0 5-androstene-3β,7β,17β-triol 
• 116280-94-5 3β,17β-bis-benzoyloxy-5α-androst-7-ene 
• 16759-13-0 3β,17β-Diacetoxy-5α-androst-7-en 
• 13209-61-5 3β,17β-Diacetoxy-7-oxo-5α-androstan 
• 28375-34-0 3β,17β-dihydroxy-5α-androstanone-(7) 
• 6911-95-1 Testosteron-oxim 
• 1045-69-8 testosterone acetate 

Relevant academic research and scientific papers

Sensitized Aliphatic Fluorination Directed by Terpenoidal Enones: A "visible Light" Approach

In our continued effort to address the challenges of selective sp3 C-H fluorination on complex molecules, we report a sensitized aliphatic fluorination directed by terpenoidal enones using catalytic benzil and visible light (white LEDs). This sensitized approach is mild, simple to set up, and an economical alternative to our previous protocol based on direct excitation using UV light in a specialized apparatus. Additionally, the amenability of this protocol to photochemical flow conditions and preliminary evidence for electron-transfer processes are highlighted.

Multiple Enone-Directed Reactivity Modes Lead to the Selective Photochemical Fluorination of Polycyclic Terpenoid Derivatives

In the realm of aliphatic fluorination, the problem of reactivity has been very successfully addressed in recent years. In contrast, the associated problem of selectivity, that is, directing fluorination to specific sites in complex molecules, remains a great, fundamental challenge. In this report, we show that the enone functional group, upon photoexcitation, provides a solution. Based solely on orientation of the oxygen atom, site-selective photochemical fluorination is achieved on steroids and bioactive polycycles with up to 65 different sp3 C-H bonds. We have also found that γ-, β-, homoallylic, and allylic fluorination are all possible and predictable through the theoretical modes reported herein. Lastly, we present a preliminary mechanistic hypothesis characterized by intramolecular hydrogen atom transfer, radical fluorination, and ultimate restoration of the enone. In all, these results provide a leap forward in the design of selective fluorination of complex substrates that should be relevant to drug discovery, where fluorine plays a prominent role.

5 α-chloro-androl -6β, 19-epoxy -3,17-dione method for the preparation of

The invention provides a method for preparing 5 alpha-chlorine-androstane-6 beta, 19-epoxy-3,17-diketone. The method comprises the following steps: taking 4-AD as a raw material, carrying out 3-position enol esterification, reduction, 3,17-position double esterification, 5,6-position addition, 6,19-cyclization and 3,17-position double oxidation, and finally obtaining 5 alpha-chlorine-androstane-6 beta, 19-epoxy-3,17-diketone. The method has the advantages of being rich in raw material sources, environmentally-friendly, low in cost and high in yield of synthetic process, and the obtained 5 alpha-chlorine-androstane-6 beta, 19-epoxy-3,17-diketone can be applied to producing series of family planning drugs.

Synthesis and antiproliferative activity of some androstene oximes and their O-Alkylated derivatives

In order to study the structure-activity relationship with respect to the cytotoxicity of steroidal oximes, several 6E-hydroximino-4-ene steroids and their O-alkylated derivatives were synthesized. The oxime ethers were solidified and purified by preparing their corresponding oxalate salts. The new derivatives as well as some previously synthesized ones were evaluated for in vitro antineoplastic activity against a panel of 60 cancer cell lines at 10 μM. The oximes and oxime ethers were found to have moderate to good antiproliferative activity against various leukemia, colon, melanoma, and renal cancer cell lines. Several 6E-hydroximino-4-ene steroids and their O-alkylated derivatives were synthesized. Their structure-activity relationship with respect to the cytotoxicity of steroidal oximes was studied. The oximes and oxime ethers were found to have moderate-to-good antiproliferative activity against various leukemia, colon, melanoma, and renal cancer cell lines.

NOVEL SERIES OF IMIDAZOLYL SUBSTITUTED STEROIDAL AND INDAN-1-ONE DERIVATIVES

The present invention provides a novel series of imidazolyl substituted steroidal and indan-1-one derivatives and salts thereof having the following general structural formulae (A and B)

Synthesis and antineoplastic activity of O-alkylated derivatives of 7-hydroximinoandrost-5-ene steroids

Varied positioning of the hydroximino group on the parental steroid skeleton results in remarkable changes in the antineoplastic activity profile of the compounds. Here, the compound 7-oximino-5-androstene and its O-alkylated derivatives have been prepared and screened for cytotoxic and aromatase inhibitory activity. The steroidal 7-oximino ether derivatives exhibited insignificant cytotoxic effects when screened against three cancer cell lines, MCF-7 (breast), NCl-H460 (lung), and SF-268 (CNS) at 100 μM. However, the imidazolyl-substituted steroidal oxime ethers displayed moderate inhibition of cytochrome P450 aromatase.

NOVEL SERIES OF IMIDAZOLYL SUBSTITUTED STEROIDAL AND INDAN-1-ONE DERIVATIVES

The present invention provides a novel series of imidazolyl substituted steroidal and indan-1-one derivatives and salts thereof having the following general structural formulae (A and B)

Zinc(II) iodide-triethylsilane: A novel mild reduction system for direct deoxygenation of aryl aldehydes, ketones, and α,β-unsaturated enones

ZnI2-TESH has been found to be a novel mild and efficient reduction system. This reagent, in contrast to the traditional ionic deoxygenation systems (TFA-R3SiH, BF3·OEt 2-R3SiH, etc.), could directly deoxygenate different kinds of carbonyl compounds such as aryl aldehydes, ketones, and αβ- unsaturated enones to the corresponding hydrocarbons in moderate to excellent yields. Georg Thieme Verlag Stuttgart.

Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide

Dibutyltin oxide (DBTO) was first utilized for the deacetylation of steroid and diterpene esters. The results showed the deprotection of acetylated steroids and diterpenes separately with moderate catalysis dibutyltin oxide in methanol selectively removed part acetyl groups of these substrates, whereas several functional groups of the steroids and diterpenes were retained and neither isomerization nor degradation of these substrates was observed. It seems that the acetyl groups with lower steric hindrance or near carbonyl, alkoxy, or hydroxyl groups can be cleaved by the reaction, whereas the acetyl groups with higher steric hindrance or without carbonyl, alkoxy, or hydroxyl groups neighboring were retained under the same conditions. One of the interesting results obtained was the selective hydrolysis of the 3β-O-acetyl group in the presence of the 6β group in 3β,6β-Di-O-acetyl-5α-hydroxypregn-16-en-20-one. This allows for subsequent introduction of one unit at C-3 and the other unit at C-6. This procedure is useful for the synthesis of a series of closely related isomers of 3β,5α,6β-trihydroxypregn-16-en-20-one and other widespread polyhydroxysteroids in marine organisms and some terrestrial species.

Structure-activity relationship study of androstene steroids with respect to local anti-inflammatory activity

A sex hormone, 37β-acetoxy-17β-hydroxy-androst-5-ene (1) (CAS 1639-43-6), was isolated from aerial parts of Acacia nilotica. This compound is reported to have anti-inflammatory activity. In view of this, considering this molecule as a lead molecule different androstene compounds were synthesized to study their potency and structure-activity relationship with respect to local anti-inflammatory activity. The experiments indicated that 17 ketonic compounds were more active towards inflammation than their oxime analogues. Similarly, for the compounds containing an acetyl group fixed at C-3 position a decreasing trend of activity was observed in the order of ketonic, hydroxyl, oxime and acetyl group, respectively, when these groups are at C-17 position. ECV · Editio Cantor Verlag, Aulendorf.