13209-60-4

Usage

InChI:InChI=1/C23H32O5/c1-13(24)27-16-7-9-22(3)15(11-16)12-19(26)21-17-5-6-20(28-14(2)25)23(17,4)10-8-18(21)22/h12,16-18,20-21H,5-11H2,1-4H3

Upstream product

• 13209-61-5 3β,17β-Diacetoxy-7-oxo-5α-androstan 
• 853-23-6 prasterone acetate 
• 53-43-0 dehydroepiandrosterone 
• 108-24-7 acetic anhydride 
• 2099-26-5 androstenediol-3,17-diacetate 
• 64-19-7 acetic acid 
• 1333-82-0 chromium(VI) oxide 
• 521-17-5 5-androstenediol 
• 66917-28-0 Acetic acid (3S,5S,6R,7R,8S,9S,10R,13S,14S,17S)-17-acetoxy-7-hydroxy-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[5,6]cyclopenta[a]phenanthren-3-yl ester 
• 1449-61-2 3-O-acetyl-7-oxo-dehydroepiandrosterone 

Downstream Products

• 28375-34-0 3β,17β-dihydroxy-5α-androstanone-(7) 
• 13209-61-5 3β,17β-Diacetoxy-7-oxo-5α-androstan 
• 2697-85-0 5-androstene-3β,7β,17β-triol 
• 137196-49-7 7-phenylandrost-5-ene-3β,7ξ,17β-triol 
• 16759-13-0 3β,17β-Diacetoxy-5α-androst-7-en 
• 116280-94-5 3β,17β-bis-benzoyloxy-5α-androst-7-ene 
• 2697-85-0 Androst-5-ene-3beta,7alpha,17beta-triol 
• 2099-26-5 androstenediol-3,17-diacetate 
• 137196-59-9 7α-(4-(2-pyrrolidinoethoxy)phenyl)androst-5-ene-3β,7β,17β-triol 
• 137196-58-8 7α-(4-(2-N,N-diethylaminoethoxy)phenyl)androst-5-ene-3β,7β,17β-triol 
• 137196-57-7 7α-(4-hydroxyphenyl)androst-5-ene-3β,7β,17β-triol 
• 14946-72-6 7β-hydroxy-3β.17β-diacetoxy-10.13-dimethyl-5α-gonane 
• 137255-20-0 7α-(4-N,N-dimethylaminophenyl)androst-5-ene-3β,7β,17β-triol 
• 137196-52-2 7α-(4-benzyloxyphenyl)androst-5-ene-7β,17β-diol-3β-yl acetate 

Relevant academic research and scientific papers

Synthesis of 19-hydroxy-androstenedione for human metabolism studies

19-Hydroxyandrostenedione (19-OHA), highly labeled with deuterium at position 7, was synthesized from unlabeled androstenediol diacetate.The deuterium labels were introduced into the 7-keto compound with dichloroaluminum deuteride to obtain androstenediol.The labeled androstenediol diacetate was converted to the labeled 19-OHA by a five-step sequence without appreciable loss of deuterium.The labeled 19-OHA is useful as an internal standard for gas chromatography-mass spectroscopy analysis of the endogenous levels and as a tracer for in vivo metabolic studies.

Novel stereoselective synthesis of 7β-methyl-substituted 5-androstene derivatives

The 7β-methyl-5-androstene derivatives 11a-c were prepared in good yield with high stereoselectivities starting from 3β-acetoxyandrost-5-en-17-one 4. The addition of methylmagnesium iodide to the 7-carbonyl group of 7a-c gave, after hydrolysis, two isomers 9a-c and 10a-c, which were stereoselectively deoxygenated by means of an ionic hydrogenation to afford the compounds 11a-c.

Identification and quantification of dehydroepiandrosterone sulphate in saliva

3β-Hydroxy-5-androsten-17-one (dehydroepiandrosterone) sulphate has been separated from an extract of human saliva by ion exchange gel chromatography and identified by high resolution gas chromatography-high resolution mass spectrometry of the tert-butyldimethylsilyl derivative of the neutral steroid obtained by enzymic hydrolysis. Quantitative analyses, employing 7,7-2H-dehydroepiandrosterone sulphate as the internal standard, have indicated concentrations in the saliva of young adult subjects to be generally in the range 0.9-5.7 nmol/l, though concentrations as high as 10.7 nmol/l have been observed.

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.

Cooperative Noncovalent Interactions Lead to a Highly Diastereoselective Sulfonyl-Directed Fluorination of Steroidal α,β-Unsaturated Hydrazones

A series of steroidal α,β-unsaturated hydrazones is presented whose behavior and reactivity are governed by various types of weak C-H hydrogen bonds. Several interesting features in a representative X-ray crystal structure and 1H NMR spectrum are examined that provide evidence for a unique bifurcated intramolecular C-H interaction. Moreover, these steroid derivatives undergo functionalization in the form of a highly regio- and stereoselective fluorination; the sulfonyl oxygen atoms are proposed to direct the fluorinating reagent through C-H hydrogen bonds.

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.

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)

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)

Mild manganese(III) acetate catalyzed allylic oxidation: Application to simple and complex alkenes

Manganese(III) acetate catalyzed allylic oxidation of alkenes to the corresponding enones was investigated, showing excellent regioselectivity and chemoselectivity (functional group compatibility). Δ5-Steroids were transformed into bioactive Δ5-en-7-ones under a nitrogen atmosphere, whereas simple alkenes were converted into the corresponding enones under an oxygen atmosphere in good yields.