1670-49-1

Usage

Classification

Synthetic compound belonging to the class of anabolic-androgenic steroids (AAS)

Derivation

Derived from nandrolone, a naturally occurring hormone in the human body

Main Properties

1. Anabolic Effects: Known for its strong anabolic effects
2. Popularity: Popular among bodybuilders and athletes for enhancing muscle growth and physical performance
3. Legal Status: Banned in competitive sports due to its potential for abuse and adverse health effects

Form of Availability

Sold as a dietary supplement or performance-enhancing drug

Risk Awareness

Important to be aware of potential risks and legal implications before use

Upstream product

• 1624-62-0 estrone 3-methyl ether 
• 59975-02-9 9α-Hydroxy-3-methoxy-1,3,5(10)-oestratrien-17-on 
• 90243-01-9 2-(formylmethyl)-3-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-2-methylcyclopentanone 
• 968-98-9 3-methoxy-9,10-secoestra-1,3,5⁽¹⁰⁾-triene-9,17-dione 
• 91413-54-6 10β-Chlor-3,3-dimethoxy-oestra-1,4-dien-17-on 
• 1089-80-1 3-hydroxy-estra-1,3,5⁽¹⁰⁾,9⁽¹¹⁾-tetraen-17-one 
• 77-78-1 dimethyl sulfate 
• 6885-44-5 (+)-3-methoxy-1,3,5⁽¹⁰⁾,8-estratetraen-17-one 
• 75863-24-0 (1ω,5S)-1-Methyl-2-oxo-5-vinyl-1,3-cyclopentandicarbonsaeure-dimethylester 
• 116139-11-8 1,2-Dihydro-4,7-dimethoxynaphthalene 
• 126723-83-9 (Z)-(S)-8,9-Dihydroxy-7-methyl-non-6-en-2-ynoic acid methyl ester 
• 126696-27-3 (Z)-7-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-oct-6-en-2-ynoic acid methyl ester 
• 83747-51-7 [(1S,2S)-2-(6-Methoxy-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-1-methyl-5-oxo-cyclopentyl]-acetaldehyde 
• 900-83-4 (8R,9S,13S,14S)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2′-[1,3]dioxolan]-3-ol 

Downstream Products

• 1624-62-0 estrone 3-methyl ether 
• 28336-29-0 17,17-ethylenedioxy-3-methoxyoestra-1,3,5⁽¹⁰⁾-triene 
• 53-16-7 Estrone 
• 1091-94-7 (+/-)-oestrone methyl ester 
• 966-46-1 rac-3-Methoxy-1,3,5⁽¹⁰⁾,9⁽¹¹⁾-oestratetraen-17-on 
• 2911-86-6 (+/-)-3-methoxyestra-1,3,5⁽¹⁰⁾,8-tetraen-17-one 
• 966-47-2 3-methoxy-estra-1,3,5⁽¹⁰⁾,8⁽⁹⁾,14⁽¹⁵⁾-pentaene-17-one 
• 3907-67-3 3-O-methylequilinine 

Relevant academic research and scientific papers

Regio- and stereoselective azidation of 19 norsteroids

The proton at C-9 of 3-methoxyestra-1,3,5(10)-trienes 1-4 was replaced by an azido group regio- and stereospecifically in one step by reaction with hydrazoic acid in chloroform in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).

A [4+1] cyclopentannulation route to ring A aromatic, C(1)-C(11) methano-bridged steroids

In a novel, one-pot [4+1] cyclopentannulation procedure, the steroidal olefin 2 and CH2O are converted into the corresponding C(1)-C(11) methano-bridged derivative 3 by two sequential Lewis acid-promoted electrophilic substitutions. Birch reduction of the olefin 3, followed by removal of the protecting groups, affords 1,11α-methano-9β-estra-1,3,5(10)-triene-3,17β-diol (6).

A short, scalable synthesis of the carbocyclic core of the anti-angiogenic cortistatins from (+)-estrone by B-ring expansion

(Chemical Equation Presented) A rapid and scalable synthesis of the carbocyclic core of the potent antiangiogenic natural products, the cortistatins, is presented starting from readily available (+)-estrone. Key steps include a regio- and stereoselective benzylic cyanation and a Demjanov rearrangement.

Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates

Herein we describe a general, mild, and scalable method for hydrodeoxygenation of readily accessible tertiary alkyl oxalates by Zn/silane under Ni-catalyzed conditions. The reduction method is suitable for an array of structural motifs derived from tertiary alcohols that bear diverse functional groups, including the synthesis of a key intermediate en route to estrone.

Design, synthesis, and biological evaluation of steroidal analogs as estrogenic/anti-estrogenic agents

Series of estrone based analogs were synthetically investigated at positions C-9, C-11, C-16, and C-17 positions, to be biologically evaluated via assessment of cell proliferation, cytotoxicity, and estrogenic/anti-estrogenic activity. LA-7 and LA-10 revealed their potential to exhibit inhibitory estrogenic profile. This was further validated by Estrogen Receptor-α (ER-α) and Estrogen Receptor-β (ER-β) competitive binding assays to reveal the high selective affinity of LA-7 towards ER-α at 5.49 μM, while LA-10 did not show any binding affinity towards neither ER-α nor ER-β; suggesting another mechanism for inhibition. This was validated by in silico molecular docking simulations of LA-7 to reveal the optimum binding affinity of LA-7 towards ER-α.

CORTISTATIN ANALOGUES AND SYNTHESES AND USES THEREOF

Provided herein are compounds of Formula (A), (B), (C), (D) and (E), pharmaceutically acceptable salts, quaternary amine salts, and N-oxides thereof, and pharmaceutical compositions thereof. Compounds of Formula (A), (B), (C), (D), and (E) are contemplated useful as therapeutics for treating a wide variety of conditions, e.g., including but not limited to, conditions associated with angiogenesis and with CDK8 and/or CDK19 kinase activity. Further provided are methods of inhibiting CDK8 and/or CDK19 kinase activity, methods of modulating the β-catenin pathway, methods of modulating STAT1 activity, methods of modulating the TGFβ/BMP pathway, methods of modulating HIF-1 -alpha activity in a cell, and methods of increasing BIM expression to induce apoptosis, using a compound of Formula (A), (B), (C), (D), or (E). Further provided are CDK8 and CDK19 point mutants and methods of use thereof.

A new route to (+)-estrone using a bicyclo[3.2.1]octane chiral building block.

A new route to (+)-estrone has been developed starting from the chiral building block having a bicyclo[3.2.1]octane framework based on the inherent stereochemical chemical nature of the chiral building block.

Synthese stereoselective de 12α-amino et 12α-aminomethyl 19-nor-steroides

Stereoselective synthesis of 12α-amino and 12α-aminomethyl 19-nor-steroids.The regio- and stereoselective introduction of an azido or a cyano group in the 12α-position of aromatic steroids was achieved by oxidative nucleophilic substitution (SNOx).A combination of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) as an oxidant and cyano(trimethyl)silane (TMSCN) or azido(trimethyl)silane (TMSA) as a nucleophile thus led to the smooth functionalization of the 12α-position with high yields and selectivity.The method involves a two-step procedure : Δ 9-11 formation by dehydrogenation with DDQ/MeOH followed by oxidative nucleophilic substitution with DDQ in the presence of TMSA or TMSCN/LiClO4.During the second step, the carbocation generated in the medium is selectively attacked on the α face and leads to the more thermodynamically stable 12α-compounds, which were readily converted into the corresponding amino estrogens upon treatment with a variety of reducing reagents. Key words: regioselectivity / stereoselectivity / steroids / 2,3-dichloro-5,6-dicyanobenzoquinone

Total synthesis with a chirogenic opening move demonstrated on steroids with estrane or 18a-homoestrane skeleton

A concept of first choice for the synthesis of the title compounds had been proposed by Dane in the late 1930s. It was soon turned down, because the opening move - a chirogenic Diels-Alder reaction - did not work. With Lewis acids as mediators, however, a successful start has been achieved now. With Ti complexes of chelating ligands (Seebach's TADDOLs (= α,α,α',α'-tetraaryl-1,3-dioxolane-4,5-dimethanols)), enantioselective formation of the desired adducts does occur. Efficient total syntheses of 2 and 3a have been accomplished.

Asymmetric tandem Claisen-ene strategy for convergent synthesis of (+)-9(11)-dehydroestrone methyl ether: Stereochemical studies on the ene cyclization and cyclic enol ether Claisen rearrangement for steroid total synthesis

An asymmetric synthesis of (+)-9(11)-dehydroestrone methyl ether (1), a key intermediate for estrogen analogs, is described using a new strategy of consecutive carbocyclizations for the D and C rings of the steroid skeleton based on an asymmetric tandem C