2590-41-2

Basic information

• Product Name: Dehydronandrolon
• Synonyms: 4,6-ESTRADIEN-17-BETA-OL-3-ONE ACETATE;6-DEHYDRONANDROLONE ACETATE;17-ACETOXYESTRA-4,6-DIEN-3-ONE;17b-Acetyloxy-estra-4,6-diene-3-one;DEHYDRONANDROLON;(8R,9S,13S,14S,17S)-13-Methyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate;Dehydronandrolone Acetate;Dehydronandrolone-6 Acetate
• CAS NO: 2590-41-2
• Molecular Formula: C₂₀H₂₆O₃
• Molecular Weight: 314.42
• EINECS: 1308068-626-2
• Product Categories: Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;API
• Mol File: 2590-41-2.mol

Chemical Properties

• Melting Point: 95-98?C
• Boiling Point: 457.4 °C at 760 mmHg
• Flash Point: 200.6 °C
• Appearance: /
• Density: 1.15 g/cm³
• Refractive Index: 1.559
• Storage Temp.: Controlled Substance, -20?C Freezer
• CAS DataBase Reference: Dehydronandrolon(CAS DataBase Reference)
• NIST Chemistry Reference: Dehydronandrolon(2590-41-2)
• EPA Substance Registry System: Dehydronandrolon(2590-41-2)

Safety Data

• Hazardous Substances Data: 2590-41-2(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

Tibolone intermediate.

InChI:InChI=1/C20H26O3/c1-12(21)23-19-8-7-18-17-5-3-13-11-14(22)4-6-15(13)16(17)9-10-20(18,19)2/h3,5,11,15-19H,4,6-10H2,1-2H3/t15?,16?,17?,18?,19?,20-/m0/s1

Upstream product

• 14531-84-1 17β-hydroxyestra-4,6-dien-3-one 
• 108-24-7 acetic anhydride 
• 70286-48-5 3-acetoxy-19-nor-androsta-3,5-dien-17-one 
• 734-32-7 estra-4-ene-3,17-dione 
• 1164-99-4 17β-acetoxy-4-chloro-estr-4-en-3-one 
• 4999-76-2 3,17β-diacetoxyoestra-3,5-diene 
• 1425-10-1 19-nortestosterone acetate 
• 434-22-0 19-nortestosterone 
• 6925-84-4 3-Ethoxy-17β-acetoxy-19-nor-androsta-3,5-dien 

Downstream Products

• 6157-87-5 7alpha-Methyl-19-nortestosterone acetate 
• 875573-69-6 17-O-acetyl-S-deoxo-fulvestrant 
• 129453-61-8 fulvestrant 
• 153004-31-0 (+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol 
• 875573-66-3 (+)-(7α)-[9-bromononyl]estra-1,3,5(10)-triene-3-ol-17β-yl acetate 
• 875573-63-0 (+)-3-oxo-(7α)-[9-bromononyl]estr-4-en-17β-ylacetate 
• 415927-29-6 3-oxo-7α-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-4-en-17βyl acetate 
• 1239977-74-2 3-oxo-7β-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-4-en-17βyl acetate 
• 54793-00-9 17β-hydroxy-7α-methyl-estr-5-en-3-one acetate 
• 13209-45-5 estra-4,6-diene-3,17-dione 
• 474-86-2 equilin 
• 115759-24-5 (3S)-3,17β-bis-(3,5-dinitro-benzoyloxy)-9,10-seco-estra-5(10),6t,8-triene 
• 98008-50-5 11-(17β-acetoxy-3-benzoyloxyestra-1,3,5(10)-trien-7α-yl)undecanoic acid 
• 125151-25-9 17β-Acetoxy-3-benzoyloxy-7α-(11-hydroxyundecyl)estra-1,3,5(10)-triene 

Relevant articles and documents

Optimization of copper(I)-catalyzed 1,6-conjugate addition of a methyl group to 17β-acetoxy-4,6-estradien-3-one

7α-Methyl-19-nortestosterone (1) was synthesized from 19-nortestosterone (2) via 17β-acetoxy-4,6-estradien-3-one (4). The critical parameters for the synthesis of compound (1) have been identified. An optimization procedure consisting of an iterative, two-stage reaction response surface analysis was carried out. As a result, the synthesis of the target compound (1) from the intermediate (4) was achieved under the newly determined conditions, in a repeatable manner. This afforded compound (1) in an yield of over 60%, essentially free from the 7β-Me isomer (6), under experimental conditions amenable for scale enhancement.

Preparation method of 6-dehydronandrolone acetate

The invention belongs to the technical field of steroid drug intermediates, and provides a preparation method of 6-dehydronandrolone acetate. The preparation method comprises the following steps: carrying out a catalytic reaction on estra-4-ene-3,17-dione, acetic anhydride and p-toluenesulfonic acid to obtain a compound 1; carrying out a reduction reaction on the compound 1, hydroboron and aluminum trichloride to obtain a compound 2; subjecting the compound 2 and N-bromosuccinimide to reacting with DMF to obtain a solution of a compound 3; carrying out an addition reaction on the solution of the compound 3 and alkali to obtain a compound 4; and subjecting the compound 4, acetic anhydride, triethylamine and dichloromethane to a catalytic reaction to obtain 6-dehydronandrolone acetate. By adding borohydride and the aluminum trichloride in a reasonable ratio, hydrolysis of a 3-site ester group is effectively avoided, and side reactions are few; and meanwhile, the yield and the purity of a target product are remarkably improved by reasonably setting a synthesis route and controlling a reaction temperature.

METHODS OF TREATING ADVANCED PROSTATE CANCER

Provided herein are methods for treating metastatic prostate cancer using anti-androgen compounds and radionuclide-labeled androgens.

Preparation method of 6-dehydronandrolone

The invention relates to a preparation method of 6-dehydronandrolone. The preparation method comprises the following steps: putting a No. 8 magneton into a three-necked flask, dissolving a compound, namely, 3,5-estradiene-3,17beta-ester diacetate in a DMF (Dimethyl Formamide) water mixed solution for reacting to obtain a mixed solution I, dissolving DMF in an NBS (N-bromosuccinimide) solution to obtain a mixed solution II, adding the mixed solution II into the mixed solution I dropwise for reacting, adding sodium carbonate into a reaction system firstly, adding sodium bromide after full reaction, heating to 40 DEG C, gradually heating to 80 DEG C, and continually reacting for 3 hours till the reaction ends; cooling, adding an acetic acid aqueous solution for reacting with stirring, adding an equivalent acetic acid aqueous solution, and continually stirring overnight; precipitating a solid, filtering a product, cleaning a filter cake with a cold isopropanol aqueous solution, and drying to obtain pure 6-dehydronandrolone. The preparation method is simple and convenient, is easy to operate, and is up to 80 percent in yield; the synthesized 6-dehydronandrolone as a steroid drug is one of important prodrugs of tibolone.

PROCESS AND INTERMEDIADES FOR THE PREPARATION OF 7-ALKYLATED STEROIDS

A process for preparing compounds of formula (I), or a salt, solvate or stereoisomer thereof, including Fulvestrant, which process comprises free radical to a compound of formula (III), or a salt, solvate or stereoisomer thereof. The invention also refers to intermediates of said process.

Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803

A series of 3-, 7-, 15-, and 16-methyl-substituted steroid analogs were synthesized via a highly stereoselective 1,6-conjugate addition. Under the catalysis of CuBr, AlMe3 reacted with four steroid dienone precursors to afford either the corresponding α-epimer of C-3 and C-7 methyl-substituted steroids as the major products, and the ratio of α/β was up to 10/1. No β-epimer has been detected for methyl addition at C-16. However, under the same reaction conditions, enantioselective methyl addition at C-15 afforded the 15β-epimer as the major product. The preliminary SAR analysis showed that the methyl substituents at C-7α and C-15β positions lead to a dramatical increase in potency against human gastric cancer cell line MGC-803.

PROCESS FOR THE PRODUCTION OF TIBOLONE

Disclosed is a process for the synthesis of 17β-hydroxy-7α-methyl- 19-nor-17α-pregn-5(10)-ene-20-yne-3-one (tibolone, 11) and intermediates useful for the synthesis thereof: (11).

Anti-estrogenic compounds and compositions

Inhibitors of sex steroid activity, for example those having the general structure STR1 may be used as part of a pharmaceutical composition to provide antiestrogenic effects and/or to suppress estrogen synthesis. Such pharmaceutical compositions are useful for the treatment of breast cancer or other diseases whose progress is aided by activation of sex steroid receptors.

Estrogen nucleus derivatives for use in inhibition of sex steroid activity

Novel compounds for the inhibition of sex steroid activity for the treatment of both androgen-related and estrogen-related diseases include for example 15- and 16-halo substituted compounds such as: STR1 The compounds are characterized by an estrogenic nucleus substituted with a substituent of the formula --R1 [B--R2 --]x L--G wherein at least one of L and G is a polar moiety distanced from a ring carbon of the estrogenic nucleus by a least three intervening atoms: x is an integer from 0-6; R1 and R2 are independently either absent or selected from the group consisting of straight- or branched-chain alkylene, straight- or branched-chain alkynylene, straight- or branched-chain alkenylene, phenylene, and fluoro-substituted analogs of the foregoing; and B is either absent or selected from the group consisting of --O--, --Se--, --SO--, --SO2 --, --NR3 --, --SiR32, --CR3 OR3 --, NR3 CO--, NR3 CS--, --CONR3 --, CSNR3 --, --COO--, --COS--, --SCO--, --CSS--, --SCS--, --OCO-- and phenylene (R3 being hydrogen or lower alkyl).

The Preparation of 7α- and 7β-Allyloestradiol, and an Unusual Titanium(IV) Chloride Mediated Dimerisation

17β-Acetoxyoestra-4,6-dien-3-one reacts with allyltrimethylsilane in the presence of fluoride ion to give the 7α- and 7β-allyloestr-4-en-3-ones in low yield.With titanium(IV) chloride catalysis, the 7α-allyloestr-4-en-3-one is the only product at -78 deg C, but its novel 6β,6'β-'dimer' is also formed at higher temperatures.The isomeric 7-allyloestr-4-en-3-ones have been aromatised to give 7α- and 7β-allyloestradiols.