4682-70-6

Usage

Uses

Used in Biological Research:
19-Nordeoxycorticosterone is used as a research compound for studying the relationship between the structure of pregnanesteroids, their affinity for renal mineralocorticoid receptors, and their anti-natriuretic effects. This helps in understanding the mechanisms of action and potential applications in various physiological and pathological conditions.

InChI:InChI=1/C20H28O3/c1-20-9-8-15-14-5-3-13(22)10-12(14)2-4-16(15)17(20)6-7-18(20)19(23)11-21/h10,14-18,21H,2-9,11H2,1H3/t14-,15+,16+,17-,18+,20-/m0/s1

Upstream product

• 472-54-8 19-norprogesterone 
• 1778-02-5 Pregnenolone acetate 
• 6901-40-2 19,21-dihydroxypregn-4-ene-3,20-dione 21-acetate 
• 2723-07-1 5-Bromo-6β-hydroxy-20-oxo-5α-pregnan-3β-yl acetate 
• 2863-88-9 3-ethoxy-19-nor-3,5-androstadiene-17-one 
• 65078-08-2 (Z)-3,20-dimethoxy-21-hydroxy-19-norpregna-1,3,5⁽¹⁰⁾,17⁽²⁰⁾-tetraene 
• 14667-20-0 21-acetoxypregn-4-ene-3,20-dione-19-oic acid 
• 74824-66-1 19-nordeoxycorticosterone 3,20-bis(1,3-propanedithiyl acetal) 
• 135399-04-1 (+)-11-deoxy-19-corticosterone benzoate 
• 88378-35-2 19-oxo-11-deoxycorticosterone acetate 
• 4682-71-7 21-acetoxy-19-nor-pregn-4-ene-3,20-dione 
• 6795-60-4 17-hydroxy-19-nor-17α-pregna-4,20-dien-3-one 
• 68-22-4 norethisterone 
• 130506-56-8 Benzoic acid (S)-2-hydroxy-2-((8R,9S,10R,13S,14S,17S)-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl ester 

Relevant academic research and scientific papers

A Practical Route for Enantioselective Total Synthesis of (+)-11-Deoxy-19-norcorticosterone via Intramolecular Diels-Alder Addition to an ortho-Quinodimethane

A convenient and practical route for enantioselective synthesis of the A-nor-B-trienic steroid 2 via an intramolecular cycloaddition of the olefinic ortho-quinodimethane 3 generated in situ by thermolysis of the olefinic benzocyclobutene 4 is report

Process for the synthesis of the hydroxyacetyl side-chain of steroids of the pregnane type, novel 21-hydroxy-20-oxo-17α-pregnane compounds and pharmaceutical preparations containing them

The present invention relates to a novel general process for synthesizing a α- or β-oriented hydroxyacetyl side chain of steroids of the pregnane type, which comprises treating a corresponding steroid carbaldehyde in succession with formaldehyde dimethylmercaptal-S-oxide in the form of an alkali metal salt thereof, and with a strongly acid hydrolysing agent.Preferred final products are compounds of the formula STR1 wherein n is 1 or 2, R 2 represents methyl or difluoromethyl, and R 1 represents hydroxymethyl, methoxymethyl, acetoxymethyl or hydrogen, and, if n is 2 and/or R 2 is difluoromethyl, R 1 also represents methyl. These compounds act as agonists or antagonists of natural steroid hormones. The antigestagenic 19,21-dihydroxy-17α-pregn-4-ene-3,20-dione and its 6,7-dehydro derivatives and diacetates are of particular interest.

New Syntheses of 19,21-Dihydropregn-4-ene-3,20-dione, 21-Hydroxy-19-norpregn-4-ene-3,20-dione, and 11β,19,21-trihydroxypregn-4-ene-3,20-dione

19,21-Dihydroxypregn-4-ene-3,20-dione has been synthesized from 3β-acetoxypregn-5-en-20-one via the "hypoiodite reaction" , and Henbest acetoxylation at C-21; oxidation of the intermediate 21-monoacetate to 19-oxo derivative and alkaline cleavage gave 21-hydroxy-19-norpregn-4-ene-3,20-dione.A similar synthesis of 11β,19,21-trihydroxypregn-4-ene-3,20-dione from 3β-acetoxypregn-5-ene-11,20-dione proceeded through intermediates with the 11β-hydroxy function protected as its acetate.Unusual features mainly of conformational origin were observed in the presence of the 11β-acetoxy substituent; some were helpful to the synthesis, while others led to undesirable side reactions.

Simple Route for Elaboration of the Hydroxy-ketone and Dihydroxy-acetone Side-chains of Corticosteroids from 17-Oxo-steroids

α-Formylaminoacrylic esters, produced by the condensation of ethyl isocyanoacetate with 17-oxo-steroids have been reduced selectively to give the corresponding alcohols; the latter gave, in high yield, the hydroxyacetyl side-chain on acidic hydrolysis or the dihydroxy-acetone side-chain after appropriate oxidation and hydrolysis.