7254-03-7

Usage

Uses

Used in Pharmaceutical Research and Development:
(3S,8S,9S,10R,13S,14S,17S)-3-HYDROXY-10,13-DIMETHYL-2,3,4,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHRENE-17-CARBOXYLIC ACID METHYL ESTER is used as a research compound for exploring its potential biological and pharmacological properties. Its complex structure and stereoisomeric configuration make it a promising candidate for the development of new drugs and therapies.
Used in Chemical Industry:
(3S,8S,9S,10R,13S,14S,17S)-3-HYDROXY-10,13-DIMETHYL-2,3,4,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHRENE-17-CARBOXYLIC ACID METHYL ESTER is used as a chemical intermediate in the synthesis of other complex organic compounds. Its unique structure and functional groups can be utilized in the development of new chemical products and materials.

InChI:InChI=1/C21H32O3/c1-20-10-8-14(22)12-13(20)4-5-15-16-6-7-18(19(23)24-3)21(16,2)11-9-17(15)20/h4,14-18,22H,5-12H2,1-3H3/t14-,15-,16-,17-,18+,20-,21-/m0/s1

Upstream product

• 4139-90-6 (3S,8S,9S,10R,13S,14S,17S)-3-Acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid methyl ester 
• 514-50-1 3β-acetoxy-5α,6β-dibromocholestane 
• 15173-68-9 etienic acid 
• 75-36-5 acetyl chloride 
• 67-56-1 methanol 
• 73672-02-3 pregnenolone 21-pyridinium iodide 
• 616-38-6 carbonic acid dimethyl ester 
• 432027-36-6 3β-acetoxy-20-methyl-21.21-diphenyl-pregnadiene-(5.20) 
• 7150-18-7 3β-acetoxyetienic acid 
• 1778-02-5 Pregnenolone acetate 
• 145-13-1 Pregnenolone 
• 25493-69-0 (4aS,6aS,6bR,10S,12aR)-methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 

Downstream Products

• 1164-98-3 21-hydroxypregnenolone 
• 96273-69-7 3β-benzoyloxy-androstene-(5)-carboxylic acid-(17β)-methyl ester 
• 2681-55-2 3-oxo-androst-4-ene-17β-carboxylic acid methyl ester 
• 145-13-1 Pregnenolone 
• 2097-74-7 3β-Triphenylmethyloxy-androst-5-en-17-β-carbonsaeure-methylester 
• 160001-82-1 (1S,3aS,4S,5S,7aS)-4-Chlorocarbonylmethyl-7a-methyl-5-((1R,4S)-1-methyl-2-oxo-4-triisopropylsilanyloxy-cyclohexyl)-octahydro-indene-1-carboxylic acid methyl ester 
• 151520-57-9 (1S,3aS,4S,5S,7aS)-4-Carboxymethyl-7a-methyl-5-((1R,4S)-1-methyl-2-oxo-4-triisopropylsilanyloxy-cyclohexyl)-octahydro-indene-1-carboxylic acid methyl ester 
• 116934-48-6 methyl 3-oxo-androst-4,6-diene-17β-carboxylate 
• 1402153-80-3 (2R,8S,9S,10R,13S,14S,17S)-2-(4-chlorobenzyl)-17-(4-hydroxybenzoyl)-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylic acid 
• 1402154-12-4 (2R,8S,9S,10R,13S,14S,17S)-methyl 2-(4-chlorobenzyl)-17-(4-hydroxybenzoyl)-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate 
• 1402154-11-3 (2R,8S,9S,10R,13S,14S,17S)-methyl 17-(4-hydroxybenzoyl)-2,10,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate 
• 1402154-05-5 (2R,8S,9S,10R,13S,14S,17S)-methyl 2-(4-chlorobenzyl)-10,13-dimethyl-17-[(pyridin-2-ylthio)carbonyl]-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate 
• 1402154-08-8 (2R,8S,9S,10R,13S,14S,17S)-methyl 2-benzyl-10,13-dimethyl-17-[(pyridin-2-ylthio)carbonyl]-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate 
• 1402153-98-3 (2R,8S,9S,10R,13S,14S,17S)-2-(4-chlorobenzyl)-3-(methoxycarbonyl)-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid 

Relevant academic research and scientific papers

Discovery of novel 3-hydroxyandrosta-5,7-Diene-17-Carboxylic acid derivatives as anti-inflammatory bowel diseases (IBD) agents

A series of steroidal compounds based on 3-hydroxyandrosta-5,7-diene-17-carboxylic acid core structure were designed, synthesized and bio-evaluated for their anti-inflammatory potency. Among them, compound 5c, 6f, and 6q effectively inhibited the producti

AZASTEROIDS FOR TREATMENT OF TUBERCULOSIS

The present invention provides a compound having the structure: formula (I), for use in combinatoin with an anti-tuberculosis drug for treating a subject infected with M. tuberculosis.

3-hydroxy-5-androstene -17 β method for the preparation of carboxylic acid methyl ester

The invention discloses a 3-hydroxy-5-androstene-17 beta carboxylate (I) preparation method comprising the steps of: 3-hydroxy-5-androstene-17 beta carboxylic acid (II) is dissolved in alkali water, and added with dimethyl carbonate, and heated for reflux for esterification reaction, an alkali solution is added in the esterification reaction process every 20-40min to adjust the PH value to 8-10, after points are dispensed on a plate for reaction, circulating water is cooled to 65 to 75 DEG C, an acid is used to adjust the PH value to 6-8, vacuum concentration of excess dimethyl carbonate is performed, circulating water is cooled to below 40 DEG C, and 3-hydroxy-5-androstene-17 beta carboxylate (I) is obtained by direct spin-filtering, water washing to neutral, and spin-drying. The method avoids the use of highly corrosive strong acids and highly toxic methanol for esterification and use of hypertoxic dimethyl sulfate for esterification, and has the advantages of good quality, high yield, low cost, economy, environmental protection, simple after treatment.

An efficient approach to novel 17-5′-(1′,2′,4′)- oxadiazolyl androstenes via the cyclodehydration of cytotoxic O-steroidacylamidoximes, and an evaluation of their inhibitory action on 17α-hydroxylase/C17,20-lyase

Novel 17-exo-oxadiazoles in the androst-5-ene series were efficiently synthesized in a two-step sequence via the corresponding O-acylamidoxime intermediates (obtained from steroidal 17-carboxylic acids and amidoximes in the presence of coupling reagent), which then underwent tetrabutylammonium fluoride-induced cyclocondensation under mild reaction conditions. The synthesized compounds were subjected to in vitro pharmacological studies to investigate their inhibitory effect on rat testicular C17,20-lyase and their antiproliferative action on four malignant human adherent cell lines (HeLa, MCF7, A2780 and A431). One of the oxadiazolyl derivatives proved to exert significant enzyme-inhibitory action (IC50 = 0.60 μM), while some of the isolated O-acylated amidoxime intermediates displayed high cytotoxic activities on all examined cell lines, with IC50 values in the range 0.22-3.94 μM.

The first synthesis of Krempene B

The synthesis of Krempene B, which can be isolated from the marine soft coral Cladiella krempfi, is achieved in 23.9% overall yield from commercially available 3β-acetoxy-5-pregnen-20-one by 11 steps. Key transformations include the dienone-phenol rearrangement of steroids and Wittig reaction.

Design and diastereoselective synthesis of C-2,C-20-diaryl steroidal derivatives

A novel and efficient synthetic strategy to access unique C-2 substituted steroid analogues 3 and 4 is described. The unusual C-2 aryl ether analogues 3 were shown to act as virtual antagonists of LRH-1 and were prepared as single diastereoisomers, employing a fifteen-step sequence from pregnenolone (9). The key steps include the stereoconvergent nucleophilic displacement of an epimeric mixture of 3-keto 2-bromo steroids, chemoselective carbonylation of an enol triflate and conversion of a thiopyridyl ester into an aryl ketone. The related C-2 benzyl analogues 4 were prepared in a similar manner. Starting from pregnenolone, a diastereoselective fifteen-step synthesis was developed to access novel C-2-substituted steroid analogues. A range of C-2 benzyl and aryl ether analogues were prepared to probe their efficacy as antagonists of the nuclear receptor LRH-1. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Dimethylaluminum methyltellurate, a new reagent for the cleavage of hindered methyl esters under exceptionally mild conditions by a novel mechanism

An efficient and effective new reagent (Me2AlTeMe)2 has been developed for the conversion of methyl esters to the corresponding carboxylic acids in toluene solution at 23°C.

Steroidal Aphidicolin Analogues Derived from Pregnenolone

The converision of pregnenolone into the 3β,5α-, 3α,5α-, 4β,5α-, 3β,4α, 3α,4β- and 3α,4α-dihydroxy derivatives of 17β-hydroxymethyl-5α-androstane as steroidal analogues of the diterpenoid DNA polymerase α inhibitor, aphidicolin, is described.

Anti-AIDS agents. Part 36: 17-carboxylated steroids as potential anti-HIV agents

In our search for novel anti-HIV agents, seven 17-carboxylated steroid derivatives were synthesized and evaluated as potential anti-HIV agents. Compound 13 exhibited potent anti-HIV activity in acutely infected H9 lymphocytes with EC50 and therapeutic index values of 0.8 μM and 300, respectively.

Synthesis of 4-trifluoromethylsteroids: A novel class of steroid 5α-reductase inhibitors

A concise synthetic approach to 4-trifluoromethyl steroids, a novel class of steroid 5α-reductase inhibitors, is described. Direct trifluoromethylation of steroid olefinic bromide with methyl fluorosulfonyldifluoroacetate was used as a key step in the synthesis. The compound 4 exhibited highly inhibitory activity than Finasteride in in vitro assay.