57072-90-9

Upstream product

• 302-97-6 androst-4-en-3-one-17β-carboxylic acid 

Downstream Products

• 206351-41-9 N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxoandrost-4-ene-17β-carboxamide 
• 206351-44-2 N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxo-4-aza-5α-androstane-17β-carboxamide 
• 166896-74-8 N-tert-butyl-3-oxo-4-aza-5-androsten-17β-formamide 
• 98319-24-5 dihydro-finasteride 
• 98319-26-7 finasteride 
• 206351-42-0 17β-[N-(3'-trifluoromethyl-4'-nitrophenyl)aminocarbonyl]-5-oxo-A-nor-3,5-secoandrostan-3-oic acid 
• 206351-43-1 N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxo-4-azaandrost-5-ene-17β-carboxamide 
• 131267-80-6 N-(1,1-dimethylethyl)-3-oxoandrost-4-ene-17β-carboxamide 
• 53892-00-5 21-Diazoprogesterone 

Relevant academic research and scientific papers

Iridium-Catalyzed Three-component Coupling Reaction of Carbon Dioxide, Amines, and Sulfoxonium Ylides

The first iridium-catalyzed three-component coupling reaction of carbon dioxide, amines, and sulfoxonium ylides has been developed, providing an efficient and straightforward method for the construction of a range of structurally diverse O-β-oxoalkyl carbamates in moderate to excellent yields. This novel protocol features the use of readily available substrates, wide substrate scope, and good functional group tolerance. Moreover, the phosgene-free strategy was successfully applied to the synthesis of a potential antitumor agent.

PROCESS FOR THE PREPARATION OF 17?-SUBSTITUTED-3-OXO-4-AZA-5ALPHA-ANDROSTANE DERIVATIVES

Process for the preparation of 17?-substituted-3-oxo-4-aza-5α-androstane derivatives, which are useful intermediates for the synthesis of 3-oxo-4-aza-5α-androst-1-ene derivatives including finasteride, is provided.

Substrate interaction with 5alpha-reductase enzyme: influence of the 17beta-chain chirality in the mechanism of action of 4-azasteroid inhibitors.

A series of steroidal compounds were synthesized in order to evaluate the possible influence of the configuration of a stereocenter in the 17beta-side chain on the inhibitory activity on the enzyme 5alpha-reductase (5AR). For this purpose diastereomerically pure 4-azasteroids epimers at C-22 were prepared (compounds 1-11) and tested as inhibitors of 5AR in "in vitro" tests. The obtained data showed that in most cases the couples of epimers possess a significant difference in their biological activity. We also considered, for the tested molecules, a series of chemico-physical parameters in order to find a possible correlation with their biological activity. The findings allowed us to propose a model of the binding site of 5AR which comprises also, for 4-azasteroid inhibitors, the configurational aspect of the 17beta-side chain.

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 N-substituted 3-oxo-17β -carboxamide-4-aza-5α-androstanes and the tautomerism of 3-oxo-4-aza-5-androstenes

An N-aryl-3-oxo-4-aza-5α -androst-1-ene-17β carboxamide and three N-aryl or alkyl substituted 17α -hydroxy-3-oxo-4-aza-5α -androstane-17β -carboxamides were synthesized as antiandrogen candidates from 3-oxoandrost-4-ene-17β - carboxylic acid and androst-4-ene-3,17-dione respectively. The chemo- and stereoselective reduction of 3-oxo-4-aza-5-ene intermediates with formic acid and their tautomerism in a solution of chloroform and methanol were described.

Syntheses of [21-11C] and (21-13C)progesterone

[21-11C]Progesterone was synthesised via the cross-coupling 17β-carboxylic acid chloride-4-androsten-3-one with lithium [11C]methyl(2-thienyl)cuprate (LiCN). The title compound was obtained in 30-35% decay corrected radiochemical yield, based on [11C]methyl iodide, within 35 minutes after end of radionuclide production. The specific radioactivity was 14 GBq/μmole. (21-13C)Progesterone was synthesised using the same procedure for determination of the position of the label.

Structure-activity relationships of steroids with mineralocorticoid activity

Fourteen steroid homologues, belonging to the series of 18-substituted progesterone and 17-hydroxymethylketone derivatives were modeled by both molecular and quantum mechanics. We have studied the dependency of the affinity of these compounds for the hMR (human mineralocorticoid receptor) by means of various parameters describing the structure and its molecular properties. Using variable mapping coupled to a discriminant analysis, this work demonstrates the non-linear relationships between affinity and some structural features. We have constructed a model allowing us to predict the affinity and the activity of new compounds. The principal electronic and structural characteristics leading to a selective affinity and activity were revealed.