1759-35-9

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid is used as a precursor in the synthesis of heterocyclic steroids for various therapeutic applications. Its ability to inhibit hormone binding makes it a valuable compound in the development of drugs targeting hormonal imbalances and related conditions.
Used in Chemical Research:
In the field of chemical research, 3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid serves as a key intermediate for the creation of novel steroidal compounds. Its unique structure allows for further modification and exploration of new chemical entities with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Hormone Regulation:
3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid is used as a research tool for understanding the mechanisms of hormone binding and action. Its inhibitory activity on hormone binding can provide insights into the development of new drugs that target hormone receptors, which may be beneficial in treating conditions related to hormonal imbalances or disorders.

Upstream product

• 58-22-0 testosterone 
• 1045-69-8 testosterone acetate 
• 10028-15-6 ozone 
• 64-19-7 acetic acid 
• 1458-92-0 17β-acetoxy-4-oxa-androst-5-en-3-one 
• 57-85-2 testosterone propionate 
• 3510-18-7 5-oxo-17β-propionyloxy-4-nor-3,5-secoandrostan-3-oic acid 
• 68634-62-8 17β-Acetoxy-3,6-cyclo-A-nor-3,5-seco-6β-androstan-3,5-dion 

Downstream Products

• 24124-88-7 3,3-Diphenyl-A-nor-3,5-seco-androstan-3,17β-diol 
• 24124-87-6 17β-Acetoxy-3,3-diphenyl-A-nor-3,5-seco-androsten-(2) 
• 1353000-88-0 17β-hydroxy-4-(4-fluorophenyl)-4-aza-5-androsten-3-one 
• 1353000-97-1 17β-hydroxy-4-(4-tolyl)-4-aza-5-androsten-3-one 
• 795-83-5 4-methyltestosterone 
• 326864-87-3 methyl 17β-(tert-butyldimethylsilyloxy)-2-phenylseleno-5,5-ethylenedioxy-3,5-seco-4-norandrostan-3-oate 
• 92472-37-2 17β-hydroxy-4-methyl-4-aza-5-androsten-3-one 
• 54155-67-8 17β-hydroxy-5-hydroxyimino-3,5-seco-A-nor-androstanoic acid-(3) 

Relevant academic research and scientific papers

Investigations on 16-Arylideno Steroids as a New Class of Neuroprotective Agents for the Treatment of Alzheimer’s and Parkinson’s Diseases

Neuroinflammatory mechanisms mediated by activated glial and cytokines (TNF-α, IL-1β) might contribute to neuronal degeneration leading to Alzheimer’s (AD) and Parkinson’s disease (PD). Lipopolysaccharide (LPS) is an inflammogen derived from the cell wall of Gram-negative bacteria, which promotes neuroinflammation and subsequent neurodegeneration. Dehydroepiandrosterone (DHEA) and testosterone have been reported as neuroprotective steroids useful for the treatment of various neurodegenerative disorders. In the present study, several 16-arylidene steroidal derivatives have been evaluated as neuroprotective agents in LPS-treated animal models. It was observed that 16-arylidene steroidal derivatives 1a-d and 6a-h considerably improve LPS-induced learning, memory, and movement deficits in animal models. Biochemical estimations of brain serum of treated animals revealed suppression of oxidative and nitrosative stress, acetylcholinesterase activity, and reduction in TNF-α levels, which were induced through LPS mediated neuroinflammatory mechanisms leading to neurodegeneration of brain. Of all the steroidal derivatives, 16-(4-pyridylidene) steroid 1c and its 4-aza analogue 6c were found to be the most active neuroprotective agents and produced effects comparable to standard drug celecoxib at a much lower dose and better than dexamethasone at the same dose in terms of behavioral, biochemical, and molecular aspects.

Beyond Pseudo-natural Products: Sequential Ugi/Pictet-Spengler Reactions Leading to Steroidal Pyrazinoisoquinolines That Trigger Caspase-Independent Death in HepG2 Cells

In this work, we describe how stereochemically complex polycyclic compounds can be generated by applying a synthetic sequence comprising an intramolecular Ugi reaction followed by a Pictet-Spengler cyclization on steroid-derived scaffolds. The resulting compounds, which combine a fragment derived from a natural product and a scaffold not found in nature. are both structurally distinct and globally similar to natural products at the same time, and interrogate an alternative region of the chemical space. One of the new compounds showed significant antiproliferative activity on HepG2 cells through a caspase-independent cell-death mechanism, an appealing feature when new antitumor compounds are searched.

Design, synthesis, and biological evaluation of 16-substituted 4-azasteroids as tissue-Selective Androgen Receptor Modulators (SARMs)

A novel series of 16-substituted-4-azasteroids has been identified as potential tissue-selective androgen receptor modulators. These ligands display potenthARbinding and agonist activity, low virilizing potential, and good pharmacokinetic profiles in dogs

A microwave promoted and Lewis acid catalysed solventless approach to 4-azasteroids

The preparation of 3-oxo-4-azasteroid from A-nor-3,5-secosteroid-3-oic acid is described in a solventless condition catalysed by Lewis acid under microwave irradiation. We utilized urea as an environmentally benign source for the generation of ammonia for the aza cyclization reaction.

Novel partial synthetic approaches to replace carbons 2,3,4 of steroids. A methodology to label testosterone and progesterone with 13C in the steroid A ring. Part 1

A synthetic route to replace A ring carbon atoms 2, 3 and 4 of steroid hormones is described. Readily available testosterone propionate or progesterone, respectively, are degraded to the corresponding 10-formyl-5-oxo-des-A intermediates, in a first stage to the preparation of 2,3,4-(13C3)-labeled steroids. (C) 2000 Elsevier Science Ltd.

Synthesis and biological activity of azasteroidal [3,2-c]- and [17,16-c]pyrazoles

Cholesterol, testosterone acetate and dehydroepiandrosterone acetate were used as starting materials for the preparation of azasteroidal [3,2-c]- and [17,16-c]pyrazole derivatives. In case of the 4-aza androstane series, a mixture of 5α/5β epimers 8 was obtained, which were separated by chemical methods. The compounds 4, 5, 10, 12, 13, 15, 16 and 18-22 were screened for antiinflammatory activity using the carrageenan rat paw oedema model. Oxirane 22 was found to be around ten times more potent than hydrocortisone. Evaluation of compounds 14, 18 and 19 for their antineoplastic activity was also carried out at the National Cancer Institute, Bethesda, MD, USA, using standard procedures.

Azasteroids as Inhibitors of Rat Prostatic 5α-Reductase

A series of A-ring heterocyclic steroids has been prepared and tested for inhibition of rat prostatic steroid 5α-reductase in vitro.Strinkingly high inhibitory activity was found with a group of 17β-substituted 4-methyl-4-aza-5α-androstan-3-ones.These compounds were prepared from 3-keto-Δ4-precursors by oxidative (O3 or NaIO4-KMnO4) A-ring cleavage followed, in turn, by ring closure with an amine and hydrogenation over platinum catalyst.Other A-ring azasteroids were made by Beckmann rearrangement of oximes of 2-oxo-A-nor-, 3-oxo- and 4-oxo-5α-androstanes.An A-nor-2-oxo-3-azasteroid was prepared by oxidative decarbonylation of a precursor 2,3-dioxo-4-azasteroid with m-chloroperbenzoic acid.A-ring modifications of the 4-azasteroids included Δ1-unsaturation, 2- and 4-substituents, and 3-carbonyl replacements.Side chains at the 17-position were varied with an emphasis on carboxylate derivatives (salts, esters, and amides).