1759-35-9

Basic information

• Product Name: 3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid
• Synonyms: (3S,3aS,5aS,6R,9aS,9bS)-Dodecahydro-3-hydroxy-3a,6-diMethyl-7-oxo-1H-benz[e]indene-6-propanoic Acid;[3S-(3α,3aα,5aβ,6β,9aα,9bβ)]-Dodecahydro-3-hydroxy-3a,6-diMethyl-7-oxo-1H-benz[e]indene-6-propanoic Acid;17β-Hydroxy-5-oxo-A-nor-3,5-secoandrostan-3-oic Acid;3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid;4-Nor-3,5-seco-5-oxo-17β-hydroxyandrostan-3-oic Acid
• CAS NO: 1759-35-9
• Molecular Formula: C₁₈H₂₈O₄
• Molecular Weight: 308.41252
• Mol File: 1759-35-9.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid(1759-35-9)
• EPA Substance Registry System: 3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid(1759-35-9)

Safety Data

• Hazardous Substances Data: 1759-35-9(Hazardous Substances Data)

Usage

Description

3,5-Seco-A-norandrostan-17β-ol-5-on-3-oic Acid, also known as 4-Nor-3,5-seco-5-oxo-17β-hydroxyandrostan-3-oic Acid, is an open A-ring steroid derived from the modification of the steroidal structure. It has been identified for its inhibitory activity on hormone binding, specifically from an extract of Nippostrongylus brasiliensis, a parasitic nematode. This unique chemical property positions it as a potential candidate for various applications in the pharmaceutical and chemical industries.

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

Downstream Products

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

Relevant articles and documents

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.

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

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.