190006-01-0

Usage

Derived from androstane

17β-(N-tert-butyl)-carbamoyl-5-oxo-A-nor-3,5-secoandrostane-3-oic acid is synthesized from androstane, a steroid hormone.

Synthetic compound

It is a synthetic compound and is not found naturally in the human body.

Norsteroid

It is a modified version of a steroid hormone, specifically a norsteroid.

Research purposes

It is designed for research purposes to study the effects of modifying androstane derivatives on biological processes and hormone signaling pathways.

Tert-butyl carbamoyl group

It has a tert-butyl carbamoyl group attached to the 17β carbon.

Keto group

It has a keto group at the 5 carbon.

Carboxylic acid moiety

It has a carboxylic acid group at the 3 carbon.

Potential applications

As a synthetic norsteroid, it may have potential applications in drug discovery and development for diseases or conditions related to steroid hormone imbalance or dysfunction.

Chemical structure

The specific structure and chemical properties of 17β-(N-tert-butyl)-carbamoyl-5-oxo-A-nor-3,5-secoandrostane-3-oic acid make it useful for studying the effects of modifying androstane derivatives on biological processes and hormone signaling pathways.

Upstream product

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

Downstream Products

• 98319-24-5 dihydro-finasteride 
• 98319-26-7 finasteride 
• 166896-74-8 N-tert-butyl-3-oxo-4-aza-5-androsten-17β-formamide 

Relevant academic research and scientific papers

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.

Design, synthesis and biological evaluation of novel 3-oxo-4-oxa-5α-androst-17β-amide derivatives as dual 5α-reductase inhibitors and androgen receptor antagonists

Prostate cancer (PCa) is the second leading cause of death in men. Recently, some researches have showed that 5α-reductase inhibitors were beneficial in PCa treatment as well. In this study, a series of novel 3-oxo-4-oxa-5α-androst-17β-amide derivatives have been designed and synthesized in a more simple and convenient method. Most of the synthesized compounds displayed good 5α-reductase inhibitory activities and androgen receptor binding affinities. Their anti-proliferation activities in PC-3 and LNCaP cell lines were also evaluated and the results indicated that most of the synthesized compounds exhibited potent anti-proliferative activities. It is obvious that the androgen-dependent cell line LNCaP was much more sensitive than the androgen-independent cell line PC-3. Among all the synthesized compounds, 11d and 11k displayed the best inhibition activity with 4-fold more sensitive toward LNCaP than PC-3, which was consistent with their high affinities observed in AR binding assay. Molecular modeling studies suggested that 11k could bind to AR in a manner similar to the binding of dihydrotestosterone to AR. Compared to the finasteride, 11k showed a longer plasma half-life (4 h) and a better bioavailability. Overall, based on biological activities data, compound 11d and 11k can be identified as potential dual 5α-reductase inhibitors and AR antagonists which might be of therapeutic importance for prostate cancer treatment.