6173-35-9

Usage

Uses

Used in Pharmaceutical Industry:
17β-Acetoxy-2α-broMo-5α-androstanone is used as a pharmaceutical compound for its ability to inhibit progesterone synthesis and dihydrotestosterone binding. This makes it a potential candidate for the development of drugs targeting hormonal imbalances and conditions related to androgen excess, such as hirsutism, polycystic ovary syndrome (PCOS), and certain types of cancer.
Used in Research and Development:
In the field of research and development, 17β-Acetoxy-2α-broMo-5α-androstanone serves as a valuable tool for studying the mechanisms of steroid hormone action, receptor protein interactions, and the role of progesterone and dihydrotestosterone in various physiological processes. Its use in research can lead to a better understanding of these hormones and the development of novel therapeutic strategies.
Used in Steroid Chemistry:
As a steroid analog, 17β-Acetoxy-2α-broMo-5α-androstanone is used in the field of steroid chemistry for the synthesis of other steroidal compounds with potential applications in medicine, agriculture, and other industries. Its unique structure allows for the exploration of new chemical reactions and the development of novel steroidal molecules with tailored properties and functions.
Used in Hormone Regulation:
17β-Acetoxy-2α-broMo-5α-androstanone is used as a hormone regulator, particularly in the context of conditions where the balance of progesterone and dihydrotestosterone is disrupted. By inhibiting their synthesis and binding, 17β-Acetoxy-2α-broMo-5α-androstanone can help restore hormonal balance and alleviate symptoms associated with hormonal imbalances.

Upstream product

• 72272-79-8 17β-acetoxy-2α-bromo-5α-androstan-3β-ol 
• 18000-71-0 17β-acetoxy-2β-bromo-5α-androstan-3-one 
• 1164-91-6 stanolone acetate 
• 110414-84-1 17β-acetoxy-2β-bromo-5α-androstan-3β-ol 
• 39673-22-8 17β-acetoxy-2β-bromo-5α-androstan-3α-ol 
• 981-64-6 (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diyl diacetate 

Downstream Products

• 1236-49-3 5α-androstan-17β-acetate 
• 17780-46-0 17β-Hydroxy-2α,3α-cyclopropano-5α-androstan 
• 981-64-6 3,17β-Diacetoxy-5α-androsten-(2) 

Relevant academic research and scientific papers

The Cephalostatins. 22. Synthesis of bis-steroidal pyrazine pyrones

Cephalostatin 1 (1), a remarkably strong cancer cell growth inhibitory trisdecacyclic, bis-steroidal pyrazine isolated from the marine tube worm Cephalodiscus gilchristi, continues to be an important target for practical total syntheses and a model for the discovery of less complex structural modifications with promising antineoplastic activity. In the present study, the cephalostatin E and F rings were greatly simplified by replacement at C-17 with an α-pyrone (in 12), typical of the steroidal bufodienolides, and by a dihydro-γ- pyrone (in 16). The synthesis of pyrazine 12 from 5α- dihydrotestosterone (nine steps, 8% overall yield) provided the first route to a bis-bufadienolide pyrazine. Dihydro-γ-pyrone 16 was synthesized in eight steps from ketone 13. While only insignificant cancer cell growth inhibitory activity was found for pyrones 12 and 16, the results provided further support for the necessity of more closely approximating the natural D-F ring system of cephalostatin 1 in order to obtain potent antineoplastic activity.

Chemical synthesis of 2β-amino-5α-androstane-3α,17β-diol N-derivatives and their antiproliferative effect on HL-60 human leukemia cells

Even though few steroids are used for the treatment of leukemia, 2β-(4-methylpiperazinyl)-5α-androstane-3α,17β-diol (1) was recently reported for its ability to inhibit the proliferation of human leukemia HL-60 cells. With an efficient procedure that we had developed for the aminolysis of hindered steroidal epoxides, we synthesized a series of 2β-amino-5α-androstane-3α,17β-diol N-derivatives structurally similar to 1. Hence, the opening of 2,3α-epoxy-5α-androstan-17β-diol with primary and secondary amines allowed the synthesis of aminosteroids with diverse length, ramification, and functionalization of the 2β-side chain. Sixty-four steroid derivatives were tested for their capacity to inhibit the proliferation of HL-60 cells; thus obtaining first structure-activity relationship results. Ten aminosteroids with long alkyl chains (7-16 carbons) or bulky groups (diphenyl or adamantyl) have shown antiproliferative activity over 78% at 10 μM and superior to that of the lead compound. The 3,3-diphenylpropylamino, 4-nonylpiperazinyl and octylamino derivatives of 5α-androstane-3α,17β-diol inhibited the HL-60 cell growth with IC50 of 3.1, 4.2 and 6.4 μM, respectively. They were also found to induce the HL-60 cell differentiation.