63015-10-1

Usage

Uses

Used in Pheromone-based Product Development:
Androstenone hydrazone is utilized as a key ingredient in the formulation of pheromone-based products, leveraging its role in olfactory signaling to potentially influence social interactions and mating behavior.
Used in Chemical Ecology Research:
In the field of chemical ecology, Androstenone hydrazone is employed as a subject of study to understand its role in animal communication, behavior, and social dynamics, providing insights into the complex interactions between chemical signals and biological responses.
Used in Neurobiology and Neuroendocrinology Research:
Androstenone hydrazone is applied as a research tool in neurobiology and neuroendocrinology to explore its effects on the brain and behavior, contributing to the advancement of knowledge regarding the interplay between chemical signals and neural processes.

Upstream product

• 53-43-0 dehydroepiandrosterone 
• 853-23-6 prasterone acetate 
• 53-43-0 dehydroepiandrosterone 

Downstream Products

• 32138-69-5 17-Iodandrosta-5,16-dien-3β-ol 
• 32138-69-5 17-iodo-5,16-androstadien-3-ol 
• 86770-60-7 17,17-diiodo-3β-hydroxy-5-androstene 
• 91414-16-3 3β-hydroxy-17-phenylselenoandrosta-5,16-diene 
• 53-43-0 dehydroepiandrosterone 
• 114474-49-6 17-bromo-3β-hydroxy-17-selenophenylandrost-5-ene 
• 154229-21-7 17-(3-pyridine)-4,16-dieneandrost-3-one 
• 154229-18-2 abiraterone acetate 
• 154229-19-3 abiraterone 

Relevant academic research and scientific papers

Synthesis, characterization and antitumor activities of some steroidal derivatives with side chain of 17-hydrazone aromatic heterocycle

Here a series of dehydroepiandrosterone-17-hydrazone and estrone-17-hydrazone derivatives possessing various aromatic heterocycle structures in 17-side chain of their steroidal nucleus were synthesized and their structures were evaluated. The antiproliferative activity of synthesized compounds against some cancer cells was investigated. The results have demonstrated that some dehydroepiandrosterone-17-hydrazone derivatives show distinct antiproliferative activity against some cancer cells through inducing cancer cell apoptosis, and compound 8 with a quinoline structure in 17-side chain displays excellent antiproliferative activity in vitro against SGC 7901 cancer cell (human gastric carcinoma) with an IC50 value of 1 μM. In addition, estrone-17-hydrazone derivatives having a key feature of indole group in the structure showed a special obvious cytotoxicity against HeLa cells, but almost inactive against other cells. The information obtained from the studies is valuable for the design of novel steroidal chemotherapeutic drugs.

Intramolecular sensitization within steroids: Excited-state interaction of C-17 α and β carbon-bromine bonds with a C-6 carbonyl group

The synthesis, photochemistry, and photophysics of 17α-bromo-3α -(triphenylsilyloxy)-5α-androstan-6-one (1) and 17β-bromo-3β -(triphenylsilyloxy)-5α-androstan-6-one (2) have been studied in aqueous tetrahydrofuran. The 17α-bromo isomer gives evidence (red

Discovery of novel isatin-dehydroepiandrosterone conjugates as potential anticancer agents

A series of isatin-dehydroepiandrosterone hybrids were synthesised via a convenient condensation procedure, and which were evaluated for their potential anticancer activities. The preliminary assays indicated that some of the newly obtained compounds exhi

Synthetic method of abiraterone acetate and intermediate thereof (by machine translation)

The invention relates to a synthesis method of abiraterone acetate and a dragon intermediate thereof. In the synthesis method of abiraterone acetate intermediate, a compound of formula (I), a chloro reagent and a base are chlorinated to obtain the abiraterone acetate intermediate of formula (II). The mass ratio of the compound of the formula (I) to the base is 1: (1.5 -3). The structure of the compound of formula (I) and abiraterone acetate is as follows. To the synthesis method, the occurrence probability of side reactions in the chlorination reaction process can be reduced while the high reaction activity is maintained, so that the yield and purity of the abiraterone acetate intermediate can be improved, and the process is simple. (by machine translation)

Dimerization androst compound and its preparation method, pharmaceutical composition and application

Dimeric androstane type compounds shown as the formula (I) are disclosed. Definitions of R1 and R2 are described in the specification. A preparing method, a pharmaceutical composition and applications of the dimeric androstane type compounds are further disclosed.

A method for preparing abiraterone acetate (by machine translation)

The invention relates to a method for preparing abiraterone acetate, the method is to dehydrogenation epandrosterone as raw materials, with hydrazine hydrate, iodine response, to obtain 17-iodo-androst -5,16-diene -3 β-ol, then the under the catalysis of palladium benzene phosphine base43 with 3-pyridine zinc halide occurs arab League bit dragon Negishi coupling reaction, the final with acetyl chloride or acetic anhydride esterification, to obtain the target product abiraterone acetate. (by machine translation)

Compound with anti-tumor activity and application of compound

The invention discloses an amino-acid-oriented steroid small peptide compound with anti-tumor activity.The structure of the compound is shown in the general formula I.Corresponding hydrazone and oxime are synthesized with dehydroepiandrosterone (DHEA), DHEA and an amino acid derivative are then condensed, and the compound is obtained.The compound has a remarkable inhibiting effect on growth of tumor cells especially human hepatoma cells, human lung cancer cells and human melanoma cells, and can serve as an active ingredient for anti-tumor medicine to be applied to prevention and treatment of cancer.

Dehydro epandrosterone aromatic aldehyde azine steroid compound and its synthetic method and application in the preparation of antineoplastic

The invention relates to a dehydroepiandrosterone aromatic aldehyde azine steroidal compound with an azine structure. The chemical structural formula is as shown by dehydroepiandrosterone acetone azine (1), dehydroepiandrosterone benzaldehyde azine (2), dehydroepiandrosterone-3-pyridylaldehyde azine (3), dehydroepiandrosterone-3-thiophenecarboxaldehyde azine (4), dehydroepiandrosterone-3-hydroxybenzaldehyde azine (5), dehydroepiandrosterone-2-naphthaldehyde azine (6), dehydroepiandrosterone-4-quinolinecarboxaldehyde azine (7) and dehydroepiandrosterone-6-methoxy-naphthaldehyde azine (8) described in the specification. Experiments prove that the dehydroepiandrosterone aromatic aldehyde azine steroidal compound has an obvious inhibitory effect on various tumor cell strains, and can be applied to preparation of drugs for treating cancers.

A-ring modified steroidal azoles retaining similar potent and slowly reversible CYP17A1 inhibition as abiraterone

Abiraterone acetate is a potent inhibitor of human cytochrome P450c17 (CYP17A1, 17α-hydroxylase/17,20-lyase) and is clinically used in combination with prednisone for the treatment of castration-resistant prostate cancer. Although many studies have documented the potency of abiraterone (Abi) in a variety of in vitro and in vivo systems for several species, the exact potency of Abi for human CYP17A1 enzyme has not yet been determined, and the structural requirements for high-potency steroidal azole inhibitors are not established. We synthesized 4 Abi analogs differing in the A-B ring substitution patterns: 3α-hydroxy-Δ4-Abi (13), 3-keto- Δ4-Abi (11), 3-keto-5α-Abi (6), and 3α-hydroxy- 5α-Abi (5). We measured the spectral binding constants (Ks) using purified and modified human CYP17A1 along with the determination constants (Ki) applying a native human CYP17A1 enzyme in yeast microsomes for these compounds as well as for ketoconazole. For Abi, 3-keto- Δ4-Abi, 3-keto-5α-Abi, and 3α-hydroxy-5α-Abi, the type 2 spectral changes gave the best fit for a quadratic equation, since in these experiments Ks values were 0.1-2.6 nM, much lower than that for ketoconazole and 3α-hydroxy-Δ4-Abi (Ks values were 140 and 1660 nM, respectively). Inhibition experiments showed mixed inhibition patterns with Ki values of 7-80 nM. Abi dissociation from the CYP17A1-Abi complex was incomplete and slow; the t1/2 for dissociation was 1.8 h, with 55% of complex remaining after 5 h. We conclude that Abi and the 3 related steroidal azoles (3-keto-Δ4-Abi, 3-keto-5α-Abi, and 3α-hydroxy-5α-Abi), which also mimic natural substrates, are extraordinarily potent inhibitors of human CYP17A1, whereas the 3α-hydroxy-Δ4-Abi is moderately potent and comparable to ketoconazole.

SYNTHESIS OF ABIRATERONE AND RELATED COMPOUNDS

The present invention relates to processes for obtaining abiraterone and derivatives thereof, such as abiraterone acetate, by means of a Suzuki coupling through a steroid borate of general formula (IV) or a C—C coupling through a steroid hydrazone of general formula (II), as well as to intermediates useful in said processes.