17243-87-7

Usage

Uses

Used in Pharmaceutical Industry:
(16E)-3-hydroxy-16-(phenylmethylidene)androst-5-en-17-one is used as a pharmaceutical intermediate for the development of drugs targeting hormonal imbalances and related conditions. Its structural similarity to androstenedione, a key hormone in the biosynthesis of testosterone and estrone, makes it a promising candidate for research and development in this field.
Used in Steroid Chemistry Research:
As a derivative of androstenedione, (16E)-3-hydroxy-16-(phenylmethylidene)androst-5-en-17-one is utilized in the study of steroid chemistry to understand the structure-activity relationships and the potential modifications that can be made to enhance or alter its biological activities.
Used in Hormone Replacement Therapy:
(16E)-3-hydroxy-16-(phenylmethylidene)androst-5-en-17-one may be employed in hormone replacement therapies, given its relation to androstenedione, which plays a crucial role in the production of testosterone and estrone. Its potential use in this area would require further investigation into its safety and efficacy.

Upstream product

• 53-43-0 dehydroepiandrosterone 
• 100-52-7 benzaldehyde 
• 853-23-6 prasterone acetate 
• 17243-79-7 3β-Acetoxy-17α-hydroxy-16β.17β-(1-phenyl-3-oxo-trimethylen)-androsten-(5) 
• 17243-84-4 3β,17α-Dihydroxy-16β,17β-(1-phenyl-2-hydroxymethylen-3-oxo-trimethylen)-androst-5-en 
• 17243-85-5 α-<3β-Acetoxy-17-oxo-Δ⁵-androsten-16ξ-yl>-phenylessigsaeure-methylester 

Downstream Products

• 1369581-64-5 3β-hydroxy-5-en-7'-phenyl-androstano[17,16-d][1,2,4]triazolo[1,5-a]pyrimidine 
• 129908-91-4 16-benzylidene-17-oxo-5-androsten-3β-yl acetate 
• 1428382-38-0 C₄₁H₄₃NO₃S 

Relevant academic research and scientific papers

Androsterone-based gels enable diastereospecific reductions and diastereoselective epoxidations of gelators

Eleven new androsterone-based gelators were synthesized, and their gelation properties and gel-mediated reactions were investigated. The relationships between the structures, gelation and self-assembly processes of the gelators are discussed. By using granular PTFE (polytetrafluoroethylene) as costirrers, quantitative and diastereospecific reductions of the gelator carbonyl groups mediated by water were achieved in the gels of seven gelators. This reduction did not occur in the control experiment which used organic solvent-mediated conventional conditions. The diastereospecific and quantitative reductions possibly occur via a hydrogen-bonded-activated carbonyl mechanism. Five of the gelators underwent gel-mediated epoxidation and the products were more diastereoselective than those obtained using conventional epoxidation reactions. This can be attributed to the ordered arrangements in the gels.

Facile preparation and preliminary cytotoxicity evaluation of dehydroepiandrosterone C-16 spiro-pyrrolidine derivatives

A facile synthesis of dehydroepiandrosterones derived by C-16 spiro-pyrrolidine and their cytotoxic evaluation are reported. Seven derivatives, 3a–3g, were prepared by the [3 + 2] cycloaddition reaction of the 16-arylidene dehydroepiandrosterone and the a

Neighboring heteroatom effect unique to aqueous aldol reactions of water-insoluble substrates

The reactions of ketones and aldehydes in the presence of Li+ and in the presence or absence of PTC mediated by water were performed to produce aldol products. Several advantages of the aqueous reactions over organic solvent-mediated ones have been demonstrated including higher yields, shorter reaction times, simpler purifications, and better functional group tolerance. Some reactions that do not take place in organic solvents have been realized in water. The successes are attributed to the neighboring heteroatom effect. In the aqueous aldol condensations, Li2CO3 was an efficient catalyst, and therefore base-liable groups such as epoxides, esters, and silyl groups could survive. For heteroaromatic ethanones, the aqueous aldol reactions were accomplished without PTC to give β-hydroxyketones in good yields. The water-mediated condensations of aldosyl hemiacetals with aromatic ketones led to a new carbohydrate-derived skeleton in quantitative yields. To some extent, this research has expanded the applicablities of aldol condensations and reactions.

Design, synthesis and biological evaluation of novel steroidal spiro-oxindoles as potent antiproliferative agents

Two series of novel steroidal spiro-pyrrolidinyl oxindoles 3a-t and 6a-c were designed and synthesized from dehydroepiandrosterone using the 1,3-dipolar cycloaddition as the key step and further evaluated for their antiproliferative activities for four human cancer cell lines (MGC-803, EC109, SMMC-7721 and MCF-7). This protocol achieved the formation of two CC bonds, one CN bond and the creation of one new five-membered pyrrolidine ring and three contiguous stereocenters in a single operation. Biological evaluation showed that these synthesized steroidal spiro-pyrrolidinyl oxindoles possessed moderate to good antiproliferative activities against the tested cell lines and some of them were more potent than 5-Fu. Particularly, compound 3g showed good antiproliferative activity against SMMC-7721 (IC50 = 0.71 μM). Steroid dimer 6b showed improved antiproliferative activities against SMMC-7721 and MCF-7 with the IC50 values of 4.30 and 2.06 μM, respectively. Flow cytometry analysis demonstrated that compound 3n caused the cellular early apoptosis and cell cycle arrest at G2/M phase in a concentration- and time-independent manner.

Synthesis of novel 16-spiro steroids: Spiro-7′-(aryl)tetrahydro-1H- pyrrolo[1,2-c][1,3]thiazolo-trans-androsterone hybrid heterocycles

The 1,3-dipolar cycloaddition of azomethine ylide derived in situ from the reaction of acenaphthylene-1,2-dione and 1,3-thiazolane-4-carboxylic acid to various exocyclic dipolarophiles synthesized from trans-androsterone and trans-dehydroandrosterone afforded a library of novel spiro[5′.2″] acenaphthylene-1″-one-spiro[16.6′]-(7′-aryl) -tetrahydro-1H-pyrrolo [1,2-c][1,3]thiazolo-trans-androsterone/ dehydroandrosterone hybrid heterocycles respectively. These reactions proceeded stereo-specifically affording a single isomer of the 16-spiro steroids in excellent yields.

Synthesis of novel D-ring fused 7′-aryl-androstano[17,16-d][1,2,4] triazolo[1,5-a]pyrimidines

The preparation of novel steroidal heterocycles containing the 7-aryl-substituted 1,2,4-triazolo[1,5-a]pyrimidine moiety fused to the 16,17-positions of the steroid nucleus is described. The Aldol reaction of 4-aza-androst-3,17-dione (1a) and dehydroepiandrosterone (DHEA, 1b) with aromatic aldehydes was catalyzed by KF/Al2O3 to give the corresponding 3-oxo-4-aza-5α- and 3β-hydroxy-5-en-16-arylidene-17- ketosteroids (2a-r). Subsequently, the intermediates 2a-r reacted with dinucleophilic 3-amino-1,2,4-triazole in presence of t-BuOK to afford the title compounds (3a-r). All the synthesized heterosteroids are new and are currently being evaluated for their biological activities.