2691-68-1

Usage

InChI:InChI=1/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3-4,13,15-16,20H,5-11H2,1-2H3/t13?,15-,16-,18-,19-/m0/s1

Upstream product

• 64110-61-8 (3β)-3-Acetoxyandrosta-5,7-dien-17-one 
• 146863-67-4 Acetic acid (3S,8R,9S,10R,13S,14S)-7-bromo-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 53-43-0 dehydroepiandrosterone 
• 81968-78-7 3β-hydroxy-5,7-pregnadien-20-one 
• 1177400-16-6 3β-tert-butyldimethylsilyloxy-7α-chloroandrost-5-en-17-one 
• 23668-18-0 7α-bromo-3β-(acetyloxy)androst-5-en-17-one 
• 853-23-6 prasterone acetate 

Downstream Products

• 157522-95-7 (3β,5Z,7E)-9,10-Secocholesta-5,7,10(19),16-tetraen-23-yne-3,25-diol diacetate 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel 5α, 8α-endoperoxide steroidal derivatives with hybrid side chain as anticancer agents

A series of novel 5α, 8α-endoperoxide steroidal hybrid derivatives containing isatin or indole substituents on the C-17 side chain were synthesized and characterized. The preliminary anti-proliferative activity of the compounds against HepG2, MCF-7, HT-29 and HeLa cell lines were investigated. Compounds 7g and 7l displayed significant anti-proliferative activity in vitro against HepG2 and Hela cells, with IC50 values lower than 8 μM. Furthermore, the biological functions of 7g were examined by flow cytometry and colony analysis. The results showed that 7g could induce HepG2 cell apoptosis, inhibited cell cycle progression, and colony growth. The studies indicated that structural modification at C-17 position could be a promising launch point for design steroidal anticancer agents.

Novel steroidal 5α,8α-endoperoxide derivatives with semicarbazone/thiosemicarbazone side-chain as apoptotic inducers through an intrinsic apoptosis pathway: Design, synthesis and biological studies

A series of novel steroidal 5α,8α-endoperoxide derivatives bearing semicarbazone (7a-g) or thiosemicarbazone (7h-k) side chain were designed, synthesized and evaluated for their cytotoxicities in four human cancer cell lines (HepG2, HCT-116, MCF-7, and A549) using the MTT assay in vitro. The results showed that compound 7j exhibited significant cytotoxic activity against HepG2 cells (IC50 = 3.52 μM), being more potent than ergosterol peroxide. Further cellular mechanism studies in HepG2 cells indicated that compound 7j triggered the mitochondrial-mediated apoptosis by decreasing mitochondrial membrane potential (MMP), which was associated with up-regulation of Bax, down-regulation of Bcl-2, activation levels of the caspase cascade, and formation of reactive oxygen species (ROS). The above findings indicated that compound 7j may be used as a promising skeleton for antitumor agents with improved efficacy.

Synthesis and Biological Evaluation of Novel Steroidal 5α,8α-Endoperoxide Derivatives with Aromatic Hydrazone Side Chain as Potential Anticancer Agents

Abstract: Seven new steroidal 5α,8α-endoperoxide derivatives with C-17 aromatic hydrazone side chain were synthesized. Structures of the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectrometry. Anti-proliferative activities of the synthesized compounds were evaluated in vitro by the MTT method. Among the seven compounds, 5α,8α-epidioxy-17-(4-chloro-benzylidene)-hydrazonoandrost-3β-ol showed the strongest anti-proliferative activity against three human cancer cell lines (MCF-7, HepG2, and SK-Hep1).

Synthesis and antitumor activities of steroidal 5α,8α-endoperoxide derivatives with side chain of 17-hydrazone aromatic heterocycle

Here a series of novel 5α,8α-epidioxyandrostan-3β-ol-17-hydrazone derivatives possessing various aromatic heterocycle structures in 17-side chain of their steroidal nucleus were synthesized and characterized. The antiproliferative activity of synthesized compounds against some cancer cells was investigated. The results have demonstrated that compound 8b with quinoline and 8c with indole structure in side chain display excellent anti-proliferative activity in vitro against tested cancer cell lines.

Synthesis and biological evaluation of novel steroidal 5α,8α-epidioxyandrost-6-ene-3β-ol-17-(O-phenylacetamide)oxime derivatives as potential anticancer agents

Inspired by the significant anti-cancer activity of our previously screened natural ergosterol peroxide (EP, 1), we synthesized and characterized a series of novel 5α,8α-epidioxyandrost-3β-ol-17-(O-phenylacetamide)oxime derivatives (9a–o). The anti-proliferative activity of the synthesized compounds against human hepatocellular carcinoma cells (HepG2, Sk-Hep1) and human breast cancer cells (MCF-7, MDA-MB231) were investigated. Compounds 9d, 9f, 9h, 9j and 9m displayed good anti-proliferative activity (most IC50??20?μM) in vitro. Furthermore, fluorescence imaging showed that the designed coumarin-9d conjugate (12) localized mainly in mitochondria, leading to enhanced anticancer activities over the parent structure.

Synthesis and cytotoxic evaluation of steroidal endoperoxide derivatives with hydrazide side chain as anticancer agents

– A series of novel steroidal 5α,8α-endoperoxide derivatives bearing hydrazide side chain were synthesized and evaluated for their cytotoxicities in four human cancer cell lines (HepG2, HCT-116, MCF-7, and A549) using the MTT assay in vitro. The results showed that compound 6k exhibited significant cytotoxic activity against HepG2 cells (IC50 = 5.60 μM). Further cellular mechanism studies in HepG2 cells indicated that compound 6k triggered the mitochondrial-mediated apoptosis by decreasing mitochondrial membrane potential (MMP) which was associated with up-regulation of Bax, down-regulation of Bcl-2.

3beta-hydroxy-5alpha, 8alpha-peroxoandrost-6-en-17-(arring substituted) hydrazone derivative and preparation and application thereof

The invention discloses a 3beta-hydroxy-5alpha, 8alpha -Peroxyandrost-6-en-17-(aromatic ring substituted) hydrazone derivative, preparation and application thereof, and belongs to the technical fieldof medicine chemistry. The structural formula of the 3beta-hydroxy-5alpha, 8alpha -Peroxyandrost-6-en-17-(aromatic ring substituted) hydrazone derivative is shown in the description, wherein R1 represents -CH3, -F, -Cl, -C(CH3)3, -CN, -OCH3, -OH or -H; R2 represents -OC, -H3, -CF3, or -H. Dehydroepiandrosterone is used as the starting material to prepare 3beta -Acetoxy-5-Androstene-17-ketones, followed by bromination and debromination to obtain 3beta-Hydroxyl-5alpha, 8alpha -Peroxyandrost-6-en-17-a hydrazine intermediate , hydrolysis to reduce hydroxyl groups, and then the light is constructed by 5alpha, 8alpha- peroxy bridge which then reacts with hydrazine hydrate to obtain 3beta-Hydroxyl-5alpha, 8alpha -Peroxyandrost-6-en-17-a hydrazine intermediate, and then reacted with hydrazine hydrate to obtain 3beta-Hydroxyl-5alpha, 8alpha -Peroxyandrost-6-en-17-a hydrazine intermediate, and finally the aldehyde amine condensation reaction is carried out to generate 3beta-hydroxyl-5alpha, 8alpha -Peroxyandrost-6-ene-17-(aromatic ring substituted) hydrazone derivatives. The compound has the effects of preventing and treating cancers such as liver cancer, breast cancer and the like.

3beta-hydroxyl-5alpha,8alpha-peroxy-androstane-6-alkene-17-(isatin substituted) hydrazone derivative, as well as preparation and application thereof

The invention discloses a 3beta-hydroxyl-5alpha,8alpha-peroxy-androstane-6-alkene-17-(isatin substituted) hydrazone derivative, as well as preparation and application thereof, belonging to the technical field of medicinal chemistry. The structural formula of the 3beta-hydroxyl-5alpha,8alpha-peroxy-androstane-6-alkene-17-(isatin substituted) hydrazone derivative is as shown in the description, wherein R1 represents -H, -F, -Cl, -Br, -I, -NO2, -OCH3, -OCF3 or -CH3; R2 represents -H, -Cl or -Br. The preparation comprises the following steps: preparing 3beta-acetoxyl-5-androstene-17-ketone by using dehydroepiandrosterone as a raw material; performing bromination reaction and debromination reaction to obtain 3beta-acetoxyl-5,7-diene androstane-17-ketone intermediate, and hydrolyzing to reduce hydroxyl; constructing a 5alpha, 8alpha-peroxide bridge by illuminating; reacting with hydrazine hydrate to prepare 3beta-hydroxyl-5alpha, 8alpha-peroxy-androstane-6-alkene-17-hydrazine intermediate; and finally performing a condensation reaction to generate the 3beta-hydroxyl-5alpha,8alpha-peroxy-androstane-6-alkene-17-(isatin substituted) hydrazone derivative. The compound has an effect of preventing and treating cancers such as liver cancer, breast cancer and the like.

Synthesis and biological evaluation of novel steroidal 5α,8α-endoperoxide derivatives with aliphatic side-chain as potential anticancer agents

By inspiration of significant anti-cancer activity of our previously screened natural ergosterol peroxide (EP), a series of novel steroidal 5α,8α-endoperoxide derivatives 5a–d and 14a–f were designed, synthesized, and biologically evaluated for their in vitro anti-proliferative inhibitory and cytotoxic activity. The results revealed that most of these compounds showed moderate-to-excellent anti-proliferative effects against the tested cancer cell lines (i.e. HepG2, SK-Hep1, MDA-MB-231 and MCF-7). Among them, compound 5b and 14d exhibited preferable inhibitory activities (IC50 of 5b and 14d are 8.07 and 9.50?μM against HepG2, respectively). The structure-activity relationships indicated that incorporation the peroxidic bridge to the steroid scaffolds at C-5 and C-8 positions together with the aliphatic side-chain at the C-17 position would provide synergistic effect for the bioactivity.

Role of microsomal steroid hydroxylases in Δ7-steroid biosynthesis

CYP17 (steroid 17α-hydroxylase/17,20-lyase) is a key enzyme in steroid hormone biosynthesis. It catalyzes two independent reactions at the same active center and has a unique ability to differentiate Δ4- steroids and Δ5-steroids in the 17,20-lyase reaction. The present work presents a complex experimental analysis of the role of CYP17 in the metabolism of 7-dehydrosteroids. The data indicate the existence of a possible alternative pathway of steroid hormone biosynthesis using 7-dehydrosteroids. The major reaction products of CYP17 catalyzed hydroxylation of 7-dehydropregnenolone have been identified. Catalytic activity of CYP17 from different species with 7-dehydropregnenolone has been estimated. It is shown that CYP21 cannot use Δ5-Δ7 steroids as a substrate.