1693-63-6

Usage

Uses

Used in Pharmaceutical Industry:
21-Hydroxypregnenolone 3,21-diacetate is used as an intermediate in the synthesis of Sodium 3-hydroxy-androst-5-ene-17-methylsulfate (S333300), a derivative of the pheromone Androstenone. 21-HYDROXYPREGNENOLONE 3,21-DIACETATE has potential applications in the development of pharmaceuticals targeting androgen-related conditions and disorders.
Used in Research Applications:
21-Hydroxypregnenolone 3,21-diacetate is used as a research compound for studying the effects of androgens on various biological processes. It can be employed in experiments to investigate the role of androgens in cell growth, differentiation, and other physiological functions.

InChI:InChI=1/C25H36O5/c1-15(26)29-14-23(28)22-8-7-20-19-6-5-17-13-18(30-16(2)27)9-11-24(17,3)21(19)10-12-25(20,22)4/h5,18-22H,6-14H2,1-4H3

Upstream product

• 1778-02-5 Pregnenolone acetate 
• 108-24-7 acetic anhydride 
• 20576-31-2 21-bromo-3β-hydroxy-5-pregnen-20-one 3-acetate 
• 124-41-4 sodium methylate 
• 82806-32-4 3β-hydroxy-17β-(nitromethyl)-androst-5-ene 
• 82806-34-6 (3S,8S,9S,10R,13S,14S,17S)-17-(2-Hydroxy-1-nitro-ethyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 1164-98-3 21-hydroxypregnenolone 
• 103188-84-7 3β-acetoxy-20,20-ethanediyldioxy-21-bromo-pregn-5-ene 
• 40148-10-5 (3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,3,4,7, 8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 
• 87680-60-2 3β-hydroxy-17-(nitromethylidene)-androst-5-ene 
• 53-43-0 dehydroepiandrosterone 
• 104203-43-2 21-Benzoyloxy-3β-hydroxy-5-pregnen-20-on 
• 19637-35-5 3-tetrahydropyran-2-yloxy-androst-5-en-17-one 
• 81477-85-2 methyl 20ξ-methoxy-3β-(tetrahydropyranyloxy)-5,17(20)-pregnadien-21-oate 

Downstream Products

• 40129-02-0 3β,21-diacetoxy-5α-pregnan-20-one 
• 86416-32-2 3β,21-dihydroxy-9β,10α-pregna-5,7-dien-20-one 
• 1263386-09-9 C₂₁H₃₀O₅ 
• 860616-06-4 (5Z,7E)-3β,21-dihydroxy-9,10-secopregna-5,7,10(19)-trien-20-one 
• 1164-98-3 21-hydroxypregnenolone 
• 436802-18-5 3β-acetoxy-17β-[2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl]androst-5-ene 
• 436802-12-9 3β-acetoxy-17β-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-ene 
• 436802-05-0 17β-[2-(4-nitrophenyl)-4,5-dihydrooxazol-4-yl]androst-5-en-3β-ol 
• 436802-07-2 17β-[2-(4-methoxyphenyl)-4,5-dihydrooxazol-4-yl]androst-5-en-3β-ol 
• 436801-87-5 17β-[2-(4-bromophenyl)-4,5-dihydrooxazol-4-yl]androst-5-en-3β-ol 
• 6626-60-4 NSC 58246 
• 23330-61-2 3β-acetoxy-14α-carda-5,20(22)-dienolide 
• 76986-11-3 3β-acetoxy-20ξ-hydroxy-5-cardenolide 
• 1207630-74-7 (5'R)-3β-acetoxy-17β-[2-(2-chlorophenyl)-phenyl-4,5-dihydrooxazol-5-yl]androst-5-ene 

Relevant academic research and scientific papers

A Simple Construction of the Hydroxy-ketone Side Chain of Corticosteroids from 17-Oxo-steroids via Nitro-olefins

17-Oxo-steroids, in the presence of catalytic amounts of ethylenediamine, react smoothly with nitromethane to give the corresponding nitro-olefins; these are easily transformed into 21-hydroxy-20-oxo-corticosteroids with or without a double bond at position 16.

Synthesis of 21-hydroxy-11,19-oxidopregn-4-ene-3,20-dione and 21-hydroxy-6,19-oxidopregn-4-ene-3,20-dione.

The 21-hydroxy analogues of 11,19-oxidoprogesterone and 6,19-oxidoprogesterone have been synthesized from readily available materials. Hydroxylation at C-21 was effected with iodosobenzene (from phenyliodosodiacetate and methanolic potassium hydroxide) on a 20-ketopregnane. For the 11,19-oxido derivative, the hydroxylation was carried out on a precursor containing the oxido-bridge. This approach was not adequate for the 6,19-oxido steroid due to the very low yields encountered; hence in the latter case the order of introduction of the C-21 functionality and the oxido-bridge was reversed.

Design and synthesis of D-ring steroidal isoxazolines and oxazolines as potential antiproliferative agents against LNCaP, PC-3 and DU-145 cells (Dedicated to Prof. Mushtaq A. Qureishi for his pioneering contribution to Natural Product Research at University of Kashmir)

Two series of novel steroidal isoxazolines and oxazolines were synthesized through different routes from dehydroepiandrosterone acetate and pregnenolone acetate, respectively. The synthesis of the analogs of both series is multistep and proceeds in good overall yields. While the key step in the synthesis of former is the cycloaddition of aromatic nitrile oxides across α,β-unsaturated olefins, it is the condensation of α,β-azidoalcohols with aromatic aldehydes in the later. Compounds of both the series were tested for their cytotoxic activities against LNCaP, PC-3 and DU-145 prostate cancer cell lines. Amongst all the compounds of both the series screened for their prostate cancer activity, compound 6a, 6e and 12a are the most active especially against LNCaP and DU-145 cancer cell lines.2014 Elsevier Inc. All rights reserved.

Synthesis and photochemical transformation of 3β,21-dihydroxypregna-5, 7-dien-20-one to novel secosteroids that show anti-melanoma activity

We have synthesized 3β,21-dihydroxypregna-5,7-dien-20-one (21(OH) 7DHP) and used UVB radiation to induce its photoconversion to analogues of vitamin D (pD), lumisterol (pL) and tachysterol (pT). The number and character of the products and the dynamics of the process were dependent on the UVB dose. The main products: pD and pT compounds were characterized by UV absorption, MS and NMR spectroscopy after RP-HPLC chromatography. In addition, formation of multiple oxidized derivatives of the primary products was detected and one of these derivatives was characterized as oxidized 21-hydroxyisotachysterol compound (21(OH)oxy-piT). These newly synthesized compounds inhibited growth of human melanoma cells in a dose dependent manner, with greater or equal potency to calcitriol. 3β,21-Dihydroxy-9β,10α-pregna-5,7-dien-20-one (21(OH)pL) and 21(OH)oxy-piT had higher potency against pigmented melanoma cells, while the EC50 for compounds 21(OH)7DHP and (5Z,7E)-3β,21-dihydroxy-9,10-secopregna-5,7,10(19)-trien-20-one (21(OH)pD) were similar in both pigmented and non-pigmented cells. Moreover, 21(OH)7DHP and its derivatives inhibited proliferation of human epidermal HaCaT keratinocytes, albeit at a lower activity compared to melanoma cells. Importantly, 21(OH)7DHP derivatives strongly inhibited the colony formation of human melanoma cells with 21(OH)pD being the most potent. The potential mechanism of action of newly synthesized compounds was similar to that mediated by 1,25(OH)2D 3 and involved ligand-induced translocation of vitamin D receptor into the nucleus. In summary, we have characterized for the first time products of UVB-induced conversion of 21(OH)7DHP and documented that these compounds have selective, inhibitory effects on melanoma cells.

A new steroidal 5,7-diene derivative, 3β-hydroxyandrosta-5,7-diene-17β-carboxylic acid, shows potent anti-proliferative activity

The new steroidal 5,7-diene, 3β-hydroxyandrosta-5,7-diene-17β-carboxylic acid (17-COOH-7DA), was synthesized from 21-acetoxypregnenolone, with the oxidative cleavage of the side chain being dependent on the presence of oxygen. In human epidermal (HaCaT) keratinocytes, 17-COOH-7DA inhibited proliferation in a dose-dependent manner, starting at a dose as low as 10-11 M. This inhibition was accompanied by decreased expression of epidermal growth factor receptor, bcl2 and cyclin E2 mRNAs and by increased expression of involucrin mRNA. Inhibition of proliferation was associated with slowing of the cell cycle in G1/G0 phases but not with cell death. 17-COOH-7DA was significantly more potent than pregnenolone, 17-COOH-pregnenolone, 17-COOCH3-7DA and calcitriol. 17-COOH-7DA also inhibited proliferation of normal human epidermal melanocytes and human and hamster melanoma lines, however, with lower potency than for keratinocytes. In normal human dermal fibroblasts 17-COOH-7DA stimulated proliferation in serum-free media but inhibited it in the presence of 5% serum. 17-COOH-7DA inhibited cell colony formation of human and hamster melanoma cells, and induced monocyte-like differentiation of human HL60 leukemia cells. Thus, the new steroidal 5,7-diene, 17-COOH-7DA, can serve as an inhibitor of proliferation of normal keratinocytes and normal and malignant melanocytes, as a condition-dependent regulator of fibroblast proliferation and a stimulator of leukemia cell differentiation.

Steroselective synthesis of some steroidal oxazolines, as novel potential inhibitors of 17α-hydroxylase-C17,20-lyase

17β-Oxazolinyl steroids 7a-g and 8a-g were synthesized. The Lewis acid-catalysed reactions of (20R)-3β-acetoxy-21-azidomethyl-20-hydroxypregn-5-ene with substituted aromatic aldehydes led to the formation of 3β-acetoxyandrost-5-enes substituted in positio

Neighboring group participation. Part 17 Stereoselective synthesis of some steroidal 2-oxazolidones, as novel potential inhibitors of 17α-hydroxylase-C17,20-lyase

During the alkaline methanolysis of 3β-acetoxy-21-chloropregn-5-ene-20β-N-phenylurethane (4a), and its 4-monosubstituted (4b-e) and 3,5-disubstituted (4f) phenyl derivatives, cyclization occurs, in the course of which 17β-[3-(N-phenyl)-2-oxazolidon-5-yl]androst-5-en-3β-ol (5a) and its substituted phenyl derivatives (5b-f) are formed. The cyclization takes place with (N--5) neighboring group participation. The reaction of 3β-acetoxy-21-azidopregn-5-en-20β-ol (3d) with triphenylphosphine gave 3β-acetoxy-21-phosphiniminopregn-5-en-20β-ol, which reacted in situ with carbon dioxide with the participation of the sterically favored 20β-OH to give the unsubstituted steroidal cyclic carbamate (8). Oppenauer oxidation of the 3β-hydroxy-exo-heterocyclic steroids (5a-f, 9) yielded the corresponding Δ4-3-ketosteroids (7a-f, 10). The inhibitory effects (IC50) of these compounds on rat testicular C17,20-lyase were investigated with an in vitro radioligand incubation technique. The N-unsubstituted 17β-(2-oxazolidon-5-yl)-androst-4-en-3-one derivative (10) was found to be a potent inhibitor (IC50 = 3.0 μM).

Synthesis of some steroidal oxazolines

Steroidal oxazolines 4a-4d and 5a-5f were synthesized. The acid-catalyzed reactions of 21-azido-20-hydroxy- and 21-hydroxy-20-azidosteroids with substituted aromatic aldehydes led to the formation of androst-5-en-3β-ols substituted in position 17β with oxazoline residues.

Novel 20 benzcylamino pregnene derivatives and process for preparing same

The invention relates to new pregnene derivatives of the general formula (I), STR1 wherein R1 stands for a C1-4 alkyl group; R2 stands for a hydrogen atom or a C2-4 alkanoyl group; R3 stands for a hydrogen atom, a hydroxyl group or a C2-4 alkanoyloxy group; A represents a ring of the general formula (1) STR2 or a ring of the general formula (2), STR3 wherein R4 means a hydrogen atom or a methyl group; R5 stands for a hydroxyl group, a C2-4 alkanoyloxy group or a C1-3 alkoxy group; R6 means a hydroxyl group, a C2-4 alkanoyloxy group, a C1-3 alkoxy group, an oxo group or a C2-3 alkylenedithio group; the dotted line optionally represents one or more additional valence bonds, with the proviso that, when the dotted line between C9 and C11 represents an additional valence bond, then R3 stands for a hydrogen atom; and the wavy line shows that the given substituent can be bound to the carbon atom in two alternative spatial arrangements, as well as to their stereoisomers and the mixture of these stereoisomers. The compounds of the general formula (I) are valuable intermediates for the synthesis of known biologically active 21-hydroxyprogesterone derivatives.

New Synthesis of the Corticosterone Side-Chain

Condensation reactions between azlactone 2 and 17-ketosteroids 1 followed by opening of the azlactone ring with sodium methanolate yields methyl 20-benzoylamino-17(20)-pregnen-21-oates 6.Reduction of the ester and subsequent hydrolysis produce compounds with the corticosterone side-chain as well as a ring-closed product of new type.