1164-98-3

Usage

Uses

Used in Pharmaceutical Industry:
21-Hydroxypregnenolone is used as a GABAA antagonist for its ability to inhibit the activity of the GABAA receptor, which can have potential therapeutic applications in the treatment of neurological disorders such as epilepsy and anxiety.
Used in Neurological Research:
21-Hydroxypregnenolone is used as a neurosteroid for its role in increasing neurogenesis in the hippocampus, which can have potential applications in the study and treatment of neurodegenerative diseases and cognitive disorders.
Used in Drug Metabolism Studies:
21-Hydroxypregnenolone is used as a modulator of cytochrome P450-3A for its ability to influence the activity of this enzyme, which can have potential applications in the study and development of drugs and their metabolism in the body.

InChI:InChI=1/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h3,14-18,22-23H,4-12H2,1-2H3

Upstream product

• 92588-25-5 [1-((3S,10R,13S,17S)-3-Methoxymethoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-vinyloxy]-trimethyl-silane 
• 566-78-9 21-acetoxypregnenolone 
• 104203-43-2 21-Benzoyloxy-3β-hydroxy-5-pregnen-20-on 
• 14425-92-4 6β-methoxy-3α,5-cyclo-5α-androstan-17-one 
• 19637-35-5 3-tetrahydropyran-2-yloxy-androst-5-en-17-one 
• 1693-63-6 3β,21-diacetoxypregn-5-en-20-one 
• 81477-88-5 6β,20ξ-dimethoxy-17(20)-i-pregnen-21-ol 
• 30460-00-5 21-bromo-3β-hydroxy-5-pregnen-20-one 
• 102544-30-9 3β,21-Dihydroxy-20-ethylmercapto-pregnadien-(5,17(20)) 
• 33769-71-0 21-diazo-3β-hydroxy-pregn-5-en-20-one 
• 3938-96-3 ethyl 2-methoxyacetate 
• 85541-82-8 methyl 5-androsten-3β-ol-17β-carboxylate 
• 23328-05-4 3β-methoxymethoxy-5-pregnen-20-one 
• 145-13-1 pregnenolone 

Downstream Products

• 853-27-0 3,20-dioxo-4-pregnen-21-al 
• 56196-40-8 1-((3S,8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-trimethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-trimethylsilanyloxy-ethanone O-methyl-oxime 
• 1693-63-6 3β,21-diacetoxypregn-5-en-20-one 

Relevant academic research and scientific papers

Hypervalent Iodine in Organic Synthesis. A Novel Route to the Dihydroxyacetone Side-chain in the Pregnene Series

Treatment of pregnenolone (1) with PhI=O and KOH in MeOH yields 3β,21-dihydroxypregn-5-en-20-one dimethyl acetal (2) from which a molecule of MeOH is lost to yield the C(17)-C(20) enol methyl ether (3) which may be epoxidized and hydrolysed to yield the C-17-dihydroxyacetone side-chain in the correct configuration as in 3β,17α,21-trihydroxypregn-5-en-20-one (4).

Resolving entangled jh-h-coupling patterns for steroidal structure determinations by nmr spectroscopy

For decades, high-resolution1H NMR spectroscopy has been routinely utilized to analyze both naturally occurring steroid hormones and synthetic steroids, which play important roles in regulating physiological functions in humans. Because the1H signals are inevitably superimposed and entangled with various JH–H splitting patterns, such that the individual1H chemical shift and associated JH–H coupling identities are hardly resolved. Given this, applications of thess information for elucidating steroidal molecular structures and steroid/ligand interactions at the atomic level were largely restricted. To overcome, we devoted to unraveling the entangled JH–H splitting patterns of two similar steroidal compounds having fully unsaturated protons, i.e., androstanolone and epiandrosterone (denoted as 1 and 2, respectively), in which only hydroxyl and ketone substituents attached to C3 and C17 were interchanged. Here we demonstrated that the JH–H values deduced from 1 and 2 are universal and applicable to other steroids, such as testosterone, 3β, 21-dihydroxygregna5-en-20-one, prednisolone, and estradiol. On the other hand, the1H chemical shifts may deviate substantially from sample to sample. In this communication, we propose a simple but novel scheme for resolving the complicate JH–H splitting patterns and1H chemical shifts, aiming for steroidal structure determinations.

New Preparation and Controlled Alkaline Hydrolysis of 21-Bromo-20-ketopregnenes. A Facile Synthesis of Deoxycorticoids

Syntheses of deoxycorticoids 7b, 8b, and 9b are described.Treatment of 20-oxo steroid 1 with 3 mol equiv of CuBr2 in MeOH in the presence or absence of pyridine gave the 21-bromide 4a or the 17α-methoxide 2 in high yields, respectively.When 6 mol equiv of the brominating reagent was used in the absence of pyridine, the 21-bromo-17α-methoxide 5a was formed. 17α-hydroxy 20-ones 3 could be similarly converted to the 21-bromides 6a and 6b.Oxidation of 4a, 5a, and 6a with CrO3 and subsequent isomerization of a double bond at C-5 with acid gave the corresponding 4-ene-3-ones 7a, 8a, and 9a, of which 7a and 9a were efficiently hydrolized to 7b and 9b under controlled conditions with a K2CO3-H2O-acetone system.On the other hand, 8a was converted to 8b by reaction with NaOCH3 in MeOH.

Effects of fluorine substitution on substrate conversion by cytochromes P450 17A1 and 21A2

Cytochromes P450 17A1 (CYP7A1) and 21A2 (CYP21A2) catalyze key reactions in the production of steroid hormones, including mineralocorticoids, glucocorticoids, and androgens. With the ultimate goal of designing probes that are selectively metabolized to each of these steroid types, fluorinated derivatives of the endogenous substrates, pregnenolone and progesterone, were prepared to study the effects on CYP17A1 and CYP21A2 activity. In the functional assays, the hydroxylase reactions catalysed by each of these enzymes were blocked when fluorine was introduced at the site of metabolism (positions 17 and 21 of the steroid core, respectively). CYP17A1, furthermore, performed the 17,20-lyase reaction on substrates with a fluorine installed at the 21-position. Importantly, none of the substitutions examined herein prevented compound entry into the active sites of either CYP17A1 or CYP21A2 as demonstrated by spectral binding assays. Taken together, the results suggest that fluorine might be used to redirect the metabolic pathways of pregnenolone and progesterone to specific types of steroids.

Novel steroid inhibitors of glucose 6-phosphate dehydrogenase

Novel derivatives of the steroid DHEA 1, a known uncompetitive inhibitor of G6PD, were designed, synthesized, and tested for their ability to inhibit this dehydrogenase enzyme. Several compounds with approximately 10-fold improved potency in an enzyme assay were identified, and this improved activity translated to efficacy in a cellular assay. The SAR for steroid inhibition of G6PD has been substantially developed; the 3β-alcohol can be replaced with 3β-H-bond donors such as sulfamide, sulfonamide, urea, and carbamate. Improved potency was achieved by replacing the androstane nucleus with a pregnane nucleus, provided a ketone at C-20 is present. For pregnan-20-ones incorporation of a 21-hydroxyl group is often beneficial. The novel compounds generally have good physicochemical properties and satisfactory in vitro DMPK parameters. These derivatives may be useful for examining the role of G6PD inhibition in cells and will assist the future design of more potent steroid inhibitors with potential therapeutic utility.

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.

5 α-pregnan-20-ones and 5-pregnen-20-ones and related compounds

Compounds of the formulae: STR1 useful as anti-obesity, anti-diabetic, anti-coronary and hypolipidemic agents.

17-Hydroxy-steroids

Compounds of the formulae: STR1 are useful as anti-cancer, anti-obesity, anti-diabetic, anti-coronary agents, anti-aging agents, anti-hypolipidemic agents and anti-autoimmune agents.

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.

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.