1162-54-5

Basic information

• Product Name: 1,4-PREGNADIEN-3,20-DIONE
• Synonyms: PREGNA-1,4-DIENE-3,20-DIONE;1-DEHYDROPROGESTERONE;1,4-PREGNADIEN-3,20-DIONE;DELTA1-PROGESTERONE
• CAS NO: 1162-54-5
• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.45
• Mol File: 1162-54-5.mol

Chemical Properties

• Melting Point: 151-152 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 449.2°Cat760mmHg
• Flash Point: 167.4°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 2.91E-08mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 1,4-PREGNADIEN-3,20-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-PREGNADIEN-3,20-DIONE(1162-54-5)
• EPA Substance Registry System: 1,4-PREGNADIEN-3,20-DIONE(1162-54-5)

Safety Data

• Hazardous Substances Data: 1162-54-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,4-PREGNADIEN-3,20-DIONE is used as an intermediate in the synthesis of cytotoxic agents with steroidal derivatives for the development of anti-cancer drugs. Its unique chemical structure allows for the creation of potent compounds that can target and eliminate cancer cells.
Used in Antiviral Applications:
1,4-PREGNADIEN-3,20-DIONE is used as an anti-flu virus agent due to its ability to inhibit the replication of influenza viruses. This application can be particularly useful in the development of new antiviral medications to combat seasonal and pandemic flu strains.

InChI:InChI=1/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h8,10,12,16-19H,4-7,9,11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1

Upstream product

• 57-83-0 Progesterone 
• 10163-72-1 20β_F-hydroxy-pregna-1,4-dien-3-one 
• 901-57-5 (20R)-pregn-5-ene-3β,20-diol 
• 566-66-5 3β-hydroxy-pregn-4-en-20-one 
• 57670-43-6 1β,3β-dihydroxy-pregn-5-en-20-one 
• 566-91-6 cholesta-1,4-dien-3-one 
• 108355-08-4 24-norchol-1,4-dien-3-one 
• 108355-04-0 25-methylcholesta-1,4-dien-3-one 
• 96790-16-8 20-methyl-3-oxopregna-1,4-dien-21-al 
• 35525-27-0 22-hydroxy-23,24-bis-norchola-1,4-diene-3-one 
• 81201-82-3 (20S)-3-oxopregna-1,4-diene-20-carboxaldehyde 
• 71658-22-5 22-hydroxy-23,24-bisnor-1,4-choladien-3-one 
• 89025-55-8 3α-acetoxy-24-nor-5β-cholane 
• 71016-64-3 3α-acetoxy-23-bromo-5β-norcholane 

Downstream Products

• 1667-98-7 3-hydroxy-19-norpregna-1,3,5⁽¹⁰⁾-trien-20-one 
• 5508-55-4 (+)-21-hydroxy-3,20-dioxo-pregna-1,4-diene 
• 57-83-0 Progesterone 
• 77546-81-7 20-amino-3-oxo-pregna-1,4-diene 
• 134332-55-1 20-succinamylpregna-1,4-dien-3-one 
• 134329-82-1 E-1-acetyl-9-<4-hydroxyphenylmethylene>-12a-methyl-8-oxo-5-1,2,3,3a,3b,4,8,9,10b,11,12,12a-dodecahydrocyclopenta<7,8>phenanthro<3,4-b>furan 
• 134329-88-7 E-1-acetyl-9-<4-methoxyphenylmethylene>-12a-methyl-8-oxo-5-1,2,3,3a,3b,4,8,9,10b,11,12,12a-dodecahydrocyclopenta<7,8>phenanthro<3,4-b>furan 
• 1448329-02-9 21E-benzylidenepregn-1,4-diene-3,20-dione 
• 1448329-03-0 21E-(2-chlorobenzylidene)pregn-1,4-diene-3,20-dione 
• 1448329-04-1 21E-(4-chlorobenzylidene)pregn-1,4-diene-3,20-dione 

Relevant articles and documents

Synthesis and cytotoxic activity of some novel steroidal C-17 pyrazolinyl derivatives

Fourteen novel steroidal C-17 pyrazolinyl derivatives 9a-g and 10a-g were synthesized from commercially available progesterone and tested for their cytotoxic activity against brine shrimp (Artemia salina) and three human cancer cell lines (NCI-H460, HeLa, and HepG2). Some of these synthetic compounds exhibited significant cytotoxic activity, and treatment of HeLa cells with compound 10b resulted in the cell population arrest in the S phase. A structure-activity relationship was discussed.

Synthesis of novel 4′-acylamino modified 21E-benzylidene steroidal derivatives and their cytotoxic activities

A series of 4′-acylamino modified Δ1,4-pregnadien-21E-benzylidene-3,20-dione derivatives (6a–v) was synthesized from the commercially available progesterone (1). These title compounds were evaluated for their toxicity against brine shrimp (Arte

ENABLING CHOLESTEROL CATABOLISM IN HUMAN CELLS

Compositions, methods, and systems for modifying sterol metabolism in a subject is disclosed. In some embodiments, the subjects may be administered one or more mammalian cells modified to express at least one sterol degrading enzyme derived from a bacterium. In many embodiments, the cell is a macrophage or monocyte stably expressing three or more enzymes that aid in opening the β ring of cholesterol. The disclosed compositions and methods may be useful in lowering cholesterol levels in a subject in need thereof. In some embodiments, the subject may have a genetic predisposition to atherosclerosis.

Synthesis of steroidal [1,2,4]triazolo[1,5-a]pyrimidines and their antiproliferative activities

— A facile strategy for the synthesis of steroidal [1,2,4]triazolo[1,5-a]pyrimidines 5a-g and 6a-g has been accomplished via a one-pot reaction of steroidal ketones, aromatic aldehydes and 3-amino-1,2,4-triazole in the presence of potassium tert-butoxide in refluxing tert-butanol. All the synthesized heterosteroids were evaluated for in vitro antiproliferative activity against human cancer cells by sulforhodamine B (SRB) assays. The preliminary results showed that compounds 6a and 6e possessed potent antiproliferative activities.

PROCESS FOR PREPARATION OF DYDROGESTERONE

The present invention relates to process for the preparation of dydrogesterone.

Potential insecticidal activity of steroidal U-17 pyrazolinyl derivatives

Agrochemical research, over the last two decades, has resulted in the discovery of chemically novel insecticides, of which steroids-based compounds that mimic the action of hormones have been considered as safe insecticides. In this study, eight steroidal C-17 pyrazolinyl derivatives were resynthesized through molecular hybridization and their insecticidal activities against 4th instar larvae of Mythimna separate were evaluated. These results showed that some compounds exhibited significant insecticidal activities and the susceptibility assays were expressed as the median lethal dose (LD50), of which one of the compounds exerted the most potent insecticidal activity (LD50 = 296 μg g-1), comparable to that of the natural product insecticide, celangulatin V (LD50 = 260 μg g-1). This strategy led to a promising candidate for the development of new steroidal insecticidal agents.

Synthesis and cytotoxicity of some novel 21E-benzylidene steroidal derivatives

A series of novel derivatives of 21E-benzylidene-pregn-1,4-diene-3,20-dione 7a-g and 21E-benzylidene-4-chloro-pregn-1,4-diene-3,20-dione 8a-g was synthesized from the commercially available progesterone. These title compounds were evaluated for their cyto

A practical Δ1-dehydrogenation of Δ4-3-keto-steroids with DDQ in the presence of TBDMSCl at room temperature

A mild and efficient Δ1-dehydrogenation of Δ4-3-keto-steroids with DDQ in the presence of tertbutyldimethylchlorosilane at room temperature was developed.

Novel catalytic activity of immobilized spores under reduced water activity

Onset of a new catalytic function during transformation of progesterone by immobilized spores of Aspergillus ochraceus TS under reduced water activity is reported. The pathway of transformation, which furnished 1,4-androstadien-17β-ol-3-one and 1,4-androstadien-3,17-dione due to cleavage of C17-C20 bond, is different from normal reaction sequence.

Synthesis of [3H2]-21-diazoprogesterone as a potent photoaffinity labelling reagent for the mineralocorticoid receptor

[3H2]-21-Diazoprogesterone ([3H2]21DP), a potent photoaffinity labelling reagent, has been synthesized in four steps from progesterone. Tritium has been introduced by homogeneous tritiation with Wilkinson's catalyst.