21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione

Names

[ Name ]:
21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione

[Synonym ]:
21-(Acetyloxy)pregna-1,4,9(11),16-tetraene-3,20-dione
EINECS 253-497-3
16-tetraene-3,20-dione 21-acetate
21-hydroxypregna-1,4,9(11)
21-acetoxy-pregna-1,4,9(11),16-tetraene-3,20-dione
3,20-Dioxopregna-1,4,9(11),16-tetraen-21-yl acetate
21-Acetoxy-pregna-1,4,9(11),16-tetraen-3,20-dion
Pregna-1,4,9(11),16-tetraene-3,20-dione, 21-(acetyloxy)-
21-hydroxy-pregna-1,4,9(11),16-tetraene-3,20-dione 21-acetate
2-((8S,10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione

Biological Activity

[Description]:

21-Acetoxypregna-1,4,9(11),16-tetraene-3,20-dione is an intermediate of delta 9,11 steroids synthesis, for example, Vamorolone (HY-109017). The delta 9,11 steroids are modifications of glucocorticoids and has anti-inflammatory properties. The delta 9,11 steroids are agents for protection against cell damage (lipid peroxidation) and inhibition of neovascularization[1].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Research Areas >> Metabolic Disease

Signaling Pathways >> GPCR/G Protein >> Glucocorticoid Receptor

[In Vitro]

Δ9,11 derivatives are designed and developed to stably incorporate into cell membranes and inhibit lipid peroxidation without glucocorticoid or mineralocorticoid activities, thus avoiding side effects associated with traditional corticosteroids[1]. VBP15 acts as a lead compound due to potent NF-κB inhibition and GR translocation similar to prednisone and dexamethasone, lack of transactivation properties, and good bioavailability[1].

[References]

[1]. Erica K M Reeves, et al. VBP15: preclinical characterization of a novel anti-inflammatory delta 9,11 steroid. Bioorg Med Chem

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
534.6±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₃H₂₆O₄

[ Molecular Weight ]:
366.450

[ Flash Point ]:
233.0±30.2 °C

[ Exact Mass ]:
366.183105

[ PSA ]:
60.44000

[ LogP ]:
3.48

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.585

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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