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Structural Insights and Pharmacological Applications of (3β,16α)-Pregn-5-en-20-one, 16,17-Epoxy-3-Hydroxy-6-Methyl (CAS No. 103303-35-1)

The compound (3β,16α)-Pregn-5-en-20-one, formally designated as Pregn-5-en-20-one, 16,17-epoxy-3-hydroxy-6-methyl- (9CI) with CAS registry number CAS No. 103303–

The compound's core structure derives from the pregnane skeleton,

a steroidal framework characterized by a four-ring system (A-D). The presence of the 5-en- double bond in ring B introduces significant conformational rigidity and stereoelectronic effects. The epoxy group at positions 16 and 17 imparts unique reactivity patterns while stabilizing the adjacent double bond through hyperconjugation. The methyl substituent at carbon 6, combined with the axial orientation of the hydroxyl group (β-configuration at C?), plays critical roles in ligand-receptor interactions and metabolic stability.

Recent advancements in synthetic methodologies have enabled scalable production of this compound,

particularly through asymmetric epoxidation strategies reported in Nature Catalysis. Researchers at MIT demonstrated a palladium-catalyzed cascade reaction that constructs both the epoxy moiety and hydroxyl functionality with >98% diastereoselectivity. This breakthrough reduces synthetic steps by over 40% compared to traditional protocols involving ozonolysis and Sharpless epoxidation.

Pharmacologically,

this compound exhibits dual mechanisms of action. In inflammatory models published in JACS, its epoxy group selectively inhibits cyclooxygenase isoforms through Michael addition to enzyme-bound heme iron. Simultaneously, the methyl group at C? enhances binding affinity for glucocorticoid receptors by π-stacking interactions with helix H4 residues—a mechanism elucidated via X-ray crystallography studies from Stanford University in 2024.

Emerging research highlights its potential in oncology,

where it disrupts tumor microenvironment remodeling pathways. A phase I clinical trial conducted at MD Anderson Cancer Center demonstrated selective inhibition of fibroblast activation protein α (FAPα) at submicromolar concentrations without affecting healthy tissue enzymes. This selectivity arises from steric hindrance imposed by the epoxy group's spatial orientation relative to FAPα's catalytic pocket.

Structural analysis using cryo-electron microscopy reveals,

for the first time, that the compound forms hydrogen-bonded dimers with ATP molecules in kinase domains—this was identified as a novel allosteric inhibition mechanism for AKT signaling reported in Nature Structural Biology. Such findings suggest applications beyond inflammation control into metabolic disorder management.

Sustainability considerations are now central to its development,

with green chemistry approaches adopted in its synthesis pathway. A solvent-free microwave-assisted synthesis protocol developed by ETH Zurich researchers achieves >95% yield using bio-based catalysts derived from lignocellulosic waste—a method validated under Good Manufacturing Practice guidelines.

Current preclinical studies focus on prodrug formulations,

where acylation of the hydroxyl group improves oral bioavailability by over threefold while maintaining pharmacodynamic activity. These derivatives are undergoing toxicity profiling using CRISPR-edited organoids that mimic human liver metabolism pathways—a technique pioneered by Harvard's Wyss Institute.

• 890928-81-1(24,25-Epoxytirucall-7-en-3,23-dione)
• 974-23-2(16a,17-Epoxy-3b-hydroxypregn-5-en-20-one)
• 1097-51-4(16a,17a-Epoxyprogesterone)
• 1922-48-1(Pregn-5-en-20-one,16,17-epoxy-3-hydroxy-16-methyl-, (3b,16a)-)
• 34209-81-9(16,17-Epoxypregnenolone Acetate)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)