2205-86-9

Upstream product

• 5490-69-7 5α-bromo-6β,19-epoxypregnan-3,20-dione 
• 2723-07-1 5-Bromo-6β-hydroxy-20-oxo-5α-pregnan-3β-yl acetate 
• 5563-20-2 3β-hydroxy-5-bromo-6β,19-epoxy-5α-pregnan-20-one 
• 41767-48-0 5-Bromo-20-oxo-6β,19-epoxy-5α-pregnan-3β-yl acetate 
• 1778-02-5 Pregnenolone acetate 
• 145-13-1 Pregnenolone 

Downstream Products

• 596-63-4 19-Hydroxyprogesterone 
• 974-38-9 19-Oxo-progesteron 

Relevant academic research and scientific papers

Synthesis of 19-hydroxypregn-4-en-20-one and 19-hydroxy-5β-pregn-3-en-20-one that selectively bind to membrane progesterone receptors, and assessment of their immunomodulatory effects

A new approach to the synthesis of isomeric 19-hydroxypregn-4-en-20-one (1) and 19-hydroxy-5β-pregn-3-en-20-one (2), the selective ligands of membrane progesterone receptors, in a ratio of 1.5:1 is presented. The effect of these steroids on the gene expression of several cytokines (TNFα, IL-1β, IL-6, and TGFβ) in K562 cells was studied. Progesterone and compound 1 acted unidirectionally, significantly decreasing the TGFβ mRNA levels in these cells. The highest activity was exhibited by compound 2 which regulated the expression of the three studied genes, increasing the level of TNFα mRNA and IL-1β mRNA and decreasing the level of TGFβ mRNA. The immunomodulatory effect of the synthesized selective ligands of membrane progesterone receptors found in K562 cells is comparable (for 1) or even surpasses (for 2) the effect of a natural hormone.

SYNTHESIS OF 19-HYDROXYSTEROIDS II. NEW SYNTHESIS OF 19-HYDROXYPROGESTERONE

19-Hydroxyprogesterone has been synthesized in seven stages from pregnenolone with an overall yield of 11percent.