1819-14-3

Upstream product

• 81968-78-7 3β-hydroxy-5,7-pregnadien-20-one 
• 1778-02-5 Pregnenolone acetate 
• 28319-79-1 pregna-5,7-diene-3β-ol-20-one acetate 

Relevant academic research and scientific papers

Method for synthesizing dydrogesterone

The invention relates to a method for synthesizing a steroid drug dydrogesterone (CAS: 152-62-5). The method comprises the following steps: starting from pregnenolone, carrying out allylic halogenation and elimination to obtain a Pregna-5, 7-dien-3-ol-20-one intermediate; carrying out illumination isomerization to obtain a key intermediate 9 beta, 10 alpha-Pregna-5, 7-dien-3-ol-20-one; then carrying out Oppenauer oxidation (Oppenauer oxidation) to obtain 7-Dehydro-9beta, 10 alpha-progesterone, and finally, carrying out olefin shift isomerization under the action of acid to obtain the final product 6-Dehydro-9beta, 10 alpha-progesterone (a crude drug of dydrogesterone). The method is economical in steps and comprises four conversion steps; the total yield is as high as 16.4%; the raw materials are cheap and easy to obtain, the whole process route is green and safe, the bulk drugs are high in quality, the purity can reach 99.5% or above, and the method is suitable for industrial production.

Method and compound for synthetizing reprogestin

To the synthesis method, dehydropregnenolone is taken as a starting material, carbonyl-protected dehydropregnenolone is prepared, and then a methyl configuration overturning compound is obtained through photo-catalytic reaction and further subjected to deprotection. Hydroxylation and double bond rearrangement reaction yield progestin. The method has the advantages of easily available raw materials, high yield and simple and mild reaction conditions, and is suitable for industrial production of progestin.

Preparation method of dydrogesterone intermediate

The invention discloses a preparation method of a dydrogesterone intermediate. The preparation method is characterized by comprising the following steps: dissolving 5,7-diene steroid compound in an organic solvent to obtain a solution as a raw material; and carrying out a photocatalytic reaction and separating to obtain the dydrogesterone intermediate, wherein the 5,7-diene steroid compound is 7-dehydropregnenolone acetate, pregna-5,7-diene-3,20-diketodivinyl ketal, 7-dehydropregnenolone, ergosterol or pregna-5,7-diene-3,20-diketo-3-vinyl ketal, and a lamp used in the photocatalytic reaction comprises an LED ultraviolet lamp with the wavelength range of 295-335 nm. The preparation method of the dydrogesterone intermediate is high in yield, low in cost, safer in preparation and friendlier to environment.

Lumisterol is metabolized by CYP11A1: Discovery of a new pathway

Lumisterol3 (L3) is produced by photochemical transformation of 7-dehydrocholesterol (7-DHC) during exposure to high doses of ultraviolet B radiation. It has been assumed that L3 is biologically inactive and is not metabolized in the body. However, some synthetic derivatives of L3 display biological activity. The aim of this study was to test the ability of CYP11A1 to metabolize L3. Incubation of L3 with bovine or human CYP11A1 resulted in the formation of three major and a number of minor products. The catalytic efficiency of bovine CYP11A1 for metabolism of L3 dissolved in 2-hydroxypropyl-β-cyclodextrin was approximately 20% of that reported for vitamin D3 and cholesterol. The structures of the three major products were identified as 24-hydroxy-L3, 22-hydroxy-L3 and 20,22-dihydroxy-L3 by NMR. 22-Hydroxy-L3 was further metabolized by bovine CYP11A1 to 20,22-dihydroxy-L3. Both 22-hydroxy-L3 and 20,22-dihydroxy-L3 gave rise to a minor metabolite identified from authentic standard and mass spectrometry as pregnalumisterol (pL) (product of C20-C22 side chain cleavage of L3) and two trihydroxy-L3 products. The capability of tissues expressing CYP11A1 to metabolize L3 was demonstrated using pig adrenal fragments where 20,22-dihydroxy-L3, 22-hydroxy-L3, 24-hydroxy-L3 and pL were detected by LC/MS. Thus, we have established that L3 is metabolized by CYP11A1 to 22- and 24-hydroxy-L3 and 20,22-dihydroxy-L3 as major products, as well as to pL and other minor products. The previously reported biological activity of pL and the presence of CYP11A1 in skin suggest that this pathway may serve to produce biologically active products from L3, emphasizing a novel role of CYP11A1 in sterol metabolism.