1297604-02-4

Basic information

• Product Name: N-[(3β,18β,20β)-3-(acetoxy)-11-oxo-30-norolean-12-en-20-yl]-N'-(phenylmethyl)urea
• Synonyms: N-[(3β,18β,20β)-3-(acetoxy)-11-oxo-30-norolean-12-en-20-yl]-N'-(phenylmethyl)urea
• CAS NO: 1297604-02-4
• Molecular Weight: 616.885
• Mol File: 1297604-02-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-[(3β,18β,20β)-3-(acetoxy)-11-oxo-30-norolean-12-en-20-yl]-N'-(phenylmethyl)urea(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(3β,18β,20β)-3-(acetoxy)-11-oxo-30-norolean-12-en-20-yl]-N'-(phenylmethyl)urea(1297604-02-4)
• EPA Substance Registry System: N-[(3β,18β,20β)-3-(acetoxy)-11-oxo-30-norolean-12-en-20-yl]-N'-(phenylmethyl)urea(1297604-02-4)

Safety Data

• Hazardous Substances Data: 1297604-02-4(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 30244-17-8 (3β,18β,20β)-3-(acetoxy)-20-isocyanato-30-norolean-12-en-11-one 
• 58307-68-9 Acetic acid (3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-azidocarbonyl-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-yl ester 
• 30151-31-6 3β-acetoxy-11-oxo-18β-olean-12-en-30-oyl chloride 
• 471-53-4 enoxolone 

Relevant articles and documents

Synthesis of new glycyrrhetinic acid derived ring A azepanone, 29-urea and 29-hydroxamic acid derivatives as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors

Glycyrrhetinic acid, the metabolite of the natural product glycyrrhizin, is a well known nonselective inhibitor of 11β-hydroxysteroid dehydrogenase (11β-HSD) type 1 and type 2. Whereas inhibition of 11β-HSD1 is currently under consideration for treatment of metabolic diseases, such as obesity and diabetes, 11β-HSD2 inhibitors may find therapeutic applications in chronic inflammatory diseases and certain forms of cancer. Recently, we published a series of hydroxamic acid derivatives of glycyrrhetinic acid showing high selectivity for 11β-HSD2. The most potent and selective compound is active against human 11β-HSD2 in the low nanomolar range with a 350-fold selectivity over human 11β-HSD1. Starting from the lead compounds glycyrrhetinic acid and the hydroxamic acid derivatives, novel triterpene type derivatives were synthesized and analyzed for their biological activity against overexpressed human 11β-HSD1 and 11β-HSD2 in cell lysates. Here we describe novel 29-urea- and 29-hydroxamic acid derivatives of glycyrrhetinic acid as well as derivatives with the Beckman rearrangement of the 3-oxime to a seven-membered ring, and the rearrangement of the C-ring from 11-keto-12-ene to 12-keto-9(11)-ene. The combination of modifications on different positions led to compounds comprising further improved selective inhibition of 11β-HSD2 in the lower nanomolar range with up to 3600-fold selectivity.

GLYCYRRHETINIC ACID AMINE ANALOGUES FOR USE IN THE TREATMENT OF INFLAMMATION, INFECTIOUS DISEASES, CANCER, AUTOIMMUNE DISEASES, SKIN DISEASES, BONE DISEASES AND METABOLIC DISEASES

The present invention encompasses compounds of general formula (I) wherein R3a to R31 and X are defined as in claim 1, which are suitable for the treatment of and/or prevention of chronic inflammatory diseases, autoimmune diseases, skin diseases, bone diseases, metabolic diseases, infectious diseases and cancer.