1016226-71-3Relevant articles and documents
Novel components of the human metabolome: The identification, characterization and anti-inflammatory activity of two 5-androstene tetrols
Ahlem, Clarence N.,Page, Theodore M.,Auci, Dominick L.,Kennedy, Michael R.,Mangano, Katia,Nicoletti, Ferdinando,Ge, Yu,Huang, Yujin,White, Steven K.,Villegas, Sonia,Conrad, Douglas,Wang, Angela,Reading, Christopher L.,Frincke, James M.
, p. 145 - 155 (2011)
Two natural 5-androstene steroid tetrols, androst-5-ene-3β,7β, 16α,17β-tetrol (HE3177) and androst-5-ene-3α,7β,16α, 17β-tetrol (HE3413), were discovered in human plasma and urine. These compounds had significant aqueous solubility, did not bind or transactivate steroid-binding nuclear hormone receptors, and were not immunosuppressive in murine mixed-lymphocyte studies. Both compounds appear to be metabolic end products, as they were resistant to primary and secondary metabolism. Both were orally bioavailable, and were very well tolerated in a two-week dose-intensive toxicity study in mice. Anti-inflammatory properties were found with exogenous administration of these compounds in rodent disease models of multiple sclerosis, lung injury, chronic prostatitis, and colitis.
METHODS AND COMPOUNDS FOR PREPARING 3ALPHA-OXYGEN SUBSTITUTED STEROIDS
-
, (2012/09/05)
The invention relates to processes for preparing 3α-O-linked steroids including 3α-O-linked-androst-5-ene steroids and 3α-O-linked-5a-androstane steroids. In one process a 3α,4α-epoxy androst-5-en-17-one is predominately reduced at the epoxy moiety wherein reduction of the 3α,4α epoxy functional group occurs preferentially at position C4 with retention of configuration at position C3 to provide a 3α-O-linked-androst-5-ene steroid. In another process, conditions are provided for inversion of configuration of a 3β-hydroxy-androst-5-ene steroid by the Mitsunobu reaction to provide a 3α-O-linked-androst-5-ene steroid with reduced amounts of 3α,5α-cycloandrostane side-product impurities.
