10538-58-6Relevant articles and documents
Synthesis of 1β-hydroxydeoxycholic acid in H-2 and unlabeled forms
Hayes, Martin A.,Roberts, Ieuan,Gr?nberg, Gunnar,Lv, Kexin,Lin, Baorui,Bergare, Jonas,Elmore, Charles S.
, p. 221 - 229 (2017)
1β–hydroxydeoxycholic acid in unlabeled and stable isotope labeled forms was required for use as a biomarker for Cytochrome P450 3A4/5 activity. A lengthy synthesis was undertaken to deliver the unlabeled compound and in the process, to develop a route to the deuterium labeled compound. The synthesis of the unlabeled compound was completed but in a very low yield. Concurrent with the synthetic approach, a biosynthetic route was pursued and this approach proved to be much more rapid and afforded the compound in both unlabeled and deuterium labeled forms in a 1-step oxidation from deoxycholic acid and [D4]deoxycholic acid, respectively.
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Burckhardt,Reichstein
, p. 821,828 (1942)
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Yamasaki,Kyogoku
, p. 29,31 (1935)
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Spero,McIntosh,Levin
, p. 1907,1910 (1948)
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Design and synthesis of bile acid-based amino sterols as antimicrobial agents
Aher, Nilkanth G.,Pore, Vandana S.,Mishra, Nripendra N.,Shukla, Praveen K.,Gonnade, Rajesh G.
, p. 5411 - 5414 (2009)
New bile acid-based amino sterols were synthesized in good yields from C-3β-oxiranes as key intermediates. These derivatives were evaluated for their in vitro antimicrobial properties against human pathogens. These compounds showed better antibacterial activity as compared to antifungal activity. Compounds 21 and 22 showed comparable antibacterial activity to gentamicin against Staphylococcus aureus with IC50 values of 5.14 and 4.46 μg/mL. This is the first report for the synthesis of C-3β-oxiranes on the steroids having A/B cis ring junction and these oxiranes have been used for the synthesis of amino sterols 17, 18, 21, and 22.
A stereoselective synthesis of the allo-bile acids from the 5β-isomers
Li, Qingjiang,Tochtrop, Gregory P.
supporting information; experimental part, p. 4137 - 4139 (2011/09/19)
The allo-bile acids are a subset of the family of steroidal detergents found in most vertebrates. Because there are no major biological feedstocks for isolation of the allo-bile acids, they must be synthesized from the abundant 5β-reduced isomers. Here we report a general set of methods for the synthesis of allo-bile acids from the corresponding 5-β isomers demarcated by a selective C-3 oxidation, IBX unsaturation, and stereoselective saturation.
