10538-64-4Relevant articles and documents
Efficient lipase-catalyzed preparation of long-chain fatty acid esters of bile acids: Biological activity and synthetic application of the products
Sugai, Takeshi,Takizawa, Masahiro,Bakke, Mikio,Ohtsuka, Yoshikazu,Ohta, Hiromichi
, p. 2059 - 2063 (1996)
A highly regioselective (3-position) and efficient (quantitative yield) acylation of bile acids catalyzed by immobilized Candida antarctica lipase was established. Methyl cholate derivatives acylated with long-chain fatty acids (C12-C16) showed an inhibitory effect on the growth of some strains of Gram-positive and -negative bacteria (27-400 μg/ml). The anti-bacterial activity was slightly weaker than has been observed for methyl cholate, while the increased lipophilicity and lower melting points of the present derivatives are well suited for a potential germicide which would be safe and be topically applied. This enzyme-catalyzed transesterification is also demonstrated as an expeditious route to ursodeoxycholic acid, in respect of the regioselective introduction of acyl protecting groups on the hydroxyl groups of the intermediates. 7-Ketolithocholic acid, a known direct precursor of ursodeoxycholic acid, was obtained from cholic acid via chenodeoxycholic acid in a 46% yield and 9 steps.
Synthesis of Amino analogues of cholic acid
Maslov,Morozova,Solomatina,Shaforostova,Serebrennikova
, p. 507 - 515 (2011)
Amino analogues of cholic acid were synthesized by reduction of oximes using titanium(III) chloride in the presence of sodium cyanoborohydride. Pleiades Publishing, Ltd., 2011.
Synthesis, NMR Characterization and Crystal Structure of Methyl 3α,7α-Dihydroxy-12-oxo-5β-cholanate
Tinajero-Delgado, Vernica,Romero-vila, Margarita,Flores-lamo, Marcos,Arteaga, Martn A. Iglesias
, p. 487 - 492 (2014)
The crystal structure and NMR characterization of methyl 3α,7α-dihydroxy-12-oxo-5β-cholanate are described. The title compound which was obtained from methyl cholanate in a 3-step synthetic sequence that does not alter the starting chirality, crystallizes in the monoclinic system with P 21 space group. While despite the substitution pattern rings A, B and C adopt chair conformations, the 5 membered D ring, that bears the side chain attached to C-17, shows a twisted conformation on C-13-C-14. In the crystal array, classical hydrogen bond interactions O-H···H and intermolecular contacts C-H···O of hydrogen bond type are observed. Graphical Abstract: The crystal structure and NMR characterization of Methyl α,7α-dihydroxy-12-oxo-5β-cholanate are described. [Figure not available: see fulltext.]
