- Efficient lipase-catalyzed preparation of long-chain fatty acid esters of bile acids: Biological activity and synthetic application of the products
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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.
- Sugai, Takeshi,Takizawa, Masahiro,Bakke, Mikio,Ohtsuka, Yoshikazu,Ohta, Hiromichi
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- Synthesis of cholic acid amino analogues by oxime reduction with TiCl 3-NaBH3CN
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Amino analogues of cholic acid have been synthesized by reduction of the corresponding oximes with titanium(iii) chloride in the presence of sodium cyanoborohydride.
- Maslov, Mikhail A.,Morozova, Nina G.,Solomatina, Tatyana V.,Sergeeva, Olga A.,Cheshkov, Dmitry A.,Serebrennikova, Galina A.
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- Synthesis of Amino analogues of cholic acid
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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.
- Maslov,Morozova,Solomatina,Shaforostova,Serebrennikova
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- Synthesis, NMR Characterization and Crystal Structure of Methyl 3α,7α-Dihydroxy-12-oxo-5β-cholanate
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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.]
- Tinajero-Delgado, Vernica,Romero-vila, Margarita,Flores-lamo, Marcos,Arteaga, Martn A. Iglesias
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- Chenodeoxycholic acid derivative or pharmaceutically acceptable salt thereof, and preparation method and applications thereof
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The invention discloses a chenodeoxycholic acid derivative with a structure as shown in general formula I or a medicinal salt thereof, and a preparation method and application of the chenodeoxycholicacid derivative. The chenodeoxycholic acid derivative can up-regulate the transcription levels of FXR mRNA and SHP mRNA, can obviously activate FXR, and can be used for preparing drugs for treating orpreventing hyperlipidemia, atherosclerosis, non-alcoholic steatohepatitis, type II diabetes mellitus and other diseases related to blood fat.
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Paragraph 0051; 0052; 0053
(2020/03/12)
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