7753-75-5Relevant academic research and scientific papers
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 (2017/04/10)
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.
Deoxycholic acid derivatives as inhibitors of P-glycoprotein-mediated multidrug efflux
Rocheblave, Luc,de Ravel, Marc Rolland,Monniot, Elodie,Tavenard, Jeremy,Cuilleron, Claude-Yves,Grenot, Catherine,Radix, Sylvie,Matera, Eva-Laure,Dumontet, Charles,Walchshofer, Nadia
, p. 5 - 12 (2016/10/09)
Deoxycholic acid derivatives were designed as P-glycoprotein (Pgp, ABCB1) inhibitors. Thus the synthesis and the biological activity of methyl deoxycholate derivatives 5–10 and their ether analogs 15–20 have been reported. The potency of these compounds to modulate Pgp-mediated MDR was evaluated through daunorubicin accumulation and potentiation of doxorubicin cytotoxicity in K562/R7 multidrug resistant cells overexpressing Pgp. In parallel, their intrinsic toxicity was appreciated on K562 sensitive cells. Methyl 12α-[(2R or 2S) tetrahydro-2H-pyran-2-yloxy]-3-oxo-5β-cholan-24-oate 9b has shown a good efficiency as a Pgp inhibitor and a low intrinsic toxicity. Therefore, this derivative constitutes a new lead compound which can be used as a starting point to improve the design of non-toxic Pgp modulators.
Partial synthesis of a marine secosterol from Gersemia fruticosa: Preparation of the intermediate precursor 3β,6α-diacetoxy-24-methyl-12-oxo-5α-chol-9,11-en-24-oate
Kuhl, Alexander,Kreiser, Wolfgang
, p. 1145 - 1148 (2007/10/03)
The conversion of desoxycholic acid (2) into the title compound 14 by 13 respectively 17 steps is described herein, including stereoselective construction of C-3 and C-6 hydroxy moieties and introduction of a Δ9,11 double bond by dehydrogenation. 14 is believed to serve as a putative precursor for the synthesis of secosterol 1, isolated from the soft coral Gersemia fruticosa.
An efficient synthesis of 4β and 6α-hydroxylated bile acids
Yoshimura, Teruki,Mahara, Reijiro,Kurosawa, Takao,Ikegawa, Shigeo,Tohma, Masahiko
, p. 52 - 58 (2007/10/02)
An efficient method for the preparation of 4β- and 6α-hydroxylated bile acids has been developed.It involved a highly stereoselective acetoxylation at the 4β and 6α positions of 3- and 7-oxo bile acids, respectively, with lead tetraacetate in the presence of boron trifluoride etherate in acetic acid.Reduction of the resulting α-acetoxy ketones with sodium borohydride or tert-butylamine borane complex, and alkaline hydrolysis, provided the desired bile acids in good yields. Keywords: sterols; bile acid; 4β-hydroxylated bile acid;6α-hydroxylated bile acid; acetoxylation; lead tetraacetate oxidation
Direct transformation of steroidal ethers into ketones by dimethyldioxirane
Van Heerden,Dixon,Holzapfel
, p. 7399 - 7402 (2007/10/02)
Treatment of the methyl- and benzyl ethers of 3-hydroxy steroids with a solution of dimethyldioxirane resulted in the formation of the corresponding ketones in high yield.
