Synthesis of 7- and 12-hydroxy- and 7,12-dihydroxy-3-keto-5β-cholan-24-oic acids by reduction of 3,7-, 3,12- and 3,7,12-oxo derivatives

Fantin, Giancarlo; Fogagnolo, Marco; Medici, Alessandro; Pedrini, Paola; Cova, Umberto

doi:10.1016/0039-128x(93)90028-l

Cited by 14 publications

(6 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Therefore, it was assumed that the instability of 1 was due to the hydroxyl group at C-12. According to literatures (Fantin et al, 1992;Fantin et al, 1993) as well as the results of our experiments, 3-keto group was much more reactive than 7-keto (2, 4, and 5) or 12-keto groups in MeOH solvent, which is easy to be converted to ketal group. However, in the presence of hydroxyl groups at C-7 (6) or C-12 (3, 4, and 6), the conversion of 3-keto group to ketal group was significantly suppressed.…”

Section: Resultsmentioning

confidence: 86%

Bile acid derivatives from a sponge-associated bacterium Psychrobacter sp.

Shinde

Lee

et al. 2009

Arch. Pharm. Res.

View full text Add to dashboard Cite

In our search for bioactive metabolites from a marine sponge-associated bacterium Psychrobacter sp., a new bile acid derivative (1), which was assumed to be an artifact, were isolated along with six known (2-7) compounds by bioactivity-guided fractionation. Elucidation of the structure of the new compound was done using a combination of NMR ((1)H, (13)C, HMBC, HSQC, and COSY) and MS spectroscopy. Compound 1 exhibited moderate suppressive effects on both NO and IL-6 production at a concentration of 200 microM (87.3 microg/mL) without significant cytotoxicity against cells. Compounds 2-5 and 7 showed selective inhibitory activity against several human pathogenic bacterial strains at the low concentration of 30 microg/well. In a cytotoxicity evaluation, only compound 7 showed mild cytotoxicity against five human solid tumor cell lines (A-549, SK-OV-3, SK-MEL-2, XF-498, and HCT-15) with ED(50) values in the range of 11-14 microg/mL.

show abstract

Section: Resultsmentioning

confidence: 86%

Bile acid derivatives from a sponge-associated bacterium Psychrobacter sp.

Shinde

Lee

et al. 2009

Arch. Pharm. Res.

View full text Add to dashboard Cite

show abstract

“…3-Keto-7α-hydroxy- (3b), 3-keto-12α-hydroxy- (3f), 3-keto-7,12α-dihydroxy- (3g), 3-keto-7,12α-dihydroxyacetate- (3h), 3,12-diketo-7α-hydroxy-5β-cholan-24-oic acid (6e), 3,7α-dihydroxy-12-keto-5β-cholan-24-oic acid (5c), 3α-hydroxy-7-keto-5β-cholan-24-oic acid (4b), 3,12α-dihydroxy-7-keto-5β-cholan-24-oic acid (4c), 3α-hydroxy-12-keto-5β-cholan-24-oic acid (5b), and 3α-hydroxy-7,12-diketo-5β-cholan-24-oic acid (6f) 30 were prepared and characterized according to recently described procedures. − …”

Section: Methodsmentioning

confidence: 99%

Improved Enantioselectivity in the Epoxidation of Cinnamic Acid Derivatives with Dioxiranes from Keto Bile Acids

et al. 2002

Self Cite

View full text Add to dashboard Cite

show abstract

“…Compounds (I), (II) and (III) were prepared and characterized according to recently described procedures (Dean et al, 1999;Bortolini et al, 1996;Fantin et al, 1993). Compound Molecular packing diagram of the layer structure of CA, including the guest molecules G trapped within lipophilic channels.…”

Section: Synthesesmentioning

confidence: 99%

Hydrogen-bonded aggregations of oxo-cholic acids

Bertolasi¹,

Ferretti²,

Pretto³

et al. 2005

Acta Crystallogr Sect B

Self Cite

View full text Add to dashboard Cite

The crystal structures of six new crystals of oxo-cholic acids (oxo-CA) are reported: (I) 3alpha,12alpha-dihydroxy-7-oxo-5beta-cholan-24-oic acid; (II) 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oic acid; (III) 7alpha-hydroxy-3,12-dioxo-5beta-cholan-24-oic acid; (IV-alpha) and (IV-beta) 12alpha-hydroxy-3,7-dioxo-5beta-cholan-24-oic acid; (V) 3,7,12-trihydroxy-5beta-cholan-24-oic acid. (IV-beta) is a pseudopolymorphic solvated form of (IV-alpha) and contains small channels which can trap disordered water molecules. In all the structures the four saturated cycles, forming the common alicyclic skeleton, have the same conformation, while the carboxylic side chain adopts flexible conformations in order to produce the most efficient crystal aggregations. The structures display a variety of supramolecular architectures dominated by networks of cooperative O-H...O hydrogen bonds forming different packing motifs often supported by weaker C-H...O interactions.

show abstract

Synthesis of 7- and 12-hydroxy- and 7,12-dihydroxy-3-keto-5β-cholan-24-oic acids by reduction of 3,7-, 3,12- and 3,7,12-oxo derivatives

Cited by 14 publications

References 10 publications

Bile acid derivatives from a sponge-associated bacterium Psychrobacter sp.

Bile acid derivatives from a sponge-associated bacterium Psychrobacter sp.

Improved Enantioselectivity in the Epoxidation of Cinnamic Acid Derivatives with Dioxiranes from Keto Bile Acids

Hydrogen-bonded aggregations of oxo-cholic acids

Contact Info

Product

Resources

About