113301-20-5

Usage

Main Properties

1. Synthetic bile acid derivative
2. Potentially effective in treating liver disease and cholestasis
3. Modification of ursodeoxycholic acid
4. Exhibits enhanced hepatoprotective and choleretic effects
5. Anti-inflammatory and immunomodulatory properties
6. Potential for reducing bile duct injury and fibrosis
7. Therapeutic potential for liver diseases and cholestasis

Specific Content

23-methylursodeoxycholic acid shows potential in treating liver disease and cholestasis.
It is a modification of ursodeoxycholic acid.
The compound has enhanced hepatoprotective and choleretic effects compared to its parent compound.
It has anti-inflammatory and immunomodulatory properties, beneficial for liver diseases with inflammation and immune dysregulation.
Additionally, it has shown promise in reducing bile duct injury and fibrosis.
Overall, it holds potential as a therapeutic agent for liver diseases and cholestasis.

InChI:InChI=1/C25H42O4/c1-14(11-15(2)23(28)29)18-5-6-19-22-20(8-10-25(18,19)4)24(3)9-7-17(26)12-16(24)13-21(22)27/h14-22,26-27H,5-13H2,1-4H3,(H,28,29)/t14-,15?,16+,17-,18-,19+,20+,21+,22+,24+,25-/m1/s1

Upstream product

• 1041045-72-0 methyl 23(R,S)-methyl-3α,7α-dihydroxy-5β-cholan-24-oate 
• 91788-59-9 methyl 3α,7α-ditetrahydropyran-2'-yloxy-5β-cholan-24-oate 

Relevant academic research and scientific papers

Nongenomic actions of bile acids. Synthesis and preliminary characterization of 23- and 6,23-alkyl-substituted bile acid derivatives as selective modulators for the G-protein coupled receptor TGR5

23-Alkyl-substituted and 6,23-alkyl-disubstituted derivatives of chenodeoxycholic acid are identified as potent and selective agonists of TGR5, a G-protein coupled receptor for bile acids (BAs). In particular, we show that methylation at the C-23(S) position of natural BAs confers a marked selectivity for TGR5 over FXR, while the 6α-alkyl substitution increases the potency at both receptors. The present results allow for the first time a pharmacological differentiation of genomic versus nongenomic effects mediated by BA derivatives.

BILE ACID ANALOG TGR5 AGONISTS

Provided herein are bile acid analogues and derivatives, methods of synthesizing bile acid analogues and derivatives and their use in treating diabetes and liver disease.

TGR5 MODULATORS AND METHODS OF USE THEROF

The invention relates to compounds of Formula A: or a salt, solvate, hydrate, or prodrug thereof. The compounds of Formula A are TGR5 modulators useful for the treatment of various diseases, including metabolic disease, inflammatory disease, liver disease, autoimmune disease, cardiac disease, kidney disease, cancer, and gastrointestinal disease.

TGR5 modulators and methods of use thereof

The invention relates to compounds of Formula I: or a pharmaceutically effective salt, solvate, hydrate, or prodrug thereof, wherein: R1 is hydrogen, hydroxy, or halogen; R2 is hydrogen or α-hydroxy; R3 is hydroxy, NH(CH2)mSO3H, or NH(CH2)nCO2H; R4 is hydrogen, alkyl, or halogen; R5 is unsubstituted or substituted alkyl, or aryl; R6 is hydrogen or R5 and R6 taken together with the carbons to which they are attached form a ring of size 3, 4, 5, or 6 atoms; m is an integer 0, 1, 2, 3, 4, or 5, and n is an integer 0, 1, 2, 3, 4, or 5. The compounds of Formula I are TGR5 modulators useful for the treatment of various diseases.

Derivatives of biliary acids, process for the production thereof and corresponding pharmaceutical compositions

New derivatives of chenodeoxycholic, ursodeoxycholic, cholic and ursocholic acids, bearing a methyl group in the side chain, in an alfa position to the carboxylic group, the corresponding nor- and di-nor- derivatives, and the corresponding conjugates with taurine and glycine, are described. The compounds of the invention are prepared by methylation of the esters with methyl iodide in the presence of lithium-dialkylamides.