651323-32-9Relevant academic research and scientific papers
Facile Synthesis, Aggregation Behavior, and Cholesterol Solubilization Ability of Avicholic Acid
Mukhopadhyay, Samrat,Maitra, Uday
, p. 31 - 34 (2004)
(Equation presented) Avicholic acid, a major constituent of the bile of several avian species, was synthesized in eight steps from readily available chenodeoxycholic acid in 9% overall yield using Breslow's remote functionalization strategy in a key step. Micelle formation and equilibrium cholesterol solubilization properties were studied for avicholate in aqueous solution.
Avicholic acid: A lead compound from birds on the route to potent TGR5 modulators
Pellicciari, Roberto,Gioiello, Antimo,Sabbatini, Paola,Venturoni, Francesco,Nuti, Roberto,Colliva, Carolina,Rizzo, Giovanni,Adorini, Luciano,Pruzanski, Mark,Roda, Aldo,MacChiarulo, Antonio
supporting information; experimental part, p. 273 - 277 (2012/06/01)
Grounding on our former 3D QSAR studies, a knowledge-based screen of natural bile acids from diverse animal species has led to the identification of avicholic acid as a selective but weak TGR5 agonist. Chemical modifications of this compound resulted in the disclosure of 6α-ethyl-16-epi-avicholic acid that shows enhanced potency at TGR5 and FXR receptors. The synthesis, biological appraisals, and structure-activity relationships of this series of compounds are herein described. Moreover, a thorough physicochemical characterization of 6α-ethyl-16-epi-avicholic acid as compared to naturally occurring bile acids is reported and discussed.
