23848-46-6Relevant articles and documents
Specific Interactions between Sodium Deoxycholate and its Water-Insoluble Analogues. Mechanisms for Premicelle and Micelle Formation of Sodium Deoxycholate
Kano, Koji,Tatemoto, Shinichi,Hashimoto, Shizunobu
, p. 966 - 970 (1991)
Interactions between sodium deoxycholate (NaDC, host) and its water-insoluble analogues (guests) have been studied in water (pH 10) to clarify the mechanisms for the premicelle and micelle formation of NaDC.Turbidity measurements have been used as a convenient method to study the interactions between the guest and host molecules.At least two α-hydroxy groups attached to the C-3 and C-12 positions of a steroid nucleus are required for the guest steroids to interact with NaDC below the critical micelle concentration.This strongly suggests the formation of a hydrogen-bonded dimer of NaDC as a premicelle whose formation is assisted by the hydrophobic environment provided by the α-plane of the steroid.The guest steroids having a hydroxy group at the C-3 position and a polar head group at the C-24 position, which can participate in hydrogen bonding, are solubilized by the NaDC micelles.The results support the mechanism for the NaDC micelle formation involving hydrogen bonding between the C-3 hydroxy group of a premicelle and the C-24 carboxylate anion of another premicelle.
Rapid Deoxyfluorination of Alcohols with N-Tosyl-4-chlorobenzenesulfonimidoyl Fluoride (SulfoxFluor) at Room Temperature
Guo, Junkai,Kuang, Cuiwen,Rong, Jian,Li, Lingchun,Ni, Chuanfa,Hu, Jinbo
supporting information, p. 7259 - 7264 (2019/05/10)
The deoxyfluorination of alcohols is a fundamentally important approach to access alkyl fluorides, and thus the development of shelf-stable, easy-to-handle, fluorine-economical, and highly selective deoxyfluorination reagents is highly desired. This work describes the development of a crystalline compound, N-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor), as a novel deoxyfluorination reagent that possesses all of the aforementioned merits, which is rare in the arena of deoxyfluorination. Endowed by the multi-dimensional modulating ability of the sulfonimidoyl group, SulfoxFluor is superior to 2-pyridinesulfonyl fluoride (PyFluor) in fluorination rate, and is also superior to perfluorobutanesulfonyl fluoride (PBSF) in fluorine-economy. Its reaction with alcohols not only tolerates a wide range of functionalities including the more sterically hindered alcoholic hydroxyl groups, but also exhibits high fluorination/elimination selectivity. Because SulfoxFluor can be easily prepared from inexpensive materials and can be safely handled without special techniques, it promises to serve as a practical deoxyfluorination reagent for the synthesis of various alkyl fluorides.
Modification on ursodeoxycholic acid (UDCA) scaffold. Discovery of bile acid derivatives as selective agonists of cell-surface G-protein coupled bile acid receptor 1 (GP-BAR1)
Sepe, Valentina,Renga, Barbara,Festa, Carmen,Damore, Claudio,Masullo, Dario,Cipriani, Sabrina,Di Leva, Francesco Saverio,Monti, Maria Chiara,Novellino, Ettore,Limongelli, Vittorio,Zampella, Angela,Fiorucci, Stefano
, p. 7687 - 7701 (2014/12/12)
Bile acids are signaling molecules interacting with the nuclear receptor FXR and the G-protein coupled receptor 1 (GP-BAR1/TGR5). GP-BAR1 is a promising pharmacological target for the treatment of steatohepatitis, type 2 diabetes, and obesity. Endogenous bile acids and currently available semisynthetic bile acids are poorly selective toward GP-BAR1 and FXR. Thus, in the present study we have investigated around the structure of UDCA, a clinically used bile acid devoid of FXR agonist activity, to develop a large family of side chain modified 3,7 dihydroxyl cholanoids that selectively activate GP-BAR1. In vivo and in vitro pharmacological evaluation demonstrated that administration of compound 16 selectively increases the expression of pro-glucagon 1, a GP-BAR1 target, in the small intestine, while it had no effect on FXR target genes in the liver. Further, compound 16 results in a significant reshaping of bile acid pool in a rodent model of cholestasis. These data demonstrate that UDCA is a useful scaffold to generate novel and selective steroidal ligands for GP-BAR1.
