2097-89-4Relevant articles and documents
Haemolytic activity of formyl- and acetyl-derivatives of bile acids and their gramine salts
Kozanecka-Okupnik, Weronika,Jasiewicz, Beata,Pospieszny, Tomasz,Matuszak, Monika,Mrówczyńska, Lucyna
, p. 50 - 56 (2017)
Bile acids (lithocholic: LCA, deoxycholic: DCA and cholic: CA) and their formyl- and acetyl-derivatives can be used as starting material in chemical synthesis of compounds with different biological activity strongly depended on their chemical structures. Our previous studies showed that biological activity of bile acids salts with gramine toward human erythrocytes was significantly different from the activity of bile acids alone. Moreover, gramine effectively modified the membrane perturbing activity of other steroids. As a continuation of our work, the haemolytic activity of formyl- and acetyl-substituet bile acids as well as their gramine salts was studied in vitro. The structures of new compounds were confirmed by spectral (NMR, FT-IR) analysis, mass spectrometry (ESI-MS) as well as PM5 semiempirical methods. The results shown that the haemolytic activity of formyl- and acetyl-LCA and DCA was significantly higher in comparison with their native forms at the whole concentration range. At high concentration, formyl derivative of CA was as effective as LCA and DCA derivatives whereas at lower concentration its haemolytic activity was at the level of original acid. The acetyl-CA was not active as membrane perturbing agents. Furthermore, gramine significantly decreased the membrane-perturbing activity of hydrophobic bile acids derivatives. The results obtained with the cellular system are in line with physicochemical calculation.
Synthesis and spectroscopic studies of new bile acid derivatives linked by a 1,2,3-triazole ring
Pospieszny, Tomasz,Ma?ecka, Izabela,Paryzek, Zdzis?aw
, p. 301 - 305 (2012)
A novel method for the synthesis of cholic acid derivatives has been developed using 'click chemistry'. Intermolecular 1,3-dipolar cycloaddition of the propargyl ester and azide groups of 3α-azidoacetoxy-7α, 12α-diformyloxy-5β-cholan-24-oate gave a new dimer and oligomer linked by a 1,2,3-triazole ring. The structures of the products were confirmed by spectral (1H NMR, 13C NMR, and FT-IR) analysis, mass spectrometry and PM5 semiempirical methods. Estimation of the pharmacotherapeutic potential has been accomplished for the synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASSs).
The preparation of bile acid amines and oxazolines. II. The synthesis of the amides and oxazolines of ursodeoxycholic acid, deoxycholic acid, hyodeoxycholic acid and cholic acid
Cohen,May,McSherry,Mosbach
, p. 701 - 711 (1982)
Bile acid amides and oxazolines were synthesized by a sequence of steps involving the reaction of the free bile acid with formic acid to yield the formyloxy derivative, preparation of the formyloxy acid chloride, condensation of the acid chloride with 2-amino-2-methyl-1-propanol to give the amide and, finally, cyclization of the amide with thionyl chloride to give the oxazoline. The oxazolines were characterized by physical constants, thin layer and gas-liquid chromatography and identified by elemental analysis and gas-liquid chromatography-mass spectrometry. Some of the bile acid oxazoline derivatives alter the activity of bacterial 7-dehydroxylases in vitro, and inhibit the growth of certain anaerobic bacteria in pure culture.
Recognition of a flavin analogue by novel bile acid-based receptors: Effects of hydrogen bonding and aromatic π-stacking interactions
Muwal, Pradeep Kumar,Chhatra, Rajesh Kumar,Das, Shubhajit,Pandey, Pramod S.
, p. 1263 - 1268 (2017)
Molecular recognition properties are reported for novel bile acid-based receptors that incorporate 2,6-diaminopyridine as a recognition unit. Apart from hydrogen-bonding interactions, the bile acid receptors exhibit significant aromatic π-stacking interactions with the aromatic fused ring of the flavin derivative. These studies provide rationalisation for the differences in binding behaviour of bile acid receptors having differing aromatic arm lengths towards a flavin analogue.
A Scalable stereoselective synthesis of scymnol
Adhikari, Raju,Cundy, Darren J.,Francis, Craig L.,Gebara-Coghlan, Mariana,Krywult, Beata,Lubin, Carolyn,Simpson, Gregory W.,Yang, Qi
, p. 34 - 38 (2005)
A high-yielding, stereoselective synthesis of scymnol 1 has been carried out in five steps starting from commercially available cholic acid 2. The synthesis was designed with the aim of eventual large-scale processing. Triformyloxycholic acid chloride 4 was treated with the magnesium enolate of diethyl malonate to afford the β-keto diester, diethyl 3α,7α, 12α-triformyloxy-24-oxo-5β-cholestane-26,27-dioate 5. The key step in the synthesis was the stereoselective hydroganation of β-keto diester 5 to give the corresponding β-hydroxy diester 6 using a BINAP nithenium(n) catalyst. Subsequent reduction of the diester moiety and deprotection of the hydroxyl groups afforded scymnol 1.
Azobenzene-bridged bile acid dimers: An interesting class of conjugates with conformation-controlled bioactivity
Li, Weina,Li, Yan,Yin, Xianpeng,Liang, Yun,Li, Jian,Wang, Chen,Lan, Yue,Wang, Hui,Ju, Yong,Li, Guangtao
supporting information, p. 2539 - 2543 (2016/05/24)
The synergetic combination of the distinct properties of azobenzene and bile acid could afford stable tweezer-like conformation with tunable hydrophilic and hydrophobic channels, thus increasing their antimicrobial activity toward both Gram-positive and Gram-negative bacteria, which can be conveniently switched off when the conformation turn back to the extended state.
