A new approach to steroid dimers and macrocycles by the reaction of 3-chlorocarbonyl derivatives of bile acids with O,O-, N,N-, and S,S-dinucleophiles

Steroidal Conjugates: Synthesis, Spectroscopic, and Biological Studies

“…The 3-chlorocarbonyl derivatives of lithocholic and cholic acid esters, were prepared by reactions of the respective 3a-alcohol with triphosgene (Cl 3 COCO-OCCl 3 ) in methylene chloride in the presence of catalytic amounts of pyridine [26]. The reaction of chloroformate with 1,2-dihydroxybenzene or N,N'-dinucleophiles with a two, three, or four unit linker in THF with pyridine, sodium hydride, and 4-dimethylaminopyridine (DMAP) as the base gave bis-carbonate (101) and (102-106), respectively.…”

“…The dimers of bile acid esters linked bis-carbamate (101), bis-carbonate (102-105), and bis-monothiocarbonate (106) [26]. of formation were determined by PM3 semiempirical method.…”

“…They play a very important role in supramolecular chemistry and as drugs in pharmacology [16,17]. Bile acid dimers can be used for the synthesis of macrocyclic compounds as artificial receptors [22][23][24][25][26]. SCHEME 6.1 Biosynthesis of primary (6,7), secondary (4,5), and conjugated bile acids (4a-7b).…”

Spectroscopic methods and theoretical studies of bromoacetic substituted derivatives of bile acids

“…[13][14][15][16] Bile acid dimers can be used for the synthesis of macrocyclic compounds as artificial receptors. [19][20][21][22][23] Some derivatives of bile acids are very good organogelators. [24][25][26] The above mentioned applications of bile acids make them very interesting and promising materials.…”

Synthesis and Spectroscopic Characterisation of O-Chlorocarbonyl Derivatives of Bile Acid Methyl Esters

“…[7][8][9][10][11][12] We have shown recently that 3-O-chlorocarbonyl derivatives of bile acid esters are suitable substrates for the efficient preparation of a novel type of head-to-head bile acid dimers bearing a biscarbamate, bis-carbonate, or bis-monothiocarbonate moieties in the spacer group. 13 Thus, the reaction of the steroidal chloroformate esters with O,O-, N,N-, and S,S-dinucleophiles gave high yields of dimers which could be further transformed to macrocyclic compounds, as potential synthetic ligands.…”