Interaction of anisole with 3α-hydroxy-5β-cholan-24-oic acid macrolides. Part 1. Comparative 1H NMR spectral investigation

Bile Acids as Building Blocks of Supramolecular Hosts

“…Cyclocholates are macrocyclic polyesters (macrolactones) with two to six steroid units formed by head-to-tail cyclization of the bile acids. The most general procedure for the synthesis of these cyclic oligomers has been to prepare them from monomeric or linear dimeric derivatives of bile acids by modified Yamaguchi macrolactonization [ 52 ] using DCBC (2,6-dichlorobenzoyl chloride) and DMAP (4- N , N -dimethylaminopyridine) as coupling reagents ( Scheme 1 ) [ 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 ]. Gao and Dias have reported [ 62 ] the macrolactonization of lithocholic acid using DCC (dicyclohexylcarbodiimide) instead of DCBC in cyclization process.…”

“…Lappalainen et al . have studied molecular recognition properties of cyclic cholanoates by the 1 H NMR titration method using anisole [ 53 ] and ferrocene [ 55 ] as guest. The 7α- and 12α-trifluoroacetoxy substituted cholanoate triolides showed clear molecular recognition properties towards anisole and the formation of 1:2 adducts between ferrocene and cyclic triolides were also observed.…”

Macrocyclic bile acids: from molecular recognition to degradable biomaterial building blocks

“…59 This may be due to side reactions, despite the use of unsubstituted lithocholic acid derivatives, and to a less favourable conformation of the dimer prior to cyclisation, as compared to head-to-tail types of structures. Indeed, as demonstrated by theoretical works, [60][61][62] head-to-head dimers can adopt a variety of conformations depending on their linker. Some of these conformations are relatively open and do not favour cyclisation with short rigid spacers at the C3-positions.…”

“…49 Similarly, Kolehmainen and coworkers showed that 7a-and 12a-trifluoroacetyloxy-substituted lithocholate triolides bind anisol with relatively modest association constants (logK <1.5). 62 Finally, the complexation of triply bridged steroidal cyclophanes prepared by Kohmoto et al with a series of analytes was studied. 89 Relatively modest binding constants were measured, possibly reflecting the substantial degree of freedom of these cyclophanes.…”

Synthesis of Nitrogen‐ and Oxygen‐Containing Macrocycles—Derivatives of Lithocholic Acid

“…[2] A number of such macrocycles were obtained by using 2,6-dichlorobenzoyl chloride or dicyclohexylcarbodiimide and 4-N,N-dimethylaminopyridine. [3][4][5][6][7][8][9][10] Cyclocholeates were shown to be macrocyclic molecules with adjustable cavity size for trapping polar molecules of different geometry and dimensions. [7] Brady and Sanders elaborated another approach to the synthesis of cyclodimers based on transesterification reactions, called "living" macrolactonization.…”