Facile synthesis of 5 β-cholane-sym-triazine conjugates starting from metforminand bile acid methyl esters: Liquid and solid state NMR characterization andsingle crystal structure of lithocholyl triazine

摘要

Four bile acid-triazine conjugates: N'~2,N'~2-dimethyl-6'-(3α-hydroxy-5β-24-norcholyl)-1',3',5'-triazine-2',4'-diamine (lithocholyl triazine, 4a), N'~2,2-dimethyl-6'-(3α,7α-dihydroxy-5β-24-norcholyl)-1',3',5'-triazine-2',4'-diamine (chenodeoxycholyl triazine, 4b), N'~2,2-dimethy1-6'6'-(3α,12a-dihydroxy-5β-24-norcholyl)-1',3',5'-triazine-2',4'-diamine (deoxycholyl triazine) (4c), and N'~2,N'~2-dimethyl-6'-(3α,7α,12α-trihydroxy-5β-24-norcholyl)-1',3',5'-triazine-2',4'-diamine (cholyl triazine) (4d) have been preparedand characterized by liquid and solid state NMR. An improved synthetic method produced better yieldsand an easier purification procedure for 4d than reported in the literature. Single crystal structure of 4a isreported: empirical formula C_(28)H_(47)N_5O, monoclinic P2_1 space group with unit cell dimensions,a18.7135(5)A, b 7.4510(2) A, c 19.3073(5) A, β 95.7290(10)°, volume 2678.65(12) A~3.