The synthesis,content determination and stability study of a β-carboline-cinnamic acid skeleton compound B4
GUAN Li
CHEN Jia-xin
SONG Peng-fei
ZHAO Hui-ru
XIA Yan-xin
ZHANG Sheng-jie
LI Wei-ze
Abstract：Objective:To synthesize the β-carboline-cinnamic acid skeleton compound B4,a new method for its determination was established and the stability and hemolytic characteristic of B4 were evaluated.Methods:β-Carboline was synthesized by the Pictet-Spengler reaction using tryptamine as the raw material.Subsequently,the β-carboline-cinnamic acid compound B4 was synthesized by the condensation reaction of β-carboline and 4-chlorocinnamic acid.Compound B4 was qualitatively and quantitatively analyzed by HPLC,with optimization of chromatographic conditions performed alongside methodological verification.The stability of compound B4 in simulated gastric and intestinal fluid was assessed using this detection method.The hemolytic evaluation of compound B4 was conducted in accordance with the relevant provisions of the hemolytic and coagulation test method.Results:The structural determination of compound B4 was conducted using 1 H-NMR,13 C-NMR,and ESI-MS.The optimal chromatographic conditions were established as:YMC-Pack ODS-A column(250 mm×4.6 mm,5 μm),with a mobile phase of methanol and water at V(methanol):V(water)of 90:10,employing iso-degree elution at a flow rate of 1.0 mL·min-1 and detection wavelength of 278 nm.The linear range of the method was 1～100μg·mL-1.The linear equation was y=126.96x+199.85(R2=0.999 4).And the average recovery rate was 104％.The methanol solution of the compound remained stable for at least 24 h at 25℃.Compound B4 was unstable in acidic artificial gastric fluid where it rapidly degraded,while it was relatively stable and slowly degraded in artificial intestinal fluid until it was completely degraded after 150 min.At the same time,the hemolytic test of the compound B4 showed no visible hemolysis and coagulation phenomenon,thereby complying with the relevant provisions of pharmacopoeia.Conclusion:A method for content determination of compound B4 was established,which is a newly synthesized innovative small molecule.B4 exhibits greater stability in alkaline solution than in acidic solution.
Keywords：β-carboline-cinnamic acid compoundsynthesiscontent determinationHPLCartificial gastrointestinal fluidhemolysis test
Publication Date：2025-04-15
Online Publishing Date：2026-08-14(First online date of this platform, not the publication date of the document)
Pages：7( 771-777 )