Synthesis and evaluation of the anticancer activity of some semisynthetic derivatives of rutaecarpine and evodiamine

Abstract

The synthesis and anticancer activity evaluation of new quinazoline alkaloids rutaecarpine and evodiamine semisynthetic derivatives and their molecular hybrids with lupinine moiety is described. Newly synthesized compounds were elucidated based on elemental analyses and spectral data (¹H and ¹³C NMR). Anticancer cytotoxicity was studied toward some cell lines of lung cancer, T-lymphoblastic leukemia, colon cancer, myeloid leukemia, and osteosarcoma. Among the tested compounds, the highest activity with a specific sensitivity profile toward the Leukemia cell lines CCRF-CEM and K-562 was demonstrated by the starting compound evodiamine. Structural modifications of the studied quinazoline alkaloids did not lead to the improvement of anticancer activity.

Graphical Abstract

Keywords:

• Anticancer activity
• quinazoline alkaloids
• quinolizidine alkaloids
• semisynthetic derivatives

Additional information

Funding

The work was supported by the grant of the Czech Ministry of Education, Youth and Sports [CZ-OPENSCREEN – LM2018130 and EATRIS-CZ – LM2018133] and internal grant of Palacky University [IGA_LF_2020_019].