Synthesis, antiproliferative and antibacterial evaluation of C-ring modified colchicine analogues

•10 novel amine derivatives of colchicine were synthesized.•Obtained compounds showed potent antiproliferative activity against cancer cells.•Some of compounds showed antibacterial activity.

A series of 10 amine derivatives of colchicine have been obtained with high yields by modification at C(10)-OCH3 position of C-ring and characterized by spectroscopic methods. In vitro cytotoxicity has been evaluated against four human tumour cell lines (HL-60, HL-60/vinc, LoVo, LoVo/DX), as well as antibacterial activity against clinical isolates of methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus epidermidis (MRSE). From among the compounds tested the most active is colchicine derivative 2h with bis(2-methoxyethyl)amine substituent which is active in nanomolar to submicromolar concentrations and is several times more cytotoxic than cisplatin and doxorubicin. This compound is also effective against the methicillin-resistant Staphylococci strains.

Graphical abstractThe most cytotoxic compounds are active in nanomolar to submicromolar concentrations.Figure optionsDownload full-size imageDownload as PowerPoint slide