Novel approach to bis(indolyl)methanes: De novo synthesis of 1-hydroxyiminomethyl derivatives with anti-cancer properties

• Unprecedented synthesis of bis(indolyl)methane oximes.
• Substitution pattern of the starting oximes and/or indoles allows easy structural modulation.
• Synthetic strategy enables the construction of a vast library of new compounds.
• Anti-cancer activity and selectivity against leukaemia and lymphoma cell lines.
• Promising role of bis(indolyl)methanes for the therapy of leukaemia and lymphoma.

A versatile and broad range approach to previously unknown bis(indolyl)methane oximes based on two consecutive hetero Diels–Alder cycloaddition reactions of electrophilic conjugated nitrosoalkenes with indoles is disclosed. The cytotoxic properties and selectivity of some adducts against several human cancer cell lines pointing to a promising role in the development of anti-tumoural drugs, in particular for leukaemia and lymphoma.

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