Obtaining symmetric and asymmetric bisphosphoramidates and bisphosphoramidothioates by a single step multicomponent reaction

Abstract

We present a new single-step multicomponent reaction strategy for the synthesis of symmetric and (novel) asymmetric bisphosphoramidate and bisphosphoramidothioate derivatives. Reactions proceed under routine experimental conditions, do not require the aid of any catalyst, and provide moderate yields after a short time. We synthesized 18 different compounds, 10 of them for the first time. The cytotoxic activity of our adducts was assessed by measuring their inhibitory capacity (IC₅₀) against two different cell lines, the A549 (lung cancer cells) and the SW1353 (chondrosarcoma cells).

Graphical Abstract

Keywords:

• Multicomponent reaction
• bisphosphoramidates
• bisphosphoramidothioates
• symmetric and asymmetric derivatives
• cytotoxicity
• double addition–elimination

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This study was supported by Secretaría de Investigación y Posgrado del Instituto Politécnico Nacional (SIP-IPN), for financial support (Grant Nos. 20195476 and 20200192).