Synthesis and Cytotoxic Activity of a New Family of α-Hydroxyphosphonates with the Benzothiophene Scaffold
Mátyás Milen, Tamás Miklós John, Anna Sára Kis, Zsófia Garádi, Zsuzsanna Szalai, Angéla Takács, László Kőhidai, Konstantin Karaghiosoff, György Keglevich
TL;DR
This paper reports the synthesis of new α-hydroxyphosphonate compounds with benzothiophene and tests their ability to kill cancer cells.
Contribution
A new family of α-hydroxyphosphonates with benzothiophene was synthesized and shown to have significant cytotoxic activity.
Findings
Most of the synthesized α-hydroxyphosphonates showed significant cytotoxic activity against various cancer cell lines.
Compounds with a trifluoromethyl group in the benzene ring exhibited the strongest cytotoxic effects.
Single-crystal X-ray analysis confirmed the structure of one compound.
Abstract
Background: α-Hydroxyphosphonates, one of the most prominent classes of phosphonates, remain of utmost importance because of their potential and real biological activity as pharmaceutical or pesticide agents. The effect is the consequence of their enzyme inhibitory properties. Objectives: It was planned to make available new heterocyclic hydroxyphosphonate derivatives with cytotoxic activity. Methods: After optimizing the synthesis, 23 members of a new family, α-hydroxy-α-(benzothiophen-2-yl)-methylphosphonates, were prepared by the Pudovik reaction of benzo[b]thiophene-2-carboxaldehydes and diethyl phosphite. The addition was performed at 26 °C in the presence of triethylamine as the catalyst. One of the products was also characterized by single-crystal X-ray analysis. Results: The cytotoxic effect of the α-hydroxy-α-benzothiophenyl-methylphosphonates was tested on U266 myeloma, A2058…
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Taxonomy
TopicsOrganophosphorus compounds synthesis · Synthesis and Reactivity of Sulfur-Containing Compounds · Phosphorus compounds and reactions