E. M. Gibadullina, T. H. B. Nguyen, T. T. Nguyen, A. G. Strelnik, A. D. Voloshina, A. P. Lyubina, S. K. Amerhanova, A. R. Burilov, “Synthesis of new <i>p</i>-quinone methide containing morpholine fragment: access to (diarylmethyl)phosphonamidates with antitumor activity”, Mendeleev Commun., 2023, Volume 33, Issue 2,Pages <nobr>234

Communications

Synthesis of new p-quinone methide containing morpholine fragment: access to (diarylmethyl)phosphonamidates with antitumor activity

E. M. Gibadullina^a, T. H. B. Nguyen^b, T. T. Nguyen^b, A. G. Strelnik^a, A. D. Voloshina^a, A. P. Lyubina^a, S. K. Amerhanova^a, A. R. Burilov^a

^a A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russian Federation
^b Kazan National Research Technological University, Kazan, Russian Federation

Abstract: Novel (diarylmethyl)phosphonamidates containing 2,6-di-tert-butylphenol and heterocycle moieties were synthesized by 1,6-conjugate addition of phosphorylated p-quinone methide with morpholine fragment to 2,6-diaminopyridine or 1,3-diaminobenzene. In the case of an acid-catalyzed reaction of p-quinone methide with sesamol, morpholine was cleaved to form 1,2-benzoxaphosphole substituent. Cytotoxic effects of starting compounds and obtained products were evaluated towards human cancer and normal cells.

Keywords: phosphonamidates, p-quinone methides, 1 6-conjugate addition, (diarylmethyl)phosphonamidates, 1 2-benzoxaphospholes, cytotoxicity, antitumour activity.

Language: English

DOI: 10.1016/j.mencom.2023.02.027

	*Supplementary materials:*
		Supplementary_data_1.pdf	1.5 Mb