Synthesis of phosphorylated derivatives of isatin with sterically hindered phenol fragments

ABSTRACT

The synthesis of N-[dimethoxyphosphoryl-(3,5-di-tert-butyl-4-hydroxyphenyl)] methylisatins has been performed by the addition of isatin and 5-butylisatin to the double bond of dimethyl-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadienylidene)methylphosphonate. Subsequent functionalization of the compounds synthesized with thiosemicarbazide hydrochloride, 3-(3′,5′-di-tert-butyl-4′-hydroxyphenyl)propionic acid hydrazide, and isonicotinic acid. Hydrazide gave isatin derivatives containing several pharmacophore fragments. Each of them has the ability to the increase the antioxidant and biological activities of these compounds.

GRAPHICAL ABSTRACT

KEYWORDS:

• Isatin
• phosphonate
• sterically hindered phenol
• antioxidants

Funding

The work was supported by the Russian Foundation for Basic Research (grant No. 15-43-02088-а).