N-Silylmethyl-2-(1-Naphthyl)Acetamides: Synthesis, Structure and Computational Screening

Abstract

Synthesis of new hybrid organosilicon compounds based on the amides 1-naphthylacetic acid was described. N-Organyl-2-(1-naphthyl)-N-[(triethoxysilyl) methyl]acetamides were obtained by the reaction of 1- naphthylacetyl chloride with α-silylamines RNHCH2Si(OEt)3 (R = Me, i-Pr and Ph). Their subsequent interaction with N(CH2CH2OH)3 led to the formation of N-organyl-2-(1-naphthyl)-N-(silatranylmethy) acetamides. The structure of these hybrid compounds wascharacterized by 1H, 13C, and 29Si NMR spectroscopy. The structure of N-methyl- and N-isopropyl-2-(1-naphthyl)-N-(silatranylmethy)acetamides was confirmed by X-ray diffraction analysis. Results of computational screening showed that these silatranes are bioavailable and have drug-likeness. Silatranes XSi(OCHRCH2)3N belong to a widely known class of pentacoordinated silicon compounds with intramolecular dative bond Si←N. Their unique structure in combination with properties of the X substituent provide high and diverse physiological and pharmacological activities: immunomodulatory, antitumor, growth stimulating, antimicrobial and other]. Over the last 15 years, several papers have been published on the study of growth-regulating activity of compounds containing silatranyl group. However, there is no systematic study of phytohormones containing the silicon group in the molecule. N-organyl-2-(1-naphthyl)-N-(silylmethyl)acetamides NMR spectroscopy, X-ray diffraction analysis, computational screening, PASS, ADME