New 3-Aminopropylsilatrane Derivatives: Synthesis, Structure, Properties, and Biological Activity

Abstract

The biologically active compound 3-aminopropylsilatrane (a compound with a pentacoordinated silicon atom) underwent an aza-Michael reaction with various acrylates and other Michael acceptors. Depending on the molar ratio, the reaction yielded Michael mono- or diadducts (11 examples) containing functional groups (silatranyl, carbonyl, nitrile, amino, etc.). These compounds were characterized via IR and NMR spectroscopy, mass spectrometry, X-ray diffraction, and elemental analysis. Calculations (using in silico, PASS, and SwissADMET online software) revealed that the functionalized (hybrid) silatranes were bioavailable, druglike compounds that exhibited pronounced antineoplastic and macrophage-colony-stimulating activity. The in vitro effect of silatranes on the growth of pathogenic bacteria (Listeria, Staphylococcus, and Yersinia) was studied. It was found that the synthesized compounds exerted inhibitory and stimulating effects in high and low concentrations, respectively.

New Functional Alkoxysilanes and Silatranes: Synthesis, Structure, Properties, and Possible Applications

“…1 H-NMR (CDCl 3 , 400 MHz), δ (ppm): 0.58 (m, 2H, SiCH 2 ); 1.14 (t, J = 7.0 Hz, 9H, CH 3 ); 1.52 (m, 2H, CH 2 ); 2.43 (t, 2H, CH 2 N); 2.56 (t, 2H, NCH 2 ); 2.84 (t, 2H, CH 2 ); 3.73 (q, J = 7.0 Hz, 6H, OCH 2 ). 13 Silatranes 9-14 have been described in [44].…”

Intrinsic dynamic and static natures of APn--X+--BPn σ(3c–4e) type interactions (APn = BPn = N, P, As and Sb; X = H, F, Cl, Br and I) in bicyclo[3.3.3] and bicyclo[4.4.4] systems and their behaviour, elucidated with QTAIM dual functional analysis

“…14–17 Thus, the skeletons of I and II could supply the diverse electronic structures and have unique functionalities, such as superbase, 18–20 catalysis 21–23 and biological activity. 24–27 Alder and coworkers synthesized various derivatives of I and II and related species. 9,11,28–31 1,5-Diazabicyclo[3.3.3]undecane ( 1 ) 28 and 1,6-diazabicyclo[4.4.4]tetradecane ( 5 ) 29 are the typical examples.…”