O- and S-containing 1-azadiene derivatives of 3-aminopropylsilatrane

Адамович, С. Н.; Ushakov, Igor А.; Afonin, A. V.; Вчисло, Надежда В.; Оборина, Е. Н.; Павлов, Д. В.

doi:10.1007/s11172-021-3100-z

Cited by 1 publication

(1 citation statement)

References 33 publications

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“…The high antitumor activity was observed for 1-(β-cyanoethyl)silatrane, 1-vinylsilatrane, and N-γ-(silatrane-1-yl)propyl-Nallylthiocarbamide [10]. Other classes of silatrane derivatives were developed by the chemical transformation of attached amino groups, yielding imino (Schiff base) silatranes [11][12][13][14] or silatrane-1H-pyrrole-2-carboxamide [13], silatranes bearing the aryl(hetaryl)-substituted 1-azadienyl moiety [15], organosilatranes coupled with ferrocene through triazole [16], benzoyl substituted aminopropyl silatranes [17], or a ruthenium complex containing silatrane functional group [18], as promising building blocks for the design and synthesis of advanced materials and pharmaceuticals. These findings have evidenced that the silatrane scaffold-like structure offers multiple targets to exert its functionality and properties.…”

Section: Introductionmentioning

confidence: 99%

Chemical Attachment of 5-Nitrosalicylaldimine Motif to Silatrane Resulting in an Organic–Inorganic Structure with High Medicinal Significance

Zaltariov¹,

Turtoi

Peptanariu³

et al. 2022

Pharmaceutics

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Two chemical motifs of interest for medicinal chemistry, silatrane as 1-(3-aminopropyl) silatrane (SIL M), and nitro group attached in position 5 to salicylaldehyde, are coupled in a new structure, 1-(3-{[(2-hydroxy-5-nitrophenyl)methylidene]amino}propyl)silatrane (SIL-BS), through an azomethine moiety, also known as a versatile pharmacophore. The high purity isolated compound was structurally characterized by an elemental, spectral, and single crystal X-ray diffraction analysis. Given the structural premises for being a biologically active compound, different specific techniques and protocols have been used to evaluate their in vitro hydrolytic stability in simulated physiological conditions, the cytotoxicity on two cancer cell lines (HepG2 and MCF7), and protein binding ability—with a major role in drug ADME (Absorption, Distribution, Metabolism and Excretion), in parallel with those of the SIL M. While the latter had a good biocompatibility, the nitro-silatrane derivative, SIL-BS, exhibited a higher cytotoxic activity on HepG2 and MCF7 cell lines, performance assigned, among others, to the known capacity of the nitro group to promote a specific cytotoxicity by a “activation by reduction” mechanism. Both compounds exhibited increased bio- and muco-adhesiveness, which can favor an optimized therapeutic effect by increased drug permeation and residence time in tumor location. Additional benefits of these compounds have been demonstrated by their antimicrobial activity on several fungi and bacteria species. Molecular docking computations on Human Serum Albumin (HSA) and MPRO COVID-19 protease demonstrated their potential in the development of new drugs for combined therapy.

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